Spectroscopy Practice Problems

Problem 1
IR Spectrum
(liquid film) 1718
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 43
Mass Spectrum
0.5 CIl
o
80 .>t:. co
'"
CIl
0-
'"

0
60 CIl til
..c UV Spectrum
til
M+"
40 '5
'"
..c 29 72 1.0 '"
33.3 mg/10 ml
20 * 1.0 cm cell
Y C4H aO
1.5
solvent: ethanol
40 80 120 160 200 240 280 200 250 300 350

m/e A. (nm)
I I I I I I I I I I I
13C NMR Spectrum

(50.0 MHz, CDCI 3 solution)
II II
LlLillL
solvent I
--J --
proton coupled
proton decoupled
I III
I I I I I I I I I I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(200 MHz, CDCI 3 solution)
TMS
1.
90
Problem 2
IR Spectrum
(liquid film) 1715
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

80 -"
co
Q)
c.
60 Q) 45 No significant uv
Vl
co M+"
.0
74 absorption above 220 nm
40 '0
57

20
I, j C3 H 602
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

(50.0 MHz. COCI 3 solution)
I
DEPT CH 3t CHt
proton decoupled
200
I I I
160
I I
120
I
solvent
80
I

I I
40
U I I
0 o(ppm)
1H NMR Spectrum
(200 MHz. COCI 3 solution)
exchanges
with 0 20

A
r---
12 11
TMS
--1
I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
9
r Problem 3
IR Spectrum
(liquid film) 2984
1741 1243
4000 3000 2000 1600 1200 800 0.0

V (crn")
100 Mass Spectrum

43 0.5
80 "'"
'"0- Q)
60 Q)
(/) UV spectrum
40
'"
.a
'0 29 1.0 solvent: ethanol
Q'!. M+"= 88 15.4 mg /10 mls
20 path length: 1.00 cm
,I I C4Ha02
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum

(50.0 MHz, CDCI3 solution)
DEPT CH 2 t

Ll
proton decoupled solvent

III Il
200 160 120 80 40 0 () (ppm)
1H NMR Spectrum
(200 MHz, CDCI3 solution)
TMS
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
92
Problem 4
,
c,
IR Spectrum 1744
(CCI4 solution)
4000 3000 2000 1600 1200 800

V (cm'")
100 57
Mass Spectrum
29
80 .><
Ctl
Q)
Co
60 Q)
en
No significant UV
Ctl
J::J
M+" = 88 absorption above 220 nm
40 '0
*'
20
I
40 80 120 160 200 240 280
m/e
13C NMR Spectrum
(100,0 MHz, COCl a solution)
DEPT CH2 t CHat CHt

I I

I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(200 MHz, COCl a solution)
expansion
2.0
,
10 ppm
I TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
93
Problem 5
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

27
107/109
80 "''""
Q)
0-
60 Q)
en
No significant UV
'"
.c absorption above 220 nm
40 '0 M+"

20 186/188/190
.11 ,I, C2 H4 Br2
40 80 120 160 200 240 280

mle
13C NMR Spectrum

proton coupled
solvent
I
proton decoupled
I o(ppm)
200 160 120 80 40 0
1H NMR Spectrum
TMS
l'
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
94
Problem 6
IR Spectrum
(liquid film)
1716
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum UV Spectrum

43
80 ""
'"0.
Ql
60 CIlQl
40 '0
'"
.0 solvent: methanol
0
M+' =86
20
I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton decoupled
,
solvent
200 160 120 80 40 o s (ppm)
1H NMR Spectrum
TMS
I
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
95
Problem 7
IR Spectrum 2249
(KBr disc)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum
80 "'" 53
'"
Q)
o,
60 Q)
Ul
No significant UV
40
40 '0
'"
.I:l
M+" = 80 absorption above 220 nm
'#.
20
1
40 80 120 160 200 240 280
m/e
13C NMR Spectrum
I
proton decoupled
- - - ' - - -
solvent L
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS .
I I I I I I I I I 1
10 9 8 7 6 5 4 3 2 1 o
o(ppm)"
96
Problem 8
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (em")
100 Mass Spectrum
80 .,., 57
'"a.
<J)
60 <J)
Ul
No significant UV
'"
.."
absorption above 220 nm
40 '0 M+" =114 1%)
*-
20 99
II I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
(50.0 MHz, CDC'3 solution)

I
I I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(200 MHz, CDC'3 solution)
TMS
I
I I I I I , I I I I I
10 9 8 7 6 5 4 3 2 1 0
o (ppm)
97
Problem 9
3458
IR Spectrum
(CCI4 solution)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

59
80 -'"
to
Q>
0-
60 Q> No significant UV
'"
to
.a
40 '0
M+' =118 1%)
20 *
,I J
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

proton decoupled

200 160 120 80 40 0 S (ppm)
1H NMR Spectrum
(200 MHz, CDCI 3 solution) .. :
:<

,;,',
;:>
Exchanges with ..
2
s,"

"'
S- TMS
I 1
I I I I I I I I I -.1._
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
;
98
Problem 10
IR Spectrum
(KBrdisc) 1693
4000 3000 2000 1600 1200 800

V (cm'")
100 56 Mass Spectrum

M+' = 112
80 """Q)
'"
0-
60 Q)
VI
No significant UV
'"
.J:J
40 '0
0
20
," I,
40 80 120 160 200 240 280

m/e
13e NMR Spectrum

proton decoupled
solvent
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
99
Problem 11
IR Spectrum
(liquid film) 1738
4000 3000 2000 1600 1200 800

V (crn")
100 Mass Spectrum
80
Ql
o, M+' = 84
60 No significant UV
'"
.0
40 '0
<J.
20
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

n
proton decoupled
200 160 120

solvent
80
U
40 0 o(ppm)
..
1H NMR Spectrum expansion

2.2 1.8 PPM TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
100
Problem 12
IR Spectrum
(Ijquidfilm)
4000 3000 2000 1600 1200 800 0.0

V (ern")
Mass Spectrum 0.5

Ql
<J
80
C
'"
<ll
0.
M+"= 156
-e'"0 UV spectrum
60 <ll
III III
..c
'"
..c
127 1.0 '" 5.00 mg 110 mls
40 '0 29 path length: 0.50 cm
<t- contains a haloQen
solvent: cyclohexane
20
II
1.5
40 80 120 160 200 240 280 200 250 300 350
role A(nm)
13C NMR Spectrum No TMS in

solvent
proton coupled
i
proton decoupled
III L
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
Problem 13
2989
IR Spectrum
(liquid film) 689
4000 3000 2000 1600 1200 800

V (cm'")

80 -"
''""
0-
60 '" VJ
No significant UV
'"
.0
40 '0
83 M+'
20 *' 981100/102
I.. II l, JJ C2 H4 CI2
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

proton coupled
61. . . . 1.... , i' "U III f t ... 1IIIf'-........ 'J t ' ....
'. , "P' 4'...... 'LU... 'A roc
. ,i" ....
solvent
proton decoupled
ru I
200 160 120 80 40 0 " (ppm)
1H NMR Spectrum
(200 MHz, CDCJ3 solution)
L expansions
, , ,
-
,

6.0 5.8 ppm 2.2 2.0 ppm
I I I I
=:f I I I I

I I

TMS
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
102
Problem 14
IR Spectrum
(liquid film)
3354
4000 3000 2000 1600 1200 800

V (ern")

80 -'"
C1l
Q)
0-
60 Q)
Vl
No significant UV
C1l
.0
40 '0
?ft.-.
M+' =60 1%)
20 59
JIIHI I C 3H aO
40 80 120 160 200 240 280

m/e
solvent
proton decoupled

200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(200 MHz. CDCI 3 solution)
expansions
I I I , TMS
4.5 4.0 ppm 1.5 1.0 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
103
r>. " 0 ('r 1\ Problem 15
IR Spectrum
(liquid film)
I I I
4000 3000 2000 1600 1200 600

V (cm" )

80 .><
'"
Q)
o,
60 Q)
1Il No significant UV
40
'"
.0
'0 absorption above 220 nm
M+"
20 *' 122/124
,I 1I. II C 3 H 7Br
40 80 120 160 200 240 260
m/e
I I I I I I I I I I I r
13C NMR Spectrum
DEPT CH 2 , CH 3t CHt
solvent
proton decoupled
I
I I I I I I , I I I , I
200 160 120 80 40 0 s (ppm)
1H NMR Spectrum
expansions
1.\.,
-
, , , , , , , , I , TMS
4.6 4.0 ppm 2.0 1.4 ppm -
Ill. I
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
104
Problem 16
IR Spectrum
(liquid film) 776
2960
650
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

55
80
CD
a.
60 5l No significant UV
co
.0 41 absorption above 220 nm
401-'0 M+" 126/128/130 < 1%

201-
40 80 120 160 200 240 280

m/e
I I I I I I I I I I I r
13CNMR Spectrum I
(50.0 MHz, CDCI 3 solution) I H-C-H
H-C-H
I
I
solvent
proton decoupled

200 160 120 80 40 o 8 (ppm)
1H NMR Spectrum
expansions
TMS
I
ppm ppm
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
105
Problem 17
763
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

41
80 -"
<ll
Ql
o,
121/123 No significant UV
60 Ql
III
<ll M+"= 200/202/204
.0 absorption above 220 nm
40 '0

20
". II IJ
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
(100.0 MHz, CDCI3 solution) DEPT CH3t CHt
solvent
proton decoupled
I
Problem 18
IR Spectrum 766
(liquid film) 2960
650
4000 3000 2000 1600 1200 800

V (cm'")

-
80
Ql
c-
.c
<0 77
M+- absorption above 220 nm
40 '0
'#... 156/158/160
20
j ,11
79
107/109
II III C3H6BrCI
40 80 120 160 200 240 280

m/e
I
13C NMR Spectrum H-C-H
I
(50.0 MHz, CDCI 3 solution) I I
H-C-H H-C-H
I I
solvent
/
proton decoupled

200 160 120 80 40 0 o(ppm)

1H NMR Spectr um
expansions TMS
-, r , , , , I
, , , --------'
, , I
L
, , , , I
4.0 3.5 ppm 2.5 2.0 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
107
Problem 19
1H NMR Spectrum
expansion
J
,-- -)
I I I I I
1
I I
J i
34 3.0 2.6 2.2 ppm
TMS
- - --i
1
'-'
I l
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
108
Problem 20
IR Spectrum
1620
(KBrdisc)
4000 3000 2000 1600 1200 800

V (em")

80 "''""
Q)
c.
60 Q)
<Il
No significant UV
'"
.Q
40 '0
#,
20
Ii
40 80 120 160 200 240 280
m/e
13C NMR Spectrum
(100.0 MHz, 020 solution)
I
I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(400 MHz, 020 solution)
Note: there are 3 protons
which exchange with
the 020 solvent
H 20 and HOD
in solvent
3.9 3.7 ppm 1.6 1.4 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
109
Problem 21
IR Spectrum
1600
(KBr disc)
4000 3000 2000 1600

V (crn'")
80 ""co
Q)
c,
60 Q) No significant UV
en
co
40 '0
;f!.
20
40 80 120 160 200 240 280

m/e
13C NMR
Spectrum
(100.0 MHz,
O2 solution)
..........,1.'.' ".OJ : ...,/.".' ......." ....... h, I 4 .... t ,cart. WIU"M ,
..... ,
proton decoupled
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
H 2 0 and HOD
which exchange with in solvent
the 020 solvent .. I
expansions
i i
J , i
3.2 3.0 ppm 2.2 2.0 ppm
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
110
I1 \ Problem 22
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

M+' 108
80 .:.:
ell
<Il
Cl.
Amax 269 nm (I091QE 3.2)
78
60 <Il
Vl
ell
.0
solvent: methanol
40 '0
<fi. 93
20 j j, l C 7H aO
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

lJJ
proton decoupled
200 160
W 120
solvent
80

40 0 o(ppm)
1H NMR Spectrum
expansion
TMS
i i
7.2 7.0
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
III
Problem 23
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'") UV Spectrum
100 79 Mass Spectrum Amax 243 nm (10910 1.9)
80 "" Amax 248 nm (10910 2.1)

<Il'"
0.
Amax 252 nm (10910 2.2)
60 <Il
en
40 15
'"
J:J
Amax 258 nm (10910 2.3)
91
*-
20 Amax 264 nm (10910 2.1)
Amax 268nm (10910 1.9)
80 120 160 200 240 280 solvent: ethanol
40
m/e
13C NMR Spectrum

I I
129 128 127 ppm
solvent
I I I I
proton decoupled 129 128 127 ppm
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(400 MHz. CDCI3 solution)
expansion
Exchanges with
2
j TMS
7.6 7.4 7.2 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
112
Problem 24
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (cm'")
100 Mass Spectrum

91 0.5 II)
o
c:
80 -"
11l 11l
II)
a.
0
60 UV spectrum
II)
'"
.Cl
'"
11l 11l
0.917 mg 110 mls
40
.Cl
'0
1.0
path length: 0.20 cm
'#
20 M+' solvent: hexane
I ,\, .n 170/172
C 7H 7Br
1.5
40 80 120 160 200 240 280 200 250 300 350
mle A. (nm)
I I I I I I I I

13C NMR Spectrum expansion
I i I
140 130 ppm

expansion
I i I
140 130 ppm

I I I I I I I I I
200 160 120 80 40 o s (ppm)
1H NMR Spectrum
r-
TMS
t I
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
113
r
Problem 25
2251
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

M+" = 117
80 .><
'"'"
0- 77
60 '"
'"
'"
.0
40 '0

20
40 80 120 160 200 240 280

m/e
I I I I I I I I r T T I
expansion
13C NMR Spectrum
i i i
130 129 ppm
DEPT CH z' CH 3t CHt expansion

I

do
i i
129 ppm solvent
proton decoupled
I I
200 160 120 80 40 0 s (ppm)
1H NMR Spectrum
I---
TMS
-
1
I I I I
J I I I I I
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
114
Problem 26
3290
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (cm'")
Mass Spectrum UV Spectrum

100
M+" 107
80 ""c-
lIJ
Amax 256 nm 2.2)
Ql
60 Ql
'"
lIJ
Amax 264 nm 2.1)

40 '0 solvent: ethanol

oF- 91
-J, 20
J
" J .1. C 7H g N
40 80 120 160 200 240 280

role

13C NMR Spectrum
1 I
129 128 127 ppm
DEPT CH 2 1CHJ CHt
I
solvent

proton decoupled
1 I 1
I I
129 128 127 ppm
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
(400 MHz, CDCI 3 solution) Exchanges with
D20
expansion
1
TMS
7.6 7.4 7.2 ppm
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
115
Problem 27
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (om")
100 91 Mass Spectrum 0.5

80 -'"
<lI
Q)
0.
60 Q) 92
1I)
<lI UV spectrum
.0
1.0
40 '0 M+'= 122 5.662 mg I 10 mls
;f?
20
I, J ,I I CaH 100 solvent: ethanol
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
I I I
13C
(100.0 MHz,
NMR Spectrum expansion
i ,
li- ,
CDCI 3 solution) 135 130 ppm
I
DEPT CH2 f CH 3t CHt
I
proton decoupled
'::lL 135
,
130
, ,
ppm
solvent
f
I
, , I I I
I
, I I -,
200 160 120 80 40 0 () (ppm)
expansion expansion
lH NMR Spectrum

expansion
3.9 3.8 ppm 2.9 2.8 ppm
7.3 7.2 ppm Exchanges

with D20
TMS

10 9 8 7 6 5 4 3 2 1 o
s (ppm)
116
Problem 28
3325
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (crn")
100 104 Mass Spectrum 0.5 8

80 .>< c
III
III
Co

o
60 Ql
Ul
Ul
.Q
III 77 78 III
.Q 107 1.0 UV spectrum
79
40 '0
<fi. M+'= 122 5.815 mg/10mls
.1 j I. .1. .1 C 8 H 10O solvent: ethanol
1.5 u...................."'-o..J.................. ...L...".................l..o..I...I
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum
(100.0 MHz, COCI 3 solution)
solvent
proton decoupled
I
.
I
200 160 120 80 40 o s (ppm)
1H NMR Spectrum
(400 MHz, COCI 3 solution) expansions
expansion
II
l
i i i i i i i
5.0 4.8 ppm 1.6 1.4 ppm

Exchanges
i i i
with 02
ppm r-
7.5 7.3
L TMS
---'

I
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
117
Problem 29
IR Spectrum
(liquid film) 1715
4000 3000 2000 1600 1200 800 0.0

V (crn")
100 Mass Spectrum

43 0.5 Ql
o
80 -" c
'"
Ql
Co e'"
0
60 Ql
UJ
91 UJ
.J:J
UV spectrum
40
'"
.J:J
'0
1.0 '" solvent: cyclohexane
M+' 7.90 mg 110 mls
;ft. 134 path length: 0.50 cm
20
II ,I II I. C g H 1Q O
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum

DEPT CH2 1 CH 3t CHt

II I
proton decoupled
...-J solvent
II I
I I I I I I I I I
200 160 120 80 40 0 <5 (ppm)
1H NMR Spectrum
..-

TMS
L
10 9 8 7 6 5 4 3 2 1 o
<5 (ppm)
118
Problem 30
IR Spectrum
(liquid film)
1690
4000 3000 2000 1600 1200 800

V (crn'")

77 0.5
80
Q)
c-
60
40
'"
.c
'0
M+" 1.0 UV spectrum
134 1.075 mg /10 mls
<;e.
path length: 0.10cm
20
solvent: ethanol
IJ 1 Cg H 1Q O
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13e NMR Spectrum

solvent
off-resonance decoupled
200 160 120 80 40 0 15 (ppm)
1H NMR Spectrum
I
TMS
10

9
I I
8
I
7
I
6
I
5
I
4
L
I
3
J I
2
L1 0
v;
15 (ppm)
119
Problem 31
IR Spectrum
(liquid film) 1723
4000 3000 2000 1600 1200 800

V (em")
100 Mass Spectrum

105
80 .><
'0-"
Q)
60 Q)
Vl
'"
D
40 '0 77 M+-
134
20
,II L .,li J I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

solvent
II
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
I
9.7
i
9.5
I
3.7 3.5
I
JI
1.5
I
1.3 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
120
Problem 32
IR Spectrum
(liquid film) 1686
4000 3000 2000 1600 1200 800

V (ern")
100 105 Mass Spectrum UV Spectrum 0
80 .><
<ll 77
(lJ
0- Amax 241 nm (10910 4.1)
60 Q)
en M+"
<ll
.0 148
40 '0 solvent: methanol
;/i. 120
20
.1. Ju ,I ,I. II I. C1QH 12O
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

(50.0 MHz. CDCI 3 solution)
I I
proton decoupled 135 130 ppm
1 I
..---- solvent
Iii I
I I I 1 I I I 1 1 1 I I
200 160 120 80 40 o 8 (ppm)
1H NMR Spectrum
, ,
3.0 2.0 1.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
121
Problem 33
IR Spectrum
(liquid film) 1735
4000 3000 2000 1600 1200 800

V (ern")

57
80 "''Q"">
c,
60 Q> No significant UV
til
'"
40 '0

20 M+' 158<1%
I J
40 80 120 160 200 240 280
m/e
I I I I I I I I r I I I
13C NMR Spectrum

solvent
I.
proton decoupled
I I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
- --
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
122
Problem 34
IR spectrum
(liquid film)
, r
1725
4000 3000 2000 1600 1200 800

V (ern")

29 45
80
4l
a. No significant UV
60 Sl
t1I
J::J
M+' absorption above 210 nm
40 0 74
20
III I J.
C3H602
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

(50,0 MHz, CDCI 3 solution)
proto" . . l I
proton _
decoupled
I
_ _ _ _ _ _---il...-
200
I I I
160
I I
120
I
s_"LJ
I
80
I I
40
_
I
L 0
I
o(ppm)
1H NMR Spectrum
TMS
expansion 4x
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
123
Problem 35
IR Spectrum
(KBr disc)
1662
4000 3000 2000 1600 1200 800

V (ern")
100 105 Mass Spectrum UV Spectrum

80 sc
til
ll)
c.
77
Amax 258 nm (Io910E 4.2)
60 ll)
,JJ
VI
til
..0
a
Amax 330 nm (Io910E 2.8)
40
20 *' M+" Amax 388 nm (I091OE 2.2)

210
C14H1002 solvent: ethanol
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

I
Problem 36
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

91 0.5 Q)
o
c
80 ..>< t'lI
t'lI
Q)
0.
-e0
60 Q)
(I)
(I)
.0
t'lI M+" t'lI
.0
162 1.0 uv spectrum
40 '0
165.3 mg 1100 mls

path length: 0.2 cm
20
I ,I I, C14H 14 solvent: ethanol
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum - - Resolves into

two signals at higher fielel
I
DEPT CH 2 f CHJ CHt
- - Resolves into
two signals at higher fielel
proton elecoupled solvent

I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
_ _ _ _ _ _-----' \'-- " .....
I
------l
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
125
Problem 37
3310
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

106
80 -'"
C1l
Ql
0..
60 Ql
'"
C1l
.0
M+'
40 0 197
<ft.
20
C 14H1SN
40 80 120 160 200 240 280

m/e
NMR Spectrum
Jl:i
13C
Sion
(100.0 MHz, COCI3 solution)
, ,
129 128 ppm
DEPT CH z 1CH 3t CHt

JL:LSion
i ,
129 128 ppm
proton decoupled
I solvent
.
I I
200 160 120 80 40 o s(ppm)
lH NMR Spectrum
(200 MHz, COCI 3 solution)
r
exchanges

with O2
-r TMS
I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
126
Problem 38
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200

V (ern")
80 -'"
.,0-<1l
60 ., III
No significant UV
<1l
.0
40 '0
'ffl"
20 M+" = 116
72
I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
1
,,,100 decoupled
1----1----------------1-1
I I I 1 I
J L
1 I
_
I
o () (ppm)
200 160 120 80 40
1H NMR Spectrum
expansion
2.4 2.2 2.0 ppm TMS
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
127
Problem 39
IR Spectrum 1713
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

43 0.5 Gl
u
80 -'" co
''""
0-
-e0'"
60 '"
III
III
..c
40
'"
..c
'0
1.0 '" UV spectrum
99 104.1 mg/10 mls

oR- M+' path length: 0.2 cm
20 114
C S H 1Q 0 solvent: ethanol
.1 .1 ' I. I I
2
1.5
40 80 120 160 200 240 280 200 250 300 350
mle A. (nm)
13C NMR Spectrum

I
H-C-H
I
-CH
3
JC
proton decoupled
solvent TMS
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
128
Problem 40
IR Spectrum
(liquid film)
1746
1259
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

29
80 -'"
'"c-
Q)
45
60 Q)
<1l
No significant UV
'"
.0
M+'= 118 1%) absorption above 220 nm
40 '0
*-
20
,I j C S H 100 3
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

DEPT CH2 CH3t CHt

I
proton decoupled
200
I I I
160
I I
120
I
OOILJ
I
80
I I
40
I
L 0
I
o(ppm)
1H NMR Spectrum
- TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
129
Problem 41
IR Spectrum
(liquid film)
4000 3000 2000 1S00 1200 800

V (cm'")

80 .><
ell
Q)
0.
SO Q)
(J)
ell
..0
40 '0
;f?
74
20
,II I M+' = 130 1%) C S H 1003
40 80 120 1S0 200 240 280
m/e
13C NMR Spectrum

proton coupled
I j II
proton decoupled
I I I I I I I
solvent
I
III
I I
I
I
L I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
..
expansion

L1
,---
, , , , TMS
2.5 2.0 1.5 ppm ----1
-
1
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
130
Problem 42
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

29
80 "'"
<ll
Ql
Co
60 Ql
!Il
<ll
.0
40 (;
'if!.
20 45 M+' = 146 1 %)
,I .I C 6H 10 04
40 80 120 160 200 240 280

m/e
I I I I I I
, I I I I I
13C NMR Spectrum

I
DEPT CH2 ' CH3t CHt
solvent
proton decoupled
I
I I I I
200 160 120 80 40 o 0 (ppm)
J
1H NMR Spectrum
TMS
I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
131
Problem 43
IR Spectrum 1742
(liquid film)
4000 3000 2000 1600 1200 800

V (em")
80
<Il
C.
60 I- 3l No significant UV
III
..c absorption above 220 nm
40 (;
86
20
I M+" = 146 1%)
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton coupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
- TMS
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
132
Problem 44
IR Spectrum
(liquid film) 1739
4000 3000 2000 1600 1200 800

V (ern")
80 "'III"
Q)
c.
UI
III
40 '0 59
'#.
87
20 I- M+" 146 < 1%
.L .I I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

solvent
1

proton decoupled
200 160
,., .... It, t Pi" .t;
120
,J.,
80
:ih ..J....
ll ..........
40
l._.".. . o 0 (ppm)
1H NMR Spectrum
TMS
- -
I I I I I I : I I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
133
Problem 45
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

43
80 -'"
ell
Q)
o,
(/)
ell
40 '0
20 *' 87 M+" = 146 1%)
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

C-H
C
TMS
solvent
proton decoupled
III
j
200 160 120 80 40 o (5 (ppm)
1H NMR Spectrum

-

10 9
I I
8
I
7
.il
I
6
I
5 4
I I
3
I
2
I
1
T 0
(5 (ppm)
134
Problem 46
IR Spectrum
(liquid film)
1737
4000 3000 2000 1600 1200 800

V (ern")
80 -'"
Cll
Ql
Q.
60 Ql No significant UV
'"
Cll
..0 115 absorption above 220 nm
40 '0 87
20 *' M+'
146
C 6 H1Q 0 4
40 80 120 160 200 240 280
mle
TMS
,
.11.
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
135
Problem 47
IR Spectrum
(liquid film) 1747
4000 3000 2000 1600 1200 800

V (ern")
80 -'"
'Co"
Q)
60 Q)
(f)
No significant UV
'"
.D
40 '0 87
;f?
M+'
20 146
IJ,
59
I
I C 6 H1Q 0 4
40 80 120 160 200 240 280
mle
13C NMR Spectrum
DEPT CH z+ CH 3t CHt
I
proton decoupled solvent m
II I
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
expansions
r--"
L

I I I I
"r:
2.5 1.5
J -"
I I I

5.5 4.5 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
136
Problem 48
IR Spectrum
(liquid film) 1736
4000 3000 2000 1600 1200 800

V (em")
100 Mass Spectrum

101
80 "'.,l'll"
60 .,
Q.
129
II>
No significant UV
l'll
.0
40 '0
0>i'!...
20 M+"
,1.1 III Il 1 174
CS H 1404
40 80 120 160 200 240 280
m/e
I I I I I , , I I I I I
13C NMR Spectrum

DEPT t CH
I
CH 2 3t CHt
I
proton decoupled
200
I I
160
I I I
120
I
solvent
80

[
I I
40
LL I I
0 8 (ppm)
1H NMR Spectrum
expansion
I---

--'
- -
, I
4.0 2.0 ppm
TMS
I
10 9 8 7 6 5 4 3 2 1 0
8 (ppm)
137
Problem 49
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

80 .>t:
III
Q)
c-
60 Q)
Ul
III
40 '0 M+"=174 1%)
?ft.
100
20
1,1 I. n C aH 140 4
40 80 120 160 200 240 280

m/e
13C NMR Spectrum


I I I I I 1 I I 1 I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
1_ _ _
TMS
138
Problem 50
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

71
80 .><
70
'C."
Ql
40
'"'"
.c
'0
M+' = 158 1%) absorption above 220 nm
<fl.
20
C aH 1403
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

(50.0 MHz. CDCJ 3 solution)
I
proton decoupled
200
I I I
160
I I
120
I
solvent
80
I
I I
Il
40
I I
o () (ppm)
lH NMR Spectrum
,--
J
1L-JL-
I I
2.00 1.50 ppm TMS
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
139
Problem 51
IR Spectrum
(nujol mull)
4000 3000 2000 1600 1200 800 0.0

V (cm'")
100 Mass Spectrum

0.5 Q)
o
c:
80 "''"" M+"
Q)
c. 234/236/238
'"

0
III
60 Q)
III
155/157
.0 UV spectrum
'"
.0
1.0 '"
40 '0 a 15.07mg/10ml
<f- !! 0.302 mg/10ml
20 C 6 H 4 Br2 path length: 0.5 cm
I I ,L solvent: ethanol
40 80 120 160 200 240 280 250 300 350

m/e A(nm)
13C NMR Spectrum

(20,0 MHz, CDC'3 solution)
I solvent
II
proton decoupled
I
200 160 120 80 40 o o(ppm)
1H NMR Spectrum
TMS
I I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
140
Problem 52
IR Spectrum
(nujol mull)
4000 3000 2000 1600 1200 800

V (ern")

80 -""
l\'l
C12H8Br2
Q)
c- Amax 264 nm (1 09 10 1:: 4.5)
60 Q)
en
l\'l
.Q 76 M+" solvent: methanol
40 15 310/312/314
20 "*
11 ,,-.II L
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

C-H C-H
C C solvent
proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
1 I I I i iii
8.0 7.5 7.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
141
Problem 53
IR Spectrum
(liquid film) 696
4000 3000 2000 1600 1200 800

V (em")
100 125/127 Mass Spectrum

80 """
'a.Q"l
60 rnQl
'"
.0
40 '0
*" M+
20 160/162/164
J,I,h ,L" .l J. 1.1.
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton decoupled
I
SOlve: I
200 160 120 80 40 o o(ppm)
1H NMR Spectrum
expansion
V -,
I I I
B.O 7.5 7.0 6.5 ppm TMS
V 1
I I I I I I I I I I 1-
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
142
Problem 54
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (em")
80
'a."
Q)
60 Q)
III
'"
.0
40 '0
o .
20
I I
40 80 120 160 200 240 280

m/e

13C NMR Spectrum
, , ,
130 128 ppm
t CHt
DEPT CH 2 , CH 3
I

proton decoupled
,
130 128 ppm
, ,
I I
,.
solvent
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
expansion
Jl
7.6 7.4 ppm
.1
JI -
TMS
I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
143
Problem 55
IR Spectrum
(KB'r disc)
3400 1720
4000 3000 2000 1600 1200 800

V (em")
100 105
80 .><
III
'"
Q. Amax 253 nm (10910E 2.6)
60 '" fF)
III
40 '0
.0
M+" =228 1%)
Amax 259 nm (10910E 2.7)
20

Amax 264 nm (l0910E 2.5)
,I. IL I C14H1203 solvent: ethanol
40 80 120 160 200 240 280

m/e
I I I I I I I I I I
13C NMR Spectrum
i i
130 128 ppm
j[''"' OO solvent
, , ,
proton decoupled
I I
130 128 ppm I "j'..-J
200 160 120 80 40 0 S (ppm)
1H NMR Spectrum
(400MHz, CDCI 3 solution)
expansion
Exchanges
with D20

+
Exchanges
JlJl
,
7.7 7.6
,
7.5 ppm
, , , with 020
TMS
14.5 14.0 13.5 ppm
+
----r- 1
I I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
S (ppm)
144
Problem 56
IR Spectrum
(KBrdisc)
3461
3326
4000 3000 2000 1600 1200 800

V (cm-1 )
100 UV Spectrum
Mass Spectrum
M+" 110
80 ""III
Ql
Amax 225 nm (loglOE 3.5)
60
0.
Ql
en
Amax 27S nm (log lOE 3.4)
III
40
.Q
'0 Amax 283 nm (log 10 E 3.3)

"#.,
20
solvent: methanol
J .Ii I I C SHS 0 2
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

I

I I I
11I I I I I I T
.'Ill $' ,....

1M.'n.......
Wl ...
lIIlfIIlIlI.W1_. ..
_ll/l"lWJt#... ..... 1IWI
....-.ll'IoollI_.........
II"," t 'Ifi
r- '"">---- solvent
proton decoupled
I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
expansion
1rr--r-
Exchanges with
0:0
-
S ' 0'90 '
I
i
680 ppm
TMS
10 9 8 7 6 5 4 3 2 1 0
8 (ppm)
145
Problem 57
IR Spectrum
(CCI4 solution)
I I I I I
4000 3000 2000 1600 1200 800

V (ern")

M+- =168
80 "'co"
<IJ
a. 153 Amax 267 nm (Io910E 2.8)
60 <IJ III
co
.0
solvent: ethanol
40 '0
*-
20
I l I C9H1203
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

_ _J"--------J"-------
proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
, ,
7.0 6.4 ppm ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
146
Problem 58
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (cm'")
100 Mass Spectrum

105 0.5 1Il
80 .:s:. M+' <J

c:
'"c-
1Il
120 -eo'"
60 1Il
en
en
.c
40
'"
.c
'0
1.0 '" UV spectrum
*' 5.875 mg 110 mls
20
'I II 1 I, C 9H12
1.5
solvent: ethanol
40 80 120 160 200 240 280 200 250 300 350

mle A(nm)
I I I I I I I I I I
13C NMR Spectrum

I I
proton decoupled
I
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
s
I I I I
L I I I I I I
TMS
I
I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
147
Problem 59
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (em")

80 "'"
'e-" Ql
Amax 261 nm (109101': 2.7)
60 Ql
IJl
'"
J:> Amax 269 nm (109101': 2.5 )
40 '0
'$.
solvent: methanol
20
I I I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

I I
solvent
proton decoupled
I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
"
'.. .
.--

- TMS
I
I I I I I I I I I I L
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
148
Problem 60
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

80 -'"
<1l
Ql
0- Amax 270 nm (109
10
2.6)
60 Ql
VI
<1l
.Q
solvent: methanol
40 '0
.
Q
20
I I I l
40 80 120 160 200 240 280
m/e
I I I I I I I I I I I. I

13C NMR Spectrum
(100.0 MHz. CDCI 3 solution) expan:JL
i I I
135 130 ppm
I I i I I
DEPT CH 2 , CH 3 + CH + 24 20 ppm
" proton decoupled

"''"jill I I I
I I
I i i i
135 130 ppm
III solvent 24 20 ppm
I I I I I I I I I I
200 160 120 80 40 0 8 (ppm)
1H NMR Spectrum
resolves into 2 peaks
at higher field
J.
,.<;
.:."
. +
:1_,:
."{
':
t r--
t i
6.8
i
6.6 ppm 2.2 2.0 ppm

TMS
I ----{ - I
tL
. I I I I I I I I I I I
J.;
10 9 8 7 6 5 4 3 2 1 0
8 (ppm)
149
Problem 61
IR Spectrum
(KBrdisc)
4000 3000 2000 1600 1200 800 0.0

V (crn'")
100 Mass Spectrum

119 0.5 III
<J
c:
80 .><
<1l
Gl
a.
'"

0
60 Gl
III
III
.0
UV spectrum
'"
.0 M+' 1.0 '"
40 '0 134 1.032 mg 110 mls
*" path length: 1.00 cm
20 solvent: cyclohexane
I Ii J. J.. L 1 IJ C 10 H 14
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum
1 III
proton decoupled
I I I I I
lL I I
solvent
I I I I
TMS
j
I
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
-r-
------1
TMS
I I
J 1I
I I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
150
Problem 62
IR Spectrum 802
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
80
III
c-
60
M+"
134
'"
.c
401-0
"#..
20
I II 1, "L [I .t" 1,1
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

solvent
proton decoupled
II I
I I I I I I I I I I , I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
151
Problem 63
IR Spectrum
(liquid film)
4000 3000 2000 1600

V (em")

80 ""'"
Ql
a. M+' = 134 Amax 274 nm (109101': 2.3)
60 Ql
Ul
'"
.t:J Amax 277 nm (109101': 2.3)
40 '0
'#.
20
I I " 1,1
40 80 120 160 200 240 280

m/e
13e NMR Spectrum expansion


expansion
,
i i
140 130 ppm ,

20 15 ppm
J
expansion
solvent , ,
I 20 15
200 160 120 80 40 0 () (ppm)
1H NMR Spectrum
expansion
lr
I-- -= , , , TMS
- 2.2 2.0 ppm
- 1
I I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
() {ppm}
152
Problem 64
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (em")

80 "'III"
Q)
0. Amax 278 nm (109 10 8 2.4)
60 Q)
'"
III
.0 M+' Amax 274 nm (109108 2.4)
40 '0 162
c!?: Amax 270 nm (109108 2.5)
20
solvent: methanol
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton coupled
solvent
200 160 120 80 40 o 3 (ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 0
3 (ppm)
15:
aus .
Problem 65
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

80 ""
'c.." Q)
Amax 232 nm (log lO E 3.4)
60 Vl Q)
'"
.0 Amax 248 nm (log 10E 3.5)
40 '0
20
;f<.
Amax 265 nm (log lO E 3.4)
I II I solvent: isooctane
40 80 120 160 200 240 280

m/e
1:1
13C NMR Spectrum
, , , , ,
15 13 ppm
DEPT CHA CH 3t CHt
proton decoupled
II
solvent

I
[I
, , , ,
15 13
i
ppm
200 160 120 80 40 0 (5 (ppm)
lH NMR Spectrum
(400 MHz, CDC'J solution)
expansion expansion expansion
JL
,
2.7 2.6 ppm
JL
1.85 1.75 ppm

1.3 1.2 ppm
TMS
A L
10 9 8 7 6 5 4 3 2 1 0
(5 (ppm)
154
Problem 66
3348 IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum
80 -" 44
'"Co
Q) 43
M+"
60 Q)
If)
'"
.0
40 '0 absorption above 210 nm

201-
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

(50.0 MHz. COCI3 solution)
proton coupled
proton decoupled
L

200 160 120 80 40 0 () (ppm)
1H NMR Spectrum
exchanges
with 0 20 on warming
/ TMS
I
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
155
Problem 67
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 SOO

V (cm'")

<Il
c,
ctl
.1:J
40 '0

45 61 M+" = 104 1%)
20
. 76 C4H S03
1,1 ,I
40 SO 120 160 200 240 2S0

m/e
I I I I I I I I f I I I
13C NMR Spectrum

j.
solvent
proton decoupled
I I I I I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansions exchanges
with 0 20
t
4.4 4.0 3.6 ppm 1.4 1.2 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
156
Problem 68
2266
IR Spectrum
(liquid film) 1749
4000 3000 2000 1600 1200 800

V (cm")
80 .><
III
II)
c-
60 II)
lJ)
No significant UV
III
.D absorption above 220 nm
40 '0
'ifl. M+'

20 86
113
U I
40 80 120 160 200 240 280

m/e
I I
13C NMR Spectrum

DEPT f
I
CH 2 CHat CHt
solvent
proton decoupled
L I
Problem 69
IR Spectrum
(liquid film)
1714
4000 3000 2000 1600 1200 800

V (ern")

80 -'"
co
<Il 43
Co
60 <Il
lJ)
No strong UV
co
40 '0
M+"
20 *' 88
73
I,JI .1 C4 H a0 2
40 80 120 160 200 240 280
m/e
13e NMR Spectrum
DEPT CH 2 , CH 3t CHt Ij
proton decoupled
I
I
I
200
I
160
I I
120
I I
solvent
80
J I I
40
l I I
0 o(ppm)
1H NMR Spectrum
expansions

, , ,
ppm
, , ,
, exchanges
with 0 20
TMS
4.5 4.0 2.0 ppm

1.5
1
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
158
Problem 70
3410
IR Spectrum
(liquid film) 1705
4000 3000 2000 1600 1200 800

V (ern")

43
80
'"a.cv
60 cv
III
58
'"
.0 M+ = 116 1%) solvent: hexane
40 'i5
20 *'
1.1.1" I, I I,
40 80 120 160 200 240 280

m/e
I I I I I
13C NMR Spectrum

-CH 3
I
H-C-H
I
solvent
- CH 3
C
C
I J
200 160 120 80 40 0 () (ppm)
lH NMR Spectrum
exchanges
with 0 20

-
- -
r-
--' TMS
I I I I I I
- I I I I I
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
159
Problem 71
IR Spectrum 1740
(liquid film)
4000 3000 2000 1S00 1200 800

V (em")
100 Mass Spectrum

43
80 "''""
Q)
0-
SO Q) No significant UV
<I>
40
'"
.0
'0 56
M+' = 116 1%)
*' 73
20
l II .1 CS H 1202
40 80 120 1S0 200 240 280
m/e
I I I I I I I I I I , I
13C NMR Spectrum
DEPT CH 2 CH 3t CHt
solvent
I
proton decoupled
200
I I
160
I I
120
I I
lJ
80
I I I
40
L,I I
0
I
o{ppm}
1H NMR Spectrum
20 HZ
I I
11 I
3.85 ppm

I
1.92 ppm
I
0.93 ppm
1/
expansions at 400 MHz

- !A.
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
160
Problem 72
IR Spectrum
(liquid film) 1709
4000 3000 2000 1600 1200 800

V (crn'")
1001- 57 Mass Spectrum
80 ::.: 59
'"
<U
Co
60 <U
<Jl
No significant UV
40 '0
'"
LJ
J
'#.'.
20 M+'116<1%
I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
solvent
t
proton decoupled
I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
1-
Exchanges with
2
t
Offset ---.J
_ TMS
I I I
11.0 ppm
13.0 12.0
- -
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
161
Problem 73
IR Spectrum
(liquid film)
3376
4000 3000 2000 1600 1200 800

V (em")

80 .><
'"
<ll
C.
60 <ll No significant UV
l/l
til
.c
73
40 '0
20 *' M+" '" 88 1%)

.I .II I C5H12O
40 80 120 160 200 240 280

mle
13C NMR Spectrum
DEPT CH2 , CH 3t CHt
proton decoupled I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
Exchanges with
2
+
TMS
10 9 8 7 6 5 4 3 2 1 o .,
s (ppm)
162
Problem 74
3305
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

f- 30
80
III
Co
<Il
40 '0
?f!.. M+
20 101
,L
j
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

(50.0 MHz, COC'3 solution)
proton decoupled
200 160 120

solvent
80
I WLl
40 0 o(ppm)
2H
1H NMR Spectrum exchange
(200 MHz, COCI 3 solution) with 020
)
G
--- I-
-! TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
163
a 1St
Problem 75
IR Spectrum 1740
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

80 ""
'"
a>
0.
60 a>
rJl
No significant UV
40
'"
..c
'0 107/109
20 *" M+'
180/182
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

solvent
proton decoupled
I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
':0 ' ,', ppm
i ,
4.8 4.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
164
Problem 76
IR Spectrum
(liquid film)
1715
4000 3000 2000 1600 1200 800

V (ern")
80 -'"
'c-a"l 75
60 al
1Il
No significant UV
'"
.0
40 '0
<F-
101 M+'
20
il II .j I 132 CSH 1203
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

-CH 3
I
H-C-H
I
C-H
proton decoupled -CH 3
solvent TMS
C 1 L
200 160 120 80 40 0 o (ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
165
Problem 77
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (ern")
80 ""m
Q)
Co
60 Q)
In
No significant UV
m
40 '0 101

20
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
solvent
;'
proton decoupled
I I I I I I I I
I I I I I
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
(200 MHz. COCI3 solution)

0 with
Ir-
20
----.-/'--
V-
I I
11.0 10.0 ppm
----' -----' TMS
t
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
166
Problem 78
IR Spectrum
(KBr disc)
1729
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

69
41
80 ..l<
<ll 97
Q)
Q.
60 Q)
'"<ll
.Q
40 '0
;je. M+" = 160 1%)
20
j
142 C 7H 1204
1,1 J I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

....... ".)IM!J'A
... .... , ",., ....". tl:Il"l ..,_
dioxan
reference __
67.7 ppm
proton decoupled
II I
200 160 120 80 40 o s (ppm)
dioxan
1H NMR Spectrum reference
(100 MHz, 020 solution) 3.7 ppm 6H
H20 and HOD

in solvent
I .
Note: all labile protons
exchange in the

O2 solvent
2H 2H
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
167
Problem 79
IR Spectrum
(liquid film)
1640
4000 3000 2000 1600 1200 800

V (em")
100 Mass Spectrum

72
80 ..><
co 44
Q)
Co
60 Q)
<Jl
No significant UV
co
.J:J absorption above 220 nm
40 '0

20
l
40 80 120 160 200 240 280
mle
I I I I I I I I I
13C NMR Spectrum

off-resonance decoupJed l I,
proton decoupled solvent TMS

I I
200 160 120 80 40 o 8 (ppm) .
1H NMR Spectrum
TMS
I
I I I I I I I I I I l
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
168
Problem 80
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (em")
100 Mass Spectrum
80 -'"
co
CD
Co
60 CD
VI
No significant UV
co
.0
40 '0

20
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
(100.0 MHz, CDCI 3 solution) DEPT CH 2 , CH 3t CHt
I
proton decoupled
,
solvent
I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
(400 MHz, CDCI 3 solution) expansion expansion
J ,
3.8
i
3.6 ppm 1.8 1.6 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
169
Problem 81
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200

V (ern")
80 -'"
'c,"
Q)
III
'"
40 '0
<f!.
20
1
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

(100.0 MHz, dioxan-D8 solution) DEPT CH 2 ' CH 3t CHt
proton decoupled
200 160 120 80 40 o () (ppm) .
lH NMR Spectrum
(400 MHz, dioxan-D8 solution)
TMS
l
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
170
Problem 82
IR Spectrum
1108
(KBrdisc)
4000 3000 2000 1600 1200 800

V (ern")
100 45 . 89 Mass Spectrum
80 -"
III
Ql
0.
00
III
.Q absorption above 220 nm
40 '0
;je.
20
I
40 80 120 160 200 240 280

m/e
I I I I I T I I I I I T
13C NMR Spectrum
solvent
proton decoupled
L.
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
171
Problem 83
IR Spectrum
(liquidfilm)
4000 3000 2000 1600 1200 800

V (ern")
80 ""'"
60
'a". No significant UV
'"
!Il 39
'"
.0
77
M+'
40 '15
<f!.
, II, 110/112/114
20
1,1 n I, I" C 3 H 4CI 2
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

(50,0 MHz, CDC'3 solution)
proton coupled
solvent
200 160 120 80 40 o 0 (ppm)
1H NMRS pectrum
expansion
1,.--
expansion
with resolution with resolution
enhancement enhancement
-I
5,8
i
.
I
5.4 ppm
I
V- I
4,2
I
4,0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
172
Problem 84
IR Spectrum
(liquid film) 1740
4000 3000 2000 1600 1200 800

V (crn'")
80 -'"
<ll
Q)
0..
60 Q)
VJ
No significant UV
<ll
.0
40 15
73
M+" = 150/152 1%)
20
1.11., I ,I
40 80 120 160 200 240 280
m/e
13e NMR Spectrum

" proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
SF TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
173
Problem 85
IR Spectrum
1720
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

138 140
80 -'"
'"
Ql
0-
Ul
115
'"
40 '0
;f!. M+" = 194/196 1%)
20
IJ" .11 I.
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

I
proton decoupled
200 160 120

solvent
80
I lillL
40 a () (ppm) .
1H NMR Spectrum
"""'0"'
TMS
I I I I
4.5 4.0 2.0 1.0 ppm
- - exchanges
with O2
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
174
Problem 86
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

29 66
80 ...,
ell
<Il
0-
60 <Il
VJ
No significant UV
ell
.0
40 '0
:o!e.
0
M+" = 94 1%)
20
40 80 120 160 200 240 280

m/e
I
13C NMR Spectrum H-C-H
I
C-H
C TMS
solvent
proton decoupled
.U "u ,I
P' "11"
"
200 160 120 80 40 0 o(ppm)
lH NMR Spectrum
J
J
I I I I I I
j I
I I
TMS
I
I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
175
Problem 87
2248
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

43
80 41
40
M+"= 83 1%)
20 68
II .j j
40 80 120 160 200 240 280

role
I I I I J I I I I I I I I
13C NMR Spectrum
m J
l - ' '- _
solvent
proton decoupled
_ _ _ _ _ _ _ _ _ _ _ _ _ _J - -
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum TMS

expansions at 400 MHz 20Hz
JL I
2.26 2.03
I
J I
1.07
10 9 8 7 6 5 4 3 2 1 0
o (ppm)
176
Problem 88
2114
3295
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
1001- 55 82 Mass Spectrum
80 ..><
t'lI
<IJ
Q.
60 <IJ
III
No significant UV
t'lI
40 '0
<fi.
20 M+" = 83
II II
40 80 120 160 200 240 280
m/e
13C NMR Spectrum
I
I
proton decoupled
200
I I
160
I I I
120
I
;O'D
80
I I
III
I
40
I
0
I
o (ppm)
1H NMR Spectrum Exchanges

(400 MHz, COCI3 solution) with 020
expansion
2H 1H 2H 2H
2H
I I II '----
, I I
TMS
2.5 2.0 1.5
I
10 9 8 7 6 5 4 3 2 1 0
o (ppm)
177
b
Problem 89
IR Spectrum
3410 (liquid film)
4000 3000 2000 1600 1200 800

V (em")
100 Mass Spectrum

43
80 -"
'Co"
Ql
60 Ql
VI
No significant UV
'"
J:l
M+' = 86 1%) absorption above 220 nm
40 '0 71

20
III .II .111 C SH1QO
40 80 120 160 200 240 280
m/e
I I I I I I I I I I , T
DC NMR Spectrum
DEPT CH 2 f CH 3t CHt
l
proton decoupled
I solvent I I
I I I I I I I I I I I -,
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
exchanges
I I
with 0 20
6.0 5.5
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
178
Problem 90
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (crn'")
100 57 75 Mass Spectrum
80 ""'-
<0
01l
Co
60 CD No significant UV
U>
<0
Ll
40 '0
';fl.,
20 104 M+"= 119 C4 H gN03
I ,I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

DEPT CH2 f CH3t CHt
proton decoupled
I
200 160 120 80 40 0 (ppm)
1H NMR Spectrum
expansions
l
which exchange with
the 020 solvent
Jl
4.3 4.1 ppm 3.6 3.4 ppm 1.3 1.1 ppm
,-- lr-
H20 and HOD
in solvent
I . - - -
10 9 8 7 6 5 4 3 2 1 0
(ppm)
179
Problem 91
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (em")
100 Mass Spectrum

91 0.5
8c
80
'"'"c. -e0'"
60 <Jl
'"
<Jl .Q
'"
40
'"
.Q
'0
1.0 UV spectrum
*- M+" 5.30 mgl10 mls

20 1981200 path length: 1.00 cm
.I II C 9H 11 Br solvent: cyclohexane
'I I J
.Ii.
1.5
40 80 120 160 200 240 280 200 250 300 350
mle A, (nm)

two signals at higher field
II
DEPT t CH t t
----r'
CH 2 3 CH
- - Resolves into

I i I
solvent
II
proton decoupled 35.0 34.0 ppm
I ..
200 160 120 80 40 o 0 (ppm)

I
3.0 2.5 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
180
Problem 92
IR Spectrum 1553
(liquid film) 1387
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

43 0.5 CD
41 o
80 ..>< c:
OJ OJ
CD
0.

0
60 CD
II)
II)
..0
UV spectrum
OJ OJ
40 '0
..0
1.0 137.0 mg /10 mls
path length: 0.2 ern
o>R. .
M+' = 89 1%)
solvent: ethanol
20
C 3H 7N02
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

DEPT CH 2 CH 3t CHt
proton decoupled
200
I I I
160
I I
120
I
solvent -1
I
80
I
40
I
LI
I I
0 o(ppm)
lH NMR Spectrum
expansion
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
181
Problem 93
1115
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

57
80 ..><
co 29
Ql
0-
'"
co
.c
87
40 '0

73
101 M+"
20
II I
130
I C8H 18O
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

I
proton decoupled
- - - - - - - - - - " - - - - -
I I I I I I
solvent
I I I
UL
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
TMS
3.0 2.0 1.0 PPM
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
182
Problem 94
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

91 0.5 Il>
u
80 -" c:
<1l <1l
Q)
UV spectrum
"'- 92 0
60 Q)
II) .c
II)
1.430mg /10 mls
<1l <1l
.c M+" path length: 2.00 cm
40 '0 1.0
134 solvent: hexane

20
1,1 IJ,.L ,I J l C1QH 14
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum

I
H-C-H
I
I H-C-H
H-C-H I -CH
I 3
expansion
, TMS
130
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
I I
expansions
expansion
I i i i , i
2.8 2.6 1.7 1.6 1.5 1.4 1.1 1.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
183
Problem 95
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

80 1a
Q)
0. Amax 262 nm (lo910E 2.5)
60 :ll
to
.D solvent: ethanol
40 '0
<fl
20 I 77
h II ,I" I I.
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

(50.0 MHz, CDCI 3 solution) expansion
solvent

r I I i r
128 124 ppm
C
proton decoupled
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
I expansion
V-- ppm
\
i
7.4
V
.. j
7.2
c-
- j TMS
I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
184
Problem 96
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

80 .:.<
<tl
Ql
C.
60 Ql
<Il
<tl
.>J
40 '0

20
u I I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
DEPT CH 2 , CH3t CHt

I I
,
/
solvent
proton decoupled
I I I I
I
I I i
I
I
II I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansions expansion
,
7.5 7.3
,
ppm
i
2.8

2.7 ppm
i
1.8
I
1.7 ppm 1.45

i
1.35 ppm
1
1.05
,
0.95
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
185
Problem 97
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

92
80 ""CD'"
0-
91
Amax 260 nm (I0910c 2.5) \
60 CD
U>
'"
.D
solvent: methanol
40 '0
;f!.
M+"
20
I. 1,148
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

(50,0 MHz. CDC'3 solution)
solvent
200 160 120 80 40 o (5 (ppm)
1H NMR Spectrum
expansion
I ,
7,5 7.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
(5 (ppm)
186
Problem 98
IR Spectrum
(liquid film)
4000 3000 2000 11600 1200 800

V (em- )

139/141
80 ""<Ilco
Co
60 <Il
tJl
co
J:J
40 '0 M+'
cf!.. 182/184
20
IJ. ,I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum - - Resolves into two

(50.0 MHz, CDCI 3 solution) signals at higher field strength
DEPT CH z' CH 3t CHt

1
- - Resolves into two
signals at higher field strength
I II
solvent
proton decoupled
I I II
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum

(200 MHz, CDC'3 solution) expansion
j I I
2.75 2.5 ppm 1.5 1.0 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
187
Problem 99
IR Spectrum 1718
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

43
119
80 "''"" ,
(l)
a. Amax 262 nm (I091O E 2.5)
60 (l)
"''"
.c
M+" solvent: methanol
40 '0 176

20
I. II L ,.I.""jll I I.
161 I C 12 H16 0
40 80 120 160 200 240 280

m/e
13e NMR Spectrum


1
I I
130 125 ppm
DEPT CH2 t CH3 t CH t

lc";oo
I
130
I
125 ppm
I
.'
I
proton decoupled
I
solvent
II II
I I I I I J I I I I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
188
Problem 100
1693
IR Spectrum
(CCI4 solution)
4000 3000 2000 1600 1200 800

V (crn'")
100 183/185 Mass Spectrum UV Spectrum

80
ltJ
Ol
c-
60 Ol
(fl
ltJ
.a 155/157
solvent: ethanol
40 0 M+" = 198/200
f1!..
20
1 Il 11 CaH 70Br
40 80 120 160 200 240 2ao

mr e
13C NMR Spectrum

DEPT CH 2 , CH 3+ CH+
proton decoupled
I
solvent
I I II .
200 160 120 80 40 0 () (ppm)
1H NMR Spectrum
(200 MHz, COCI3 solution)
expansion
JJL -
7.8 7.2 ppm
TMS
I
I I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
Problem 101
IR Spectrum
(liquid film)
UV spectrum
0.104 mg/10 mls
solvent: ethanol
250 300 350

A (nm)
13C NMR Spectrum

C-H C-H
-CH
3
l
C CC
proton decoupled TMS
I II I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
(100 MHz, CDCI3 solution) 3H
2H 2H
TMS
I I
1U
I I I I I I I I
I
l
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
190
Problem 102
IR Spectrum 1773 1738 875

(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

119
UV Spectrum
,
80 "'"
Q) ""a.
91
Amax 254 nm (10910 4.3)
60 Q)
'"
""
.0 Amax 258 nm (10910 4.2 )
40 '0
*' Amax 279 nm (10910 3.3)
20 M+" = 1541156
.,1] I, CS H 70CI Amax 290 nm (10910 3.0)
40 80 120 160 200 240 280 solvent: hexane

m/e
L
13C NMR Spectrum

, ,
DEPT CH 2 t CH 3t CHt 132 131 ppm
I
proton decoupled
I I
r. .----J
,
132 131
i i
ppm solvent
I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
expansion
,.-
II ,
8.0
,
7.5
,
7.0 ppm
--'
I TMS
I
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
191
Problem 103
3500-2500
IR Spectrum 1688
(KBrdisc)
4000 3000 2000 1600 1200 800

V (em")
100 135 M+- 152 Mass Spectrum UV Spectrum

80 ""'"
Ql
c-
60 Ql
rJ)
'"
40 '0
oft.
20
I III .111 .1,,1 I .1"
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

DEPT CH2 1 CHat CHt

I I
solvent
LJ
1
proton decoupled
1
200 160 120 80 40 0 o (ppm)
1H NMR Spectrum
expansion
exchanges

with 0 20

JL JL
I
8.1
I I
8.0 7.0
I I I
6.9 ppm
I--
I I
13.0 12.0 r-r-rr: ,---
TMS
----1 .--1 - I
I I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
192
Problem 104
IR Spectrum
(liquid film) 1743
1229
4000 3000 2000 1600 1200 800

V (ern") UV Spectrum
100 Mass Spectrum

108 Amax 252 nm Q0910E 2.2)
80 -'"
<Il
Q)
Amax 257 nm (i0 9 10E 2.3)
c. 91
60 Q)
U>
<Il
43 Amax 262 nm (I0910E 2.2)
.0
40 '15
.
M+" 150 Amax 264 nm (I0910E 2.2)
o
20 Amax 268 nm (I091OE 2.0)

.I .I ,l ,I 1,1. rJ C gH 10 0 2
solvent: ethanol
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

expansion
1L I
128.5
I
128 ppm
proton decoupled
,;'ppm I I
,
solvent
I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
I
7.5
,

I
7.4
I
7.3
,
ppm
----
--.J TMS
- -
I
I I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
193
Problem 105
IR Spectrum
(nujol mull)
1670
4000 3000 2000 1600 1200 800

V (cm")

135
80 -"
co
Q)
a.
M+"
Amax 270 (I091O E 4.2)
60 Q)
'"
co
.0
150 solvent: methanol
40 '0
20 * ..J 107
I I n, Jt.. J I C g H1Q 0 2
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

solvent
l
l
I J .k ,l
",,"0,,10
at 130ppm
,-
TMS
proton decoupled
I I l I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
3H
3H
2H 2H
TMS
U
.,
L
I I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
194
Problem 106
IR Spectrum
(liquid film) 1760
4000 3000 2000 1600 1200 800

V (crn'")

\
80 .><
ttl
<I)
Co Amax 265 nm (109101> 2.6)
60 <I)
VJ
107
ttl
.Q
Amax 271 nm (109101> 2.6 )
40 '0

M+' = 150 solvent: methanol
20
I I J, I
40 80 120 160 200 240 280

m/e
I I I I I I I I I I
13e NMR Spectrum

, , , ,
DEPT t CH
CH2 3t CHt 24 20 ppm
I

, , , ,
proton decoupled
I I I
I
I
I
I
I
I I
solvent
I
I
24
I
20 ppm
I
II I
200 160 120 80 40 0 3 (ppm)
1H NMR Spectrum
expansion
-
7.2 7.0

ppm J d
- TMS
I
I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
3 (ppm)
195
Problem 107
IR Spectrum 1724
(liquid film)
4000 3000 2000 1600 1200 800

V (cm-1 )
80 .><
l'll
Ql
a. Amax 238 nm (109101': 4.2) \
60 Ql
VI
l'll
.Cl
91
Amax 281 nm (109101': 2.7)
40 '0
;f!.
solvent: methanol
20
1.1
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
. JL"":'"'
, , ,
132.5 130.0 ppm
I I
DEPT

CH 2 CH3t CHt
slon
, , , solvent
proton decoupled 132.5 130.0 ppm
I I I-.-J
200 160 120 80 40 0 () (ppm)
1H NMR Spectrum
expansion
L JL
If
8.0 7.9 7.3 7.2 ppm
- TMS
I I I
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
196
Problem 108
IR Spectrum
3352 (liquid film)
4000 3000 2000 1600 1200 800

V (cm'")

80 ""III M+" \
138
Ql
c, Amax 270 nm (109108 3.1)
60 Ql
121
'"
III
.J::J Amax 282 nm (10 9 10 8 3.1)
40 '0
solvent: hexane
20
C8H100 2 Note: UV spectrum not changed
significantly on addition of base
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

I
proton decoupled
I I
200
I
160
I
I I
IU I
120
I
solvent
80
I
I LJ
I
40
I I I
o s (ppm)
1H NMR Spectrum
__ exchanges TMS
with D 20
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
197
Problem 109
IR Spectrum 1085
(CHCI3 solution)
4000 3000 2000 1600 1200 800

V (cm'")

80
'"a.
Ql
60 Ql
VI
'"
.0
Note: UV spectrum changed
40 '0
significantly on addition
oR-
of base
20
III,
40 80 120 160 200 240 280
m/e
I I I I I I I I , I , I
13C NMR Spectrum
DEPT CH2 CH3t CHt

I
I
solvent
proton decoupled
I I I I
I
I I I
'.
I I
I
I , ,
200 160 120 80 40 o s (ppm)
1H NMR Spectrum
Exchanges
with D20
J
.I
II .
7.5
,
7.0
"-
ppm
-
II-
- TMS
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
198
Problem 110
2209
IR Spectrum
(nujol mull)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

145
,
80 "'ro"
Q)
Co
60 Q)
III
102
ro
.Q
40 '0 M+"
20 * 146
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton coupled
Problem 111
IR Spectrum
(KBrdisc)
4000 3000 2000 1600 1200 800 UV Spectrum

V (crn'")
100
Amax 310 nm (I091OE 3.3)
Mass Spectrum
80
Amax 261 nm (I091O E 4.3)
\
Ql 120
a. solvent: methanol
60
M+"
199/201
'"
40 '0
.Q
Amax 262 nm (lo910E 3.0)
20 Amax 257 nm (Io91O E 3.0)

Amax 222 nm (Io91O E 4.0)
40 80 120 160 200 240 280 solvent: methanol 1 HCI

m/e
13C NMR Spectrum

solvent
proton decoupled
I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion with
resolution enhancement
I I
7.5 6.5 ppm
TMS
-
II L
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
200
Problem 112
1666
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

80
4l
0-
60
'"
.0
401-'0
t/!.-,
107
M+"
20
d. j I I
192
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
I
I
I I
I
I I I I I
I
I I I I I
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
(200 MHz, CDCI 3 solution) expansion
I I I I
8.0 7.5 7.0 6.5 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
201
Problem 113
IR Spectrum
(liquid film) 1766
4000 3000 2000 1600 1200 800

V (cm-1 )
100 135
Mass Spectrum UV Spectrum
80 -" \
l
C1l
o, Amax 262 nm (109101> 2.6)
60 C1l
rn
l
.&J Amax 269 nm (109101> 2.6)
40 '0 150

43 M+"= 192 solvent: methanol
20
,II I I I C12H1602
40 80 120 160 200 240 280

m/e
13e NMR Spectrum
DEPT CH 2 CH 3t CHt
I
I I
solvent

I I I
I
I
I
I I I I
I
I I
I II I
200 160 120 80 40 0 s (ppm)
1H NMR Spectrum
expansion
U 7.4 7.2 ppm
-r-r - -
TMS
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
202
Problem 114
1729
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

\
80 ""t1l
'c".
60 '"
l/J
t1l
.0
40 '0 135 M+" =192
0
20
I I I il I ,I I,
40 80 120 160 200 240 280

m/e
I I I I I I I I I I I 1
13C NMR Spectrum
DEPT CH z 1CH 3' CH'

I
I I I I I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
expansion
U ,
8.0 7.5 PPM
I
If
I
-
TMS
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
Problem 115
IR Spectrum 1514
(CHCI3 solution) 1338
4000 3000 2000 1600 1200 800

V (em")
100 M+' = 153 Mass Spectrum UV Spectrum

123
80 ""
III
Ql
a. Amax 227 nm (Io910E 3.9)
60 Ql
U>
40
III
..c
'0
Amax 305 nm (Io910E 4.0)
'if!.

solvent: methanol
20
I IIII II l I C7 H 7N03
40 80 120 160 200 240 280

m/e
__UL...-_
13C NMR Spectrum
solvent
proton decoupled
200 160 120 80 40 0 S (ppm)
L
1H NMR Spectrum
J
,
8.0 7.0 ppm
,..- r-
TMS
- - I
10 9 8 7 6 5 4 3 2 1 o
S (ppm)
204
Problem 116
l-
f- r-r-:
V
- I i
'----
i TMS
8.4 8.2 8.0 ppm
I I
10.5 10 ppm

-
'--
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
205
Problem 117
IR Spectrum
(KBr disc) 1699
4000 3000 2000 1600 1200 800

V (ern")
80 ""l1l
c,
Q) "'max 225 nm (I091QE 4.2)
60 en Q)
"'max 250 nm (I091QE 3.8)
l1l
.c
40 15 104
"'max 293 nm (I0910E 3.2)
<f.
20
1 l M+" 151 < 1% "'max 330 nm (I091QE 2.6)
solvent: methanol
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

134 132 ppm
solvent - .
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
I TMS
I
8.0 ppm
11 10 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
206
Problem 118
IR Spectrum
(liquid film) 1698
4000 3000 2000 1600 1200

V (cm'")

80 "'"
a:>'0." A. max 277 nm (10910 4.2 )
60 a:>
en
'"
.J:J
solvent: methanol
40 a 92 107

20
j I ,I I, l
40 80 120 160 200 240 280
mle
I I I I I I I I I I r
13C NMR Spectrum
I I
DEPT CH 2 1 CH3t CHt
proton decoupled
200
I I
I
160
I I
LJ I
120
I
solvent
80
1
I
I
I
!
40
I I
0
I
8 (ppm)
J_
expansion
1H NMR Spectrum
, , , , , , , ,
7.65 7.45 6.85 6.65 ppm
S JJ TMS
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
207
Problem 119
IR Spectrum
(KBr disc)
1511 1343
4000 3000 2000 1600 1200 800

V (em")
100 M+o147 Mass Spectrum UV Spectrum

101
80
<tl 10910 > 4
Q)
o,
60 Q)
!/l
<tl
..0
40 '0
;ft.
20
I h J .I, CSHSN0 2
40 80 120 160 200 240 280

m/e
1:''"'00
13C NMR Spectrum
(50.0 MHz. CDC'3 solution)
, ,
DEPT CH 2 f CH 3t CHt 85 80 ppm
solvent
f
l
, ,
85 80 ppm
proton decoupled
I I
I I I , , , I I , I , I
200 160 120 80 40 0 s (ppm)

1H NMR Spectrum
(200 MHz. CDC'3 solution)
expansion
I
TMS
---r '------
I i I I
8.25 7.75 ppm
"---"
I I I , , I I I I , I
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
208
Problem 120
IR Spectrum
1766
(KBr disc) 1685
4000 3000 2000 1600 1200 800

V (em")

138
80 ... 43
ttl
Q)
c-
121 Amax 235 nm (10910(; 4.1)
60 Sol
ttl
..c Amax 265 nm (10910(; 3.0 )
40 '0
<fi.
solvent: ethanol
20
J l
40 80 120 160 200 240 280
m/e
I I I I I I I I J I I I
13C NMR Spectrum
DEPT CH2 ' CH 3t CHt
solvent
proton decoupled
I I I
"
-I-
I I I I I i I -I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
expansion
exchanges
---- J J
with 0 20

I
, , , , , ,
11.0 10.0 8.5 8.0 7.5 7.0 ppm
-
TMS
I
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
20 4
Problem 121
3327
1680
IR Spectrum
(nujol mull)
4000 3000 2000 1600 1200 800 0.0

V (crn'")
100 Mass Spectrum

120 0.5
80 ""III
(1)
0-
60 (1)
(/)
M+'
III
.0 165 1.0 UV spectrum
40 '0
92 0.172 mg /10 mls
20 *' 137 path length: 0.5 cm
..I.. ,I, solvent: ethanol
II .I, I C 9H 11 N0 2
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

(20.0 MHz. CDCI3 solution)
l III III
TMS
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum TMS

Ii
-
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
210
Problem 122
3380 3155
IR Spectrum 1646
(KBr disc)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

121
\
80 1d
Q)
Co
60
'"
.c M+"
40 '0 165
20
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
solvent
(100 MHz, CDCI 3/CD 3SOCD3 solution) C-H C-H
solvent
I
H-C-H -CH 3
I
C C
C
I
proton decoupled
I I
I II I
I
I I I I I I I
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
expansion
(400 MHz,CDCI 3/CD 3SOCD3 solution)
exchange
0
with D 20 on warming
1'''''"'
I
8
I I
7
I
ppm
/I l----

vertical expansion
solvent
- -

-
solvent -
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
211
Problem 123
3396
3334
IR Spectrum 1662
(KBr disc)
4000 3000 2000 1600 1200 800

V (ern")

80 "''""
Q)
c.
92
Amax 312 nm (109108 4.3) \
60 Q)
III
M+' 135
40 '0
'"
.n solvent: methanol
<!!-
20
"I.J, ,J.
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

(100 Mz, DMSO-d6 solution)
DEPT CH 2 CH3t CHt
solvent
I
proton decoupled
I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(200 MHz, DMSO-d6 solution)
Exchanges
,--
with 020
r--- r- solvent
residual -,
TMS
- -----J
--'A 1
----'
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
212
Problem 124
IR Spectrum
(KBr disc) 1684
4000 3000 2000 1600 1200 800

V (cm'")

80 :>(.
til
<IJ
C.
106
Amax 246 nm (10910 4.2)
60 <IJ
III
M+" 149
til
.0 Amax 280 nm (10910 3.1)
40 '0 43
*' solvent: methanol
20
I,. 1 Cg H11NO
40 80 120 160 200 240 280

mle
13C NMR Spectrum
L
,
solvent
proton decoupled
I II I
200 160 120 80 40 0 o(ppm)

,
Exchanges
Jl
with 020 on warming
solvent
residual
, , , ,
t , i

7.6 7.4 7.2 ppm
TMS
I I
-f II I I I I I
-
I ,
1
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
213
Problem 125
3284
IR Spectrum
(KBr disc)
1658
4000 3000 2000 1600 1200 800

V (cm'")

108
80
'0."
Q)
Amax 250nm (I0910E 3.1) \
60 Q)
40 '0
''""
.0
M+'
Amax 287 nm (I091OE 2.2)
137
oR. 179
solvent: chloroform
20
J: i j I C lOH13N02
40 80 120 160 200 240 280
mle
13C NMR Spectrum

DEPT CHz 1 CHat CHt
solvent
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
I
7.6 7.0 ppm
exchanges
with 0 20 on warming TMS
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
214
Problem 126
3326
IR Spectrum 1667
(KBrdisc)
4000 3000 2000 1600 1200 800

V (em")

\
80 -'"
Ol
Ql
Co Amax 250 nm (10910E 4.1)
60 Ql
<J)
M+"= 151
Ol
.0 Amax 285 nm (10910E 3.6)
40 '0 43

0
solvent: ethanol
20
Ii l C8H gN0 2
40 80 120 160 200 240 280

m/e
I I I I T T I I I I I I
13C NMR Spectrum
(100.0 MHz. DMSO-d6 solution)
DEPT CH 2 1CH 3t CHt

I
solvent
1
proton decoupled
I
"I
I I I I
I 1 I I I I I I 1 1
200 160 120 80 40 0 s (ppm)
lH NMR Spectrum expansion
Ll
(400 MHz, DMSO-d6 solution)
7.5 7.0 ppm

solvent residual
exchanges
with D 20 on warming
1
TMS
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
215
Problem 127
IR Spectrum
1712
(liquid film)
1277 1254
4000 3000 2000 1600 1200 800

V (ern")

80
\
'"
OJ
o, Amax 257 nm (I091OE 4.3)
60 OJ
<Jl
149
M+"
40 '0
'"
.n

20
en H140 3
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

(50.0 MHz, CDCI 3 solution) - - Resolves into
two signals
at higher field
- - Resolves into
two signals
at higher field
200 160 120 80 40 o a (ppm)

1H NMR Spectrum

I I I I I I I I
4.6 4.2 3.8 ppm 1.6 1.2 ppm
- v----
rr:'
---- TMS
'-J I
10 9 8 7 6 5 4 3 2 1 o
a (ppm)
216
Problem 128
IR Spectrum 1730
(CHCI3 solution)
4000 3000 2000 1600 1200 800

V (ern")

80 ""'c."
l l)
60 ., ll)
UV spectrum
40
'"
.0
"5 M+- 1.0 0.597 mg 110 mls
0 134 194 path length: 0.2 em
20
I, 1. 1 ,.11 l J, I, l I C11H1403
1.5
solvent: ethanol
40 80 120 160 200 240 280 200 250 300 350

m/e A(nm)
13C NMR Spectrum

C-H
C-H H-C-H
I
I
-CH3 I
-CH 3 H-C-H
I
C TMS
200 160 120 80 40 o 8 (ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
217
Problem 129
3295
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

91 0.5 Q)
o
80 ""III co
C1l
UV spectrum \.
a.
Q) -e0
60 Q)
'"
..Q 0.766 mg 110 mls
'" C1l 134 C1l
40 a
..Q
1.0
solvent: methanol
oR.
M+"
20 149 C1QH 1sN
II ,Il ,I, ,1",1 I. u .l,
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)

13C NMR Spectrum
. ,
.
expansion x10
solvent TMS
proton decoupled
11 I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
exchanges
with 0 20
TMS
septet
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
218
Problem 130
IR Spectrum
(liquid film)
1750
4000 3000 2000 1600 1200 800 0.0

V (cm")
100 Mass Spectrum

121 0.5 Gl
g
80 "'" ca
Sl0.
60 s
.c UV spectrum
77 ca
1.0
40 '0 33.9 mg /10 mls
(/!... path length: 0.2 cm
20 M+" solvent: ethanol
180
LI ,ll ,I J I.
40 80 120 160 200 250 300 350

m/e A(nm)
13C NMR Spectrum

(50.0 MHz. CDC/ 3 solution)
Resolves into
two signals at higher field __
Resolves into
two signals at higher field - -
proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
V--
I - ----
.-
TMS
I 1 I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
219
Problem 131
IR Spectrum
(liquid film) 2276
4000 3000 2000 1600 1200 800 0.0

V (em")
9
100 Mass Spectrum

0.5
80 .><
CIl
\.'
Q>
c. 91
60 Q>
Ul M+' UV spectrum
CIl
119
.0
1.0 0.80 mg /10 mls
20 *' Qpath length: 0.1 cm
I C 7H 5NO
1.5
solvent: hexane
40 80 120 160 200 240 280 200 250 300 350

mle A. (nm)
13C NMR Spectrum expansion
(100.0 MH, CDCI, 001'000) .

DEPT
CH 2 + CH3+ CH+ 135
, .
130
i
ppm
,
126
,
125 ppm
.__JlJL 1 expansion
.--
solvent
i , i

I
126 125 ppm
I
I I I I I I I , , I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(400 MHz, CDC'3 solution) expansion
7.4 7.3 7.2 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
220
Problem 132
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

75 \'
80
.,'a-"
-"
Amax 262 nm (109108 2.3)
60 .,
en
'"
.0
solvent: methanol
40 '0
0 91 135 M+ =166 1%)
20
,I I I J, J IJ j C10H1402
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

DEPT 1 CH
CH z 3t CHt
II I I
I
I
proton decoupled
200
I I I
160
I
I 120
I I
solvent
80

I
U I
40
I I
o(ppm)
0
1H NMR Spectrum
expansion
,
5.0 4.5 ppm 3.0 2.5 ppm
.r:
J.
--- F U
TMS
I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
221
Problem 133
IR Spectrum
(CCI 4 solution)
1765
4000 3000 2000 1600 1200 800

V (ern")

80 """
'o," Q)
Amax 269 nm (1091OE 2.7) \,
60 Q)
110
Amax 263 nm
Ul
57
'"
.c (1091O E 2.7)
40 '0 M+" = 222 1%)

20
j Ii I C 12 H140 4
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton coupled
solvent
proton decoupled
I I
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
expansion
J
I i I
',--
I
r--
2.5 2.0 1.5 ppm

r-
- I

----'
TMS
1
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
222
Problem 134
IR Spectrum
(nujol mull)
1720
4000 3000 2000 1600 1200 800 0.0

V (crn'")

0.5 CD
o
80 .><: 149 c:
<lI
CD
o,
o
'"
60 CD en
en .0
<lI <lI UV spectrum
.0 166 1.0
40 '0 194 0.491 mg 110 mls
;fl..
path length: 0.2 cm
20 solvent: ethanol
40 80 120 160 200 250 300 350

m/e A. (nm)
13C NMR Spectrum

- - Resolves into
proton decoupled
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
(100 MHz, CDC1 3 solution)
---- .:

0
f --- TMS
I I 1 I I I
l J
I I I I
1
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
223
Problem 135
IR Spectrum
(liquid film)
1725
4000 3000 2000 1600 1200 800 0.0

V (ern")

0.5 III
o
<:
80
tlI ..
III
Q)
0-
-e0 \
60 Q)
III
III
..c
tlI
UV spectrum
tlI
40 15
..c
1.0 2.010 mg 110 mls
</!
M+' solvent: hexane
20 222
II l JI I II, II II I C 12 H 14 0 4
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
I I I I I I I I I
J l J
13C NMR Spectrum
l
.
C-H
C-H
C
TMS
solvent
proton decoupled
I J
200 160 120 80 40 0 s (ppm)

1H NMR Spectrum
J

TMS
I I I
I I I I I I I
10 9 8 7 6 5 4 3 2 1 0'"
o(ppm)
224
Problem 136
IR Spectrum
(liquid film) 1724
4000 3000 2000 1600 1200 800

V (cm")

80
'"
CI)
Q.
149
60 CI)
40 15
'"'"
.Q
M+"
222
20
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

I I
135 130 ppm
I
./ 135
I
130 ppm
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
--'
i , i
i
8.6 8.2 7.8 7.4 ppm
--
I
--r-
I I
I I I I I I I
TMS
I
I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
225
Problem 137
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

80 -"
<0
Q)
c. Amax 220 nm (109
101':
3.7) \
60 Q)
'"
<0
.0 Amax 274 nm (109101': 3.3)
40 '0 166
20 * solvent: ethanol
I I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
I I I
. proton decoupled
I I
200
I I
160
I
Ll I
120
I
solvent
80
I
,
I
,
40
I
I I
l 0
I
o(ppm)
1H NMR Spectrum
expansion expansion
expansion
J_
ul
7.3
i i
7.0 ppm
2.5 2.4 ppm 1.2 1.1 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
226
Problem 138
IR Spectrum
(liquid film) 1730
4000 3000 2000 1600 1200 800

V (cm'")

163
\'
80 -"
I1l
Ql
c. 1
Amax 223 nm (Io91Ql'.: 3.9)

60 Ql
en
I1l
.Q Amax 275 nm (Io9 10l'.: 3.1 )
40 '0
20
;j?
104
Amax 281 nm (I0910l'.: 3.0 )
135
II C10H1004
solvent r- ethanol
40 80 120 160 200 240 280

m/e
I I I I I I -I I I I I T
13C NMR Spectrum
DEPT CH2 + CH3+ CH+

I
I
r
solvent
proton decoupled +
I I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
(400 MHz. CDCI 3 solution) expansion
il
7.6 7.4 ppm
TMS
- 1 -
I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)

Problem 139
IR Spectrum
(liquid film) 1702
4000 3000 2000 1600 1200 800

V (ern")
80 .><
III
III
a.
60 III No significant UV
<II
III
.c 42
M+"= 112
40 '0
a"-
20
I C7H12O
l'L
40 80 120 160 200 240 280
m/e
I I I I I I I , I I I I
13C NMR Spectrum
LlJ
solvent
proton.decoupled
I
I I I I I I I I I , I I
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
2.5 2.4 ppm 1.7 1.6 ppm
TMS
-
I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
228
Problem 140
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

91
\.
80
I1l
Q)
c,
60 Q)
'"
I1l
..c M+"= 92 solvent: ethanol
40 '0

20
J C 7Ha
40 80 120 160 200 240 280

m/e
I I I I I I I I I I , 1
13e NMR Spectrum
(100.0 MHz, CDCI J solution)
DEPT CH2 , CH J+ CH+

I
proton decoupled ,
solvent
I
200 160 120 80 40 0 (5 (ppm)
1H NMR Spectrum
expansion
expansion expansion
expansion
Jl L
I--
,
j TMS
i
6.5 ppm 6.1 ppm 5.3 5.2 ppm 2.2 2.1 ppm
6.6 6.2
- - - I
10 9 8 7 6 5 4 3 2 1 0
(5 (ppm)
229
Problem 141
IR Spectrum
1694
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
80 "'"
CIl 69 \,'
Ql
c-
VI
CIl
40 0
20 *' M+' = 84
It. ,I
40 80 120 160 200 240 280

mle
I I I I I I I I I T I I
13C NMR Spectrum
proton decoupled
200
I I I
160
I I
120
I
solvent
80
I I I
40
ul I
0
I
o(ppm)
1H NMR Spectrum
expansion
expansion

2.1 2.0 1.9 ppm 2.0 1.5 1.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
230
Problem 142
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (cm'")

\;
80 "'c,"
III
85
oil
60 oil No significant UV
'"
III
40 '0
cf!..,
20
40 80 120 160 200 240 280

m/e
13e NMR Spectrum

,
l
solvent
proton
I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
JL
Exchanges
with D20
A i
12.0 11.5 ppm 1.7 1.5 ppm 1.1 0.9 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
231
'U-
Problem 143
IR Spectrum 1668
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
105
100 Mass Spectrum
80 \,.
'0-I"II
60 III
en 77
'"
.c
40 '0 M+"= 146
of'. 69
20
l, C10H10O
I' J I "
40 80 120 160 200 240 280

m/e
I I I I I I , I I , I I
13C NMR Spectrum
DEPT CH 2 CH 3t CHt
I I
I
proton decoupled
200
I
I I I
160
I
I J I
120
I
solvent
80
I
I
I I
40
I
Ll 0
I
o(ppm)
lH NMR Spectrum
(4 00 MHz, CDCI 3 solution)

expansion expansion

expansion
I-- l.- I,.....
U ,
8 .0
, ,
7.5 ppm
,
,
2.6
,
2.5 ppm
---'
,
1.2
i
1.0
'------
ppm
, Ir-
- - - - I-
TM
I
s
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
232
Problem 144
JR Spectrum
(liquid film)
1734
4000 3000 2000 1600 800

V (ern")
100 Mass Spectrum
80 .x.
etl
Q)
o,
III
etl
.J:J absorption above 220 nm
40 '0
;f!.
55 83
20 I 100
,l ,I 113
40 80 120 160 200 240 280

mle
I I I , I I I I I I I
13C NMR Spectrum
i I
I I
I
" solvent
proton decoupled
I I I
I
I I I I I
I
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
expansions
1 lAll . 1.1. ppm

1.2
TMS
10 9 8 7 6 5 4 3 2 1 0
I

o(ppm)

1\
,.

23:
IMl iII j ..." _ . '
Problem 145
IR Spectrum 1728
(KBr disc)
4000 3000 2000 1600 1200 800

V (ern")
80 "'" 98
'"
Q)
0-
No significant UV
60 Q)
40
'"'"
.J::J
'0
;;R.
20
1.1 I,ll ..11.1
40 80 120 160 200 240 280

m/e
I I I I I I f I I I ,
13e NMR Spectrum
,

,
DEPT CH2 t CH 3t CHt
I 28 27 ppm

lLJ .
solvent
proton decoupled
t 28
i i

27 ppm
I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
expansion
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
234
Problem 146
IR Spectrum
(liquid film) 1654
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

30
43
80 -'"
III
Q)
Q.
.a'"
III
40 '0
;fl.
20
III
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

DEPT CH 2 t CH 3t CHt
,I
solvent
proton decoupled
I I I I I I I I
I
I I
lJ I I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
expansion
(200 MHz, CDCI 3 solution) with irradiation (decoupling)
at 15 7.4 ppm
'---
!
3.0
I
M
expansion
I
2.5
L I
2.0 ppm
r-

t-
exchanges
with 0 20 on warming
Y- -- ---'
TMS
l I
t 10 9 8 7 6 5 4 3 2 1 0
h

o(ppm)
fi
235
5k
Problem 14i
3283
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
80 .>< \ ..
'"
Q)
0-
No significant UV
60 Ql
<Il
co
.n absorption above 220 nm
40 '0

20
M+"= 88 1%)
C4H12N 2
40 80 120 160 200 240 280

m/e
I I I I I I I I I I T T
13C NMR Spectrum
n
..
proton decoupled
,
solvent
I
200 160 120 80 40 0 () (ppm)
1H NMR Spectrum

r Exchanges
with 020
l--
. . . .
2,0 1.8 ppm
. . . .
0.8 0.6 ppm
TMS
........ -1'---t
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
236
Problem 148
3284
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")

t-
80 .><
'a."
Q)
Vl
'"
40 '0 56
20 *" M+"= 102 1%)

.U 1 J
CSH14N 2
40 80 120 160 200 240 280

mle
,.. , ". .-.. . . fTl'' '

I I I I I I I I I I T
13C NMR Spectrum
(100.0 MHz, COCI 3 solution) lIIWoo""""'' ' ' ' ' ' ' _'-' ''''''''_ ; i'
proton decoupled
solvent
,
I I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
(400 MHz, COC1 3 solution)
Exchanges
expansions
with 02
2.2 2.1 2.0 ppm 0.9 0.8 ppm

TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
237
Problem 149
IRSpectrum
(liquid film)
1718
4000 3000 2000 1600 1200 800 0.0

V (em")

0.5
s
80 ""...
III
...c

\,.
c- o
60 Ul UV spectrum
III
...
Ul
91 M+" ...
J:J
0.466 mg 110 mls

40
J:J
'0 212 1.0
77 a path length: 0.2 cm

!2 path length: 2.0cm
20
II ,I ,1"1. I I,
C14H1202
1.5
solvent: ethanol
40 80 120 160 200 240 280 200 250 300 350

m/e A(nm)
I I I I I I I I I I
13 C NMR spectr=-u Resolves into two signals at higher field
(50.0 MHz, CDCI 3
solution)

I
134 ppm I
DEPT CH 3t CHt - - - - - -......... "----------r---------

, I III J Resolves into two signals
at higher field
,3. 130 PO"; II

I
proton decoupled
I I
1
I I

I I
solvent
I
'--I I I
_ I
200 160. 80 40
1H NMR Spectrum
TMS
- -
_ _ _ _- - - - J L-J \."-- J ...._ - - - " - J\-.
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
238
Problem 150
IR Spectrum
(CHCI 3 solution) 1700
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

105
80
l'll
Q)
a.
60 .,
Q)
l'll UV spectrum
J:l M+" 1.0
40 '0
lI
77 226 0.806 mg 110 mls
path length: 0.2 cm
20 91 solvent: ethanol
1,1 J .I II C15H1402
1.5
40 80 120 160 200 240 280 200 250 300 350
mle A. (nm)
13C NMR Spectrum

off-resonance decoupled TMS
proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
239
Problem 151
IR Spectrum
(CHCI 3 solution) 1762
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

91 118 0.5 III
o
c:
80 .:.t.
<ll <ll \.
III
0-

0
60 III
(I)
(I)
.0
<ll
<ll
.0
1.0 UV spectrum
40 '0 108
;;R. 3.141 mg 110 mls
1
M+'
20 226 path length: 1.00 cm
IL .I . 1.. solvent: hexane

1.
C15H1402 1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum

TMS
solvent
proton decoupled
200 160 120 80 40 o 3 (ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
3 (ppm)
240
Problem 152
IR Spectrum
(liquid film)
4000 3000 2000 1S00 1200 800

V (cm'")

\ ..
80 -'"
to
Q)
C.
SO Q)
'"
to
.0 242
M+" = 310-322 1%)
40 '0
170
20
C aH 4CI s
40 80 120 1S0 200 240 280

m/e
13C NMR Spectrum
j
solvent
proton decoupled
I 11 I I
200 160 120 80 40 0 3 (ppm)
1H NMR Spectrum
J
expansion
I--
'---
- 8.5
I I
8.0 ppm
'-----' '----'
10 9 8 7 6 5 4 3 2 1 o
3 (ppm)
241
Problem 153
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200

V (ern")

f-
80 "'.,<ll"
.,
0- Amax 246 nm (109101': 3.7) "
60
'"<ll
.c Amax 273 nm (109101': 2.6)
40 '0
*- solvent: ethanol
20
J I
40 80 120 160 200 240 280

m/e
I I I I I I , I I I I I
13C NMR Spectrum
(100.0 MHz, CDCI3 solution, 360 K)
DEPT CH 2 CH 3 + CH +
I I
r
-L
,
138.5
,
138.0 PPM
I
solvent
proton decoupled
I I I
I I I I I
I
I
I I I I
200 160 120 80 40 0 o(ppm)
1-
1H NMR Spectrum at 360 K
r,
, , ,
3.4 3.5 ppm 1.2 1.1 ppm
3.0 1.0
at 298 K
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
242
Problem 154
exchanges
with 0 2 0
I
7.5 ppm
10 9 8 7 6 5 4' 3 2 1 o
o(ppm)
243
Problem 155
IR Spectrum 1770 1700

(CHCI3 solution)
4000 3000 2000 1600 1200 800 0.0

V (ern")

43
0.5
80 .,,;
\c
'a."
Q)
138
60 Q)
rJl UV spectrum
..0 '" 1.0 0.458 mg /10 mls
40 a a path length: 1.00 cm
<f!.
I M+" !l path length: 0.2 cm
20 180 solvent: methanol
III, .III III CgH a0 4
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

DEPT CH 2 t CH 3t CHt
U I .
solvent
I I I I
175 170 165 ppm
proton decoupled
I I I I
I I
II I I I I I I
200 160 120 80 40 o 0 (ppm)

(200 MHz, CDCI 3 solution) with resolution enhancement
broad resonance
exchanges
with 0 20
8.2 7.8 7.4 ppm

TMS
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
244
Problem 156
IR Spectrum
(CHCI3 solution)
4000 3000 2000 1600 1200 800 0.0

V (cm'")
100 Mass Spectrum

0.5 Q)
o
80 ..l< c
<lI <lI
Q)
0-
-e0
60 Q)
(/) 90
(/)
..Q
<lI
UV spectrum
<lI M+'
40
..Q
'0
1.0 0.245 mg 110 mls
249/251/253
20 *" 91
solvent: ethanol
II" J .. j,j
C 6H SNBr2
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

1
,i
TMS
I
solvent
proton decoupled
I
I
i
I I
200
I I
160
I
I I
120
I I
80
III
I
40
I I I
0 o(ppm)
f
t lH NMR Spectrum
(100 MHz, COCI 3 solution) TMS
exchanges
with 0 20
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
245
Problem 157
IR Spectrum
(KBrdisc)
4000 3000 2000 1600 1200 800 0.0

V (cm'")

0.5 CD
57 g
80 "''C""D
0.
.e
60 CD ..c UV spectrum
''""
..c
M+' 1.0 '" 1.208mg 110 mls
<;e
solvent: ethanol
20
111 'oJ II ,I .1 I ,C 14H 22O
1.5 L.J..- .................
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13e NMR Spectrum

TMS
proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(100 MHz. COCI3 solution)
expansion
I I
25 Hz
If-
exchanges
TMS
r with 0 20
---'
A A j
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
246
Problem 158
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
100 261/263/265 Mass Spectrum

182/184
80 7;i
Q)
a-
60 5l
1l 197/199 M+'
40 '0 276/278/280
20
40 80 120 160 200 240 280

m/e
I I I I I I J I I I I I
13C NMR Spectrum
I I
I
/
l solvent
I
I
proton decoupled
I BI
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
7.5
expansion
I
7.0 ppm
_J I
3.0
expansions
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
24'
i.
Problem 159
1689
IR Spectrum
(KBrdisc)
4000 3000 2000 1600 1200 800

V (ern")

227/229
80 -""
'a."
Q)
M+"
60 Q)
en 242/244
'"
.0 163
40 (;
*-
20
40 80 120 160 200 240 280

m/e
13C NMR Spectrum one signal even at high field

_ _tiJ_-----'J_ Resolves into


solvent
proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(200 MH,. CDCI, 001"",,0)
1 II I
expansions
exchanges
with DzO I I I I
8.2 8.0 7.8 7.6 ppm
I I I
1.4 1.3 1.2 ppm
I
11.0 10.0 TMS
3.1 3.0 2.9 ppm
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
248
Problem 160
IR Spectrum
4000 3000 2000 1600 1200 800 0.0

V (crn'")

0.5 eo
c:
80 .><
'"
4l
c-
-e'o"
60 4l
(/)
(/)
..0 UV spectrum
'"
..0 M+' 1.0 '" 0.298 mg 110 mls
40 '0 150
path length: 0.5 cm
0
20
Iii JI I. T Ca H 603
1.5
solvent: ethanol
40 80 120 160 200 240 280 200 250 300 350

m/e A. (nm)
13C NMR Spectrum

(20.0 MHz, CDC13 solution) solvent
,
solvent TMS
proton decoupled
I I I III 1
200 160 120 80 40 0 o(ppm)
TMS
1H NMR Spectrum
J --
expansion
7.70 ppm 6.80 ppm
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
249
Problem 161
IR Spectrum 1526 1353

(liquid film)
4000 3000 2000 1600 1200 800

V (cm'")
80 -'" 134
CIl \i
<D
Co
60 <D
VJ
CIl
.0
40 a M+'
*' 151
20
1 . ,J. J I CaH gN02
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
__Ul"""-----_l
DEPT CH2 , CH 3+ CH+
I I
.proton decoupled solvent
I III
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
- Resolves into two signals
of equal intensity
et higher field
expansion
____I
I
7.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
250
Problem 162
1
i IR Spectrum
(KBr disc)
I 4000 3000 2000 1600

V (cm'")
1200 800
r 100 159 Mass Spectrum

I \r
80 .><
r '"c,
Q>
I 60 Q>
M+'
'"
'"
.0
194/196
40 '0
>!i!.
0"
I
20
40 80 120 160 200 240 280

t m/e
13C NMR Spectrum

expansion
LL
135 ppm
Resolves into

I I
expansion 135 130 ppm
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
251
Problem 163
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (cm'")
100 Mass Spectrum
80 -""
11l M+"
Ql
c. 195-201
60 Ql
(J)
11l
.0
40 '0
;f!.
20
C S H 4CI3N
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
U
DEPT CH 2 CH 3t
-
CHt
solvent
;' proton decoupled

I jI I
200 160 120 80 40 0 () (ppm)
1H NMR Spectrum
exchanges
with 0 20

r---
l-----"
TMS
1
""
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
252
Problem 164
.(
.
IR Spectrum
(CHCI3 solution)

4000 3000 2000 1600 1200 800 '-
V (crn'")
,.- --,0.0 -'
100 Mass Spectrum 0.5

80 .><:
sc \r

I- 0-
M+" '"en UV spectrum
60 390 .c
'"
.c 248 1.0 '" 0.390 mg I 10 mls
40 "5 path length: 1.00 cm
o . 233
solvent: dioxan
20 375
I.
.-
40 80 120 160 200 240 280 320 360 400
250 300 350
m/e A. (nm)
13c NMR Spectrum solvent

(20.0 MHz, CD 3SOCD 3 solution)
C-H
C C-H
C
proton decoupled TMS
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
6H
TMS
residual CHCI 3
lH in solvent
lH
I 1
I I I I I I I I l l I
I
I 8 7 0
10 9 6 5 4 3 2 1
I s (ppm)
t
!
253
f
Problem 165
IR Spectrum
(liquid film) 1685
4000 3000 2000 1600 1200 800

V (ern")
100t- 68 Mass Spectrum UV Spectrum

80 t-.><<'ll '\ \!
CIl
0-
/\,max 225nm (I0910E 3.9)
60 CIl
Ul
'"
.0
M+"= 96 solvent: methanol
40 '0
*-
20
,J'
""I " " " ' , "
l CSHSO
40 80 120 160 200 240 2S0

m/e
13C NMR Spectrum

I
200 160 120 80 40 o a(ppm)

1H NMR Spectrum
(400 MHz. CDCI3 solution)
, , , ,
6.9 2.4 2.2 ppm 1.9 1.8 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
a (ppm)
254
I '..
Problem 166
3457
IR Spectrum 1671
(CHC'3 solution)
4000 3000 2000 1600 1200 800

V (cm'")

\j
80 .><
'"
Ql
C>- Amax 263 nm (109101:: 3.9)
60 Ql
<Il
'"
J:l Amax 305 nm (109101:: 2.1 )
40 '0
<f!.
solvent: hexane
20
III ,I I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

40 30 20 ppm

.I
I I solvent l
200 160 120 80 40 o 0 (ppm)

(400 MHz. CDC'3 solution)
expansion
Exchanges 2.5 2.0 ppm

withD20 t
i o o
6.4 6.2 PPM
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
255
Problem 167
IR Spectrum
(liquid film) 1666
4000 3000 2000 1600 1200 800

V (ern")

80 """- 81
ttl
<lJ
C.
Amax 234 nm (109108 4.1)
60 <lJ
III
ttl
.c 43 solvent: ethanol
40 '0 M+"= 124

20
I I ,I CaH 120
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

25 20 ppm
25 20 ppm
proton decoupled
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
(400 MHz, CDCI3 solution) /"'oJ
.1
I
A 6.80 6.75 ppm 2.2

, ,
2.0 ppm
,
1.5
,
1.4 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
256
Problem 168
.(.
\;
UV spectrum
10.8 mg 1100 mls

path length: 0.1 cm
250 300 350

A (nm)
13C NMR Spectrum

DEPT CH2 , CH3t CHt
,
solvent
W
proton decoupled
I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
(400 MHz, CDCI 3 solution) with irradiation
at 05.95
---- '--
expansion
r-
A
-11-2.55 Hz -11- 2.75 Hz
!;'

!
TMS
expansion

I I I I I I I J I
6.0 5.9 ppm S 2.0 1.9 1.8 ppm
- -
A
i
,,;
1,.
I
10 9 8 7 6
I
5
I
4 3 2 1 o
o(ppm)
v.
257
Problem 169
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
80 "'ill" \)
III
0. M+"= 118
Amax 260 nm (109101': 2.9)
60 ill
Ul
III
.0 Amax 266 nm (109101': 3.1)
40 '0
20 *' Amax 272 nm (109101': 3.1 )

I d .1. C g H 1Q
solvent: methanol
40 80 120 160 200 240 280

m/e
I I I I I , I I I I I I
13C NMR Spectrum


1
,i
I
proton decoupled
200
I
160
I I

120
I I
solvent
80
1
I
I I
40
U I
0
I
o(ppm)
:..,.
1H NMR Spectrum
expansion <
expansion
expansion
j
7.4 7.3 ppm 3.2 3.0 ppm
2.3 2.2 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
258
Problem 170
IR Spectrum
(liquid film) 1708
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

0.5 II>
o \i
80 .>< 145 C
'"
Ql
0-
M+'
160
-e0'"
60 Ql
U)
U)
J:J UV spectrum
'"
J:J
1.0 '" 0.364 mg 110 mls
40 '0
path length: 0.5 cm
20 solvent: cyclohexane
I. ,I J, ,I .,1 U C 11 H120
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

, f i
135 130 125 ppm
i i i
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
exchanges after
prolonged treatment
,
with 0 20 containing
a trace of DCI or NaOD
It---
--
TMS
----'
j
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
259
Problem 171
IR Spectrum 1719
(CCI4 Solution)
4000 3000 2000 1600 1200 800

V (ern")
100 104 M+" = 132 Mass Spectrum UV Spectrum

80 x
III
Q)
0.
Amax =243nm (109108 4.1)\1
60 Q)
<Jl
III
.0 Amax = 291 nm (109108 3.4)
40 '0
;f!. solvent: ethanol
20
II I C9HaO
40 80 120 160 200 240 280

m/e
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
260
Problem 172
IR Spectrum 1751
(CHCI3 solution)
4000 3000 2000 1600 1200 SOO

V (ern")

104
SO "'CIl"
Q)
e- Amax 26S nm (109101'; 3.1)
60 Q)
til
CIl
.&J Amax 275 nm (109101'; 3.1)
40 '0 M+"=132
;ft

solvent: ethanol
20
II I l CgHSO
40 SO 120 160 200 240 2S0

m/e
13C NMR Spectrum
proton decoupled
I I
200
I
160
I I
J I
120
I
solvent
80
I
I
I I
40
I
o
I
0 (ppm)
1H NMR Spectrum
TMS
I
I I I I I I
I I I I I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
26:
Problem 173
1683
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

80 M+"= 146
"'Cl>"
III
Amax 249 nm (log 10 '" 4.1) IV
0.
60 Cl>
l/)
40
III
.0
a
Amax 292 nm (log10'" 3.3)

solvent: ethanol
20
40 80 120 160 200 240 280

m/e
I I I I , I I I I
13C NMR Spectrum

DEPT CH 3t CHt

ill
ppm 130
i
125
,
I II
proton d.","P''''
I
J
ill uJ I
ppm 130
.
I
,
125 I ..
solvent
200 160 120 80 40 0 8 (ppm)
1H NMR Spectrum
expansion
, i
8.0 7.5 ppm 2.5 2.0 ppm

TMS
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
262
Problem 174
IR Spectrum
(liquid film) 1716
4000 3000 2000 1600 1200 800

V (crn'")

\i
80 .><
'0.C"Il Amax 265 nm (1091OE 3.0)
60 CIl
III M+'= 146
'"
.0 Amax 272 nm (l091OE 3.1)
40 '0

20 Amax 294 nm (l091OE 1.9)

I J I j, II ,1 II I C1QH1QO
solvent: ethanol
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
129 128 ppm

expansion I

proton decoupled
.-J
I
200
I I
160
I I
II 120
I
129
I
128 ppm
80
I
solvent
,---J
I
UJ
40
I I
0
I
o(ppm)
1H NMR Spectrum
expansion
expansion
{ JL
l
7.3
I I
7.2
I
ppm
-

3.2
I I
3.0
I
ppm
-

---"
..--

---
I
2.6
I
2.5
I
ppm
TMS
I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
263
Problem 175
IR Spectrum
(CHCI3 solution)
4000 3000 2000 1600 1200 800 0.0

V (crn'")

0.5 CD
u
c
80 .;,<
M+" '"
'0."
CD lBO
0
60 CD
III
III
.c
40
.c'"
'0
1.0 '" UV spectrum
;ft 0.194 mg 110 mls
'JJ,
C 14 H12 solvent: cyclohexane
1.5
40 80 120 160 200 240 280 200 250 300 350
mle A. (nm)
13C NMR Spectrum

solvent
_____'-----'----'w'-__--'---
proton decoupled
_
200 160 120 80 40 o 0 (ppm)
TMS
lH NMR Spectrum
>--
-.!
)1

U 1 I
'-
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
264
Problem 176
IR Spectrum 1715
(KBr disc)
4000 3000 2000 1600 1200 800

V (ern")

\i
80 r-><co
Ql
a. M+"= 180 Amax 265 nm (109108 4.5)
60 Ql
en
co
.c 152 Amax 330 nm (109108 4.2)
40 '0
<f!.
solvent: ethanol
20
I .I C13H 8O
40 80 120 160 200 240 280

mle
13e NMR Spectrum expansion

(100.0 MHz, CDCI 3
i i i
DEPT
CH 1 CH CHt
135 125 ppm
-"-..I-J....I... _
2 3t
proton decoupled
UII
i
135
i
125 ppm
I
I
solvent
1
200 160 120 80 40 o 0 (ppm)
expansion
1H NMR Spectrum
M
(400 MHz, CDaCN solution)
I,' "
7.65 7.60 7.55 ppm 7.35 7.30 ppm
solvent
residual H 2 0 in solvent - residual TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
26:
Problem 177
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (cm'")

43
80 x
co 29 \i
Q)
Co
60 Q)
sn
No significant UV
co
.i:J
40 '0

M+" = 132 1%)
89
20
.. 87 1 117 131 C SH 120 3
1 I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
III
solvent TMS
proton decoupled
III I
I .
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
J TMS
1
I I I I I I I I I I ;
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
266
Problem 178
13C NMR Spectrum

I
H-C-H
I
C TMS
C
solvent
proton decoupled
ill
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
267
Problem 179
1800
IR Spectrum
(KBr disc) 1765
4000 3000 2000 1600 1200 800

V (ern")
80
<II 70
<Il
60
C.
<Il
l/l
No significant uv
<II
40 '0
;/!.
20
1
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

solvent
proton decoupled
I I
I I
I I I I I I
200 160 120 80 40 0 s (ppm)
lH NMR Spectrum
L ,
2.8
i
2.7 ppm
,
1.9 1.8
,
ppm
,.- r-
I I I I I I I
-
I
---J
I
-
I
TMS
I
I
10 9 8 7 6 5 4 3 2 1 0
s (ppm)
268
Problem 180
3405 1721
4000 3000 2000 1600 1200 800

V (ern")
1001- 43 Mass Spectrum

\/
80 oX
'"c.
Q>
60 Q>
'"
I- .0
'" absorption above 220 nm
40 '0
:>e
0 ..
20 M+"=1301%)
I, 1..11 IJ. ,I

C6H 1003
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
I
DEPT CH 2 f CH 3t CHt
solvent
proton decoupled f
1
I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansions
Exchanges
, , , with 020
4.4 4.2 ppm 2.5 1.8 1.6 ppm
f
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
269
Problem 181
3207
IR Spectrum
(KBrdisc) 1678
4000 3000 2000 1600 1200 800

V (cm'")
80 "'"
'a.C"Il Amax 230 nm (10910 3.6) pH Y1
60 CIl lJl
'"
.0
Amax 230 nm (10910 4.4) pH 13
40 '0
<f!. M+"= 155 solvent: water
20
40 80 120 160 200 240 280

m/e
I I I I I I I I I T
13C NMR Spectrum

35 34 ppm I
expansion
I
L
proton decoupled
I I
200
I I
160
I
120
solvent
I I
35
I
I
80
34
I
ppm
llu
I
40
I
0
I
o(ppm)
1H NMR Spectrum
expansion
2.6 2.4 ppm 2.5 2.0 1.5 ppm

Exchanges
TMS
with 020
10 9 8 7 6 5 4 3 2 - 1 0
s (ppm)
270
Problem 182
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

I-
80 .><
<ll
4l 56
a.
l/l
<ll
40 (;
42

D
20 M+"= 155
I, I I I C10H 21N
40 80 120 160 200 240 280

m/e
I I I I I I I I I I T T
13C NMR Spectrum
I
DEPT CH 2 , CHJt CHt 1
proton decoupled ,
solvent
I I I I
200 160 120 80 40 o 0 {ppm}
1H NMR Spectrum
expansion
J TMS
10 9 8 7 6 5 4 3 2 1 o
o{ppm}
271
Problem 183
IR Spectrum
(KBr disc)
3249
4000 3000 2000 1600 1200 800

V (cm'")
80 -"
'0-<"1l
60 <1l
UJ
'"
.0
40 '0
*" 127
M+" = 142 1%)
20
,I I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

solvent
proton decoupled

200 160 120 80 40 o a (ppm)
1H NMR Spectrum
Exchanges
with 020
-
-- ........
TMS
I
10 9 8 7 6 5 4 3 2 1 0
a (ppm)
272
Problem 184
IR Spectrum 1682
(liquid film)
4000 3000 2000 1600 1200 800

V (em")

!Ii
80 .,'"
-""
I0910c > 4.0
60 .,
Co
40
''""
.c
'0
<f!.
M+
94

20
jl .II Il C 6H6O
40 80 120 160 200 240 280

mle
13C NMR Spectrum

I
Lr.
DEPT CHz' CHJ CH+
,'01'" d=",,:J
I I
200
I I
160
J
I I
120
4
I I
80
solvent
I I
40
j"
I I
0 o(ppm)
1H NMR Spectrum
v-----
I---
1- S- -
----J
TMS
a , 1
I I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
273
Problem 185
2100
IR Spectrum
3275 (liquid film) 1630
4000 3000 2000 1600 1200 800 0.0

V (crn'")
100 Mass Spectrum

0.5
80
CD
c. UV spectrum
60 3l
III 0.182 mg 110 mls
.Q
1.0 path length: 0.5 cm
40 '0
*- solvent: dioxan
20
I, ..I
1.5 "'"""-'--'- ........
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

expansion
I I
80 70 ppm
I i
80 70 ppm
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
expansions with
20 Hz
I I I I
6.4 4.45 3.1 3.0 ppm
I I I I
-r I I I
J
I
I I I
TMS
I
I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
274
Problem 186
2240
3370
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (crn'")
100 Mass Spectrum

0.5 8
43 c:
80 102
Q)
0.
'"

UV spectrum
60 .0
'"
.0
156 M+' = 174 1%) 1.0 '" 0.434 mg 110 mls
40 '0 path length: 0.2 cm
o "
solvent: methanol
20
C 12 H 14 0
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum

(20.0MHz, COC'3 solution)
C-H 2 xC-H
- - Resolves into
I
H-C-H
I -CH
solvent 3
-CH
3
C
C
C
C 1 TMS
proton decoupled
I I l III l
200 160 120 80 40 0 o(ppm)
lH NMR Spectrum TMS


lH
exchanges
with 0 20 -
------- ----- ....._ _- - J
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
275
Problem 187
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (cm'")

M+-
80 x 140
'"
<Il
0-
109 10 1': > 4.0
60 <Il
III
'"
.0
40 '15
cf'.
20
,j 1 {1.l1 ,1111
j C 11 Ha
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

two resolved signals
--- at higher field
expansion
two resolved signals

--- at higher field I solvent
I
70 ppm
proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
\ I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
276
Problem 188
3332
3267
IR Spectrum 1713
(KBr disc)
4000 3000 2000 1600 1200 800

V (crn'")

\i
80
Q) 109101> > 4.0
c-
60 :g
40 '0
'"
J:J
140

20
l
40 80 120 160 200 240 280
role
I I I I I I I. I I I I I
13C NMR Spectrum
DEPT CHzt CH 3t CHt
U solvent
proton decoupled
I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
Exchanges
with 020
I-

j "
---' -..J'
TMS
10 9 8 7 6 5 4 3 2 1 0
o (ppm)
277
If
I
Problem 189
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
100 121/123 Mass Spectrum
80 .x:
III
Q)
Co
41
No significant UV
"
60 Q)
Ul
III
40 '0
M+" 200/202/204
20
I II ,I, C 3H S Br2
40 80 120 160 200 240 280

m/e
I I I I I I I I I T
13C NMR Spectrum

_ _
proton decoupled
solvent
40 o 0 (ppm)
200 160 120 80
1H NMR Spectrum
(400 MHz, CDCI3 solution) expansion
expansion
expansion
"'I' "" 'I 1'

1.9 1.8 ppm
TMS
""1""""'1" "'" I' ""'" 'I ' " I"
4.3 4.2 ppm 3.8 3.6 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
278
Problem 190
IR Spectrum
3433 1713
(KBrdisc)
4000 3000 2000 1600 1200 800

V (ern")
80 58
1'0
CD
Co
60 CD 74 No significant UV
en
1'0
40 15
cf!..
20 I-
I III
40 80 120 160 200 240 280

m/e
I I I I I I I I I I T I
13C NMR Spectrum
solvent
proton decoupled
L
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum expansions

4.2 4.1 ppm 2.2 2.1 ppm 1.0 0.9 ppm
Note: very broad signal from

about 8 ppm to 5.5 ppm
exchanges with 0 20
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
279
Problem 191
IR Spectrum
3350 (liquid film)
4000 3000 2000 1600 1200 aoo

V (ern")
1001- Mass Spectrum

61
ao .:>< 43 \I
'a."
(I)
No significant UV
60 (I)
V>
'"
..0 absorption above 220 nm
40 '0
*'
20
M+o= 92 1%)
C3Ha0 3
40 ao 120 160 200 240 2aO

m/e
13C NMR Spectrum
(100.0 MHz. 020 solution)
I
proton decoupled
I I I I I I I
200 160 120 80 40 o 3 (ppm)
1H NMR Spectrum
(400 MHz. 020 solution)
H20 and HOO
in solvent
expansion
ppm
10 9 8 7 6 5 4 3 2 1 o
3 (ppm)
280
Problem 192
3305 IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (cm'")

80 .x
<lI
<Il
C.
60 <Il
CI)
No significant UV
<lI 59
..c
40 '0
:;,'!.
o.
M+" = 74 (< 1%)
20
I, JJ LI
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton coupled
.u_Uuk
proton decoupled
200 160 120

solvent m
80

40
lU 0 () (ppm)
1H NMR Spectrum
exchanges
with D20
expansion
3.5 2.5 1.5 ppm
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
281
Problem 193
IR Spectrum
1033
(KBr disc)
4000 3000 2000 1600 1200 800

V (crn'")
80 .x:
til
III
o,
60 III
VI
til
.0
40 '0
*-
20 123
I I
40 80 120 160 200 240 280

mle
J I I J I I I I I T J
NMR Spectrum
_L
13C expansion
(100.0 MH>, CDCI,

DEPT ,
CH2 t CHJ CHt 130 129 ppm
I
proton, decoupled
note
lJl
'" 130
,
129 ppm
solvent
t
I
200 160 120 80 40 0 () (ppm)
1H NMR Spectrum
expansion

4,0 3.85 ppm TMS
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
282
Problem 194
r
IR Spectrum
(CHCI3 solution) 1675 1580
4000 3000 2000 1600 1200 800 0.0

V (cm'")

135 B
c:
80 -'"
'Co"
Ql M+' '"

0
60 Ql 180 III
III .0
ro UVspectrum
'"
.0
1.0
40 '0 0.390 mg 110 mls
*" path length: 0.2 cm
20 solvent: ethanol
CgH aS0 2
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

(20.0 MHz, CDC'3 SOIUlIon)j iI
off-resonance decoupled JL expansion
solvent
TMS
I
130 ppm
proton decoupled
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
TMS

with O2
Ir-
i

10.9
I
,----J
-
\.l
I I
, I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
283
Problem 195
IR Spectrum 1350
4000 3000 2000 1600 1200 800 0.0

V (ern")

0.5
B
c
80 .><
'"
al M+' e'"
60
c,
al
155
200 s
.D
III
'" '" - UV spectrum

.D
1.0
40 '0
172 7.260 mg 110 mls
*'
II.
J u l I CgH 120 3S solvent: ethanol
1.5 ............................................,c.........'""--'..................
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum

C-H
C-H
I
H-C-H
I
C solvent
C
proton decoupled
i
200 160 120 80 40 o ,,(ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
284
Problem 196
IR Spectrum
(nujol mull)
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

139 0.5 CD
lJ
C
80
CD
c. -e'0"
60 M+" .c'"
'"
.c 91 154
1.0 '" UV spectrum
40 '0
<ft. 2.068 mg 110 mls
solvent: ethanol
__ 1.5 L..l-. """'-- .......- ......
40 80 120 160 200 240 280 200 250 300 350

m/e A(nm)
13C NMR Spectrum

solvent
TMS
proton decoupled
200 160 120 80 40 o (5 (ppm)
1H NMR Spectrum
TMS

I I 1 1 I I I I 1 I L
10 9 8 7 6 5 4 3 2 1 0
(5 (ppm)
285
Problem 197
IR Spectrum
(nujol mull)
1315
1150
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

156 M+' 0.5 Q)
o
172 c:
80 .x
l'll 92 l'll
Q) of
o, o
60 Q)
'"
..c
UV spectrum
'l'll" l'll
40 '0
..c
1.0 0.706 mg 110 mls
20 *' path length: 0.1 cm

solvent: ethanol
C 6H aS0 2N2
II ,IL .I, l
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

(15.0 MHz. o"O/OCI solution)
C-H
C-H
C C
proton decoupled
II
I I I I I I I
200 160 120 80 40 o s (ppm)
1H NMR Spectrum
(100 MHz, C0 3COC03 solution)
TMS
exchanges
slowly
with 0 20
solvent
10 9 8 7 6 5 4 3 2 1 o
(ppm)
286
Problem 198
r
IR Spectrum
(liquid film)
1320
1135
4000 3000 2000 1600 1200 800

V (cm'")
100 Mass Spectrum

75
80 ""co
Q)
c, No significant UV
60 Q)
(J>
'"
40 '0

o. M+" = 118 1%)
20
40 80 120 160 200 240 280

m/e
I I I I I I I I I I . , I
13C NMR Spectrum
proton coupled II I
solvent
proton decoupled
I I I I I I I I
I I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
I I I I
7.0 6.6 6.2 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
287
Problem 199
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

139 0.5
80 .>t.
<ll \,I
Q>
c. M+'
60 Q>
Ul
180 UV spectrum
<ll
..c
40 15 1.0 0.284 mg 110 mls
path length: 0.5 cm
<flo
201- solvent: ethanol
11.11, .b Il .1. C10H12OS

1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

C-H
C-H I
I -CH 3 H-C-H
I
H-C-H
I
C-H
C TMS
C
l
I I II
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
288
Problem 200
1355
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (cm'")
100 91 199 Mass Spectrum UV Spectrum

\J
80 ..><
<II
Q)
Q. Amax 225 nm (I091OE 4.6)
60 Q)
l/l 155 C22H3009S2
<II
.0 Amax 260 nm (I0910E 3.3)
40 '0
M+ = 502 (<1%)

20 243
287 331
Amax 272 nm (I091OE 3.1 )
1,1 II II I I
solvent: methanol
40 80 120 160 200 240 280 320

mle
13C
I
NMR Spectrum
I

I I I I r -r
Tn-
I I T
expansion
I
70 68 ppm I
DEPT CH 2 1 CH 3t CHt

,
proton decoupled
solvent
70 I
I
I I LI
68 ppm
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
- - - I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
289
Problem 201
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

63
80 43
Q)
Q.
60
'"
..c
M+" absorption above 220 nm
40 '0 106/108
ate 65
20
I. II
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

I
H-C-H
I I
C-H H-C-H
I I
H-C-H
I
TMS
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(100 MHz. c, o, solution)
<
20 Hz r'
TMS
.:
I----t
expansion
,
r-- solvent - .:
I residual
4.0 ppm
II
r----
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
290
Problem 202
(
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (cm")
100 M+' Mass Spectrum

189
80 "'IJl'o,""
107
60 IJl
II) 55
40 '0
'"
.c
(fl. .. 91
20
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
I
solvent
proton decoupled I I
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
r---
I---
TMS
-
n I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
291
Problem 203
IR Spectrum
(liquid film) 1136
4000 3000 2000 1600 1200 800

V (cm'")
80 .><
'I"II
0-
60 III
''""
91
.t:>
40 '0
;f?
20
II,
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
/proton decoupled
I I
200
I
160
I I
I I
120
I
solvent
80

I
I
I
I
40
I I
0
I
3 (ppm)
expansion
1H NMR Spectrum
expansion
5.14 5.10 ppm 4.0 3.8 ppm 3.06 3.00 ppm
7.3 7.2 ppm TMS
10 9 8 7 6 5 4 3 2 1 o
3 (ppm)
292
Problem 204
IR Spectrum 1695
(liquid film)
1670 J
4000 3000 2000 1600 1200 800 0.0
V (ern")
100 Mass Spectrum

131 0.5 II)
o
80 "" c
'c-"
II)
o
'"
60 II)
II)
II)
..c
40 '5
'"
..c
103 1.0 '"
<ft. 77 M+" UV spectrum
20 174
1.1 "I .l J I C 12 H 14 0
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum

5x C-H
1 xC
-CH 3
I
-CH
I
proton decoupled
TMS
lC
l 1
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1
l
0
o(ppm)
293
Problem 205
1630
IR Spectrum 1680
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (em")
100 Mass Spectrum

77 0.5 CD
0
131 c:
80 "'<tl"
CD
a. M+

0
'"
60 InCD 103 .c
In
132
'"
.c
1.0 '"
40 '0
o?-
20
,III .1,'111 l CgHaO
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum

- - Resolves into
(50.0 MHz, CDC1 3 solution) two signals at higher field
expansion
i i
150 130 ppm
- - Resolves into
expansion two signals at higher field
, ,
200 160 120 80 40 o 8 (ppm)
1H NMR Spectrum
expansion
I , i
9.0 8.0 7.0 ppm
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
294
Problem 206
IR Spectrum
3340 (liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

\I
80 -'"
III 91 M+
<I)
a. 78 134 Amax 250 nm (Io91Oc > 4.0)
60 <I)
l/l 105
III
J:J 77
40 '0
?ft:.
20
C gH1QO
40 80 120 160 200 240 280
role
13C NMR Spectrum - Resolves into
I
- - Resolves into
solvent
I
proton decoupled
200 160 120 80 40 o o(ppm)
lH NMR Spectrum
(200 MHz, CDCI 3 solution) ,
exchanges
with D 20
expansion
I i
3.8 3.0
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
295
Problem 207
IR Spectrum
(CHCI3 solution)
4000 3000 2000 1600 1200 800 0.0

V (cm'")
100 Mass Spectrum

57 0.5
B
80 -'"
III
C
III
\I
<ll
a.

0
60 <ll
III
III
.c
III III UV spectrum
.c
1.0
40 '0 0.210 mg 110 mls
173
'*' path length: 2.00 cm
C13H 17CI
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

r- 0--- 5 x C-H
C-H C
solvent rh TMS
,.
proton decoupled
200 160 120 .80 40 o 0 (ppm)
lH NMR Spectrum
TMS
expansion
100 Hz
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
296
Problem 208
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn")

80
v
""l'll
OJ
77
Amax ::::I 250 nm (109101': > 4.0)
o,
60 OJ
.c'"
l'll
40 '0 M+' 182/184

-;fl..
20
JI
40 80 120 160 200 240 280

mle
13C NMR Spectrum

C-H
--- 2xC-H
expansion
A V
C-H I I I
C-H 135 130 ppm
C solvent
proton decoupled
1 I
I I I I i I I I I I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
r
8.0 7.0 6.0 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
29'i
Problem 209
1377
1461
IR Spectrum
(nujol mull)
4000 3000 2000 1600 1200 800

V (ern")

80 ..><
'C"D
c- M+"
60 Q)
<Jl 227/229
'"
.0
40 15 197/199
oR-
20
C aH 6 N0 2Br
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

I I
DEPT CH 2 CH 3t CHt
Resolves into solvent
!
two signals at higher field 1
'proton decoupled
I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
-
expansion --'
,.-
TMS
\..
--- U
I I I I
8.5 8.0 7.5 7,0 ppm
'-----' 1
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
298
Problem 210
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (cm'")
80 ""Cll
Ql
Q.
60 Ql
en
Cll
.c
40 '0

0"
20
,I .II
40 80 120 160 200 240 280
m/e
I I I I I I I T I I I I
13C NMR Spectrurm resolves into
.
2 separate peaks
(100,0 MHz, at higher field strength
COCI 3 solution) I
130 125 ppm

DEPT
CH 2 , CH 3t CHt

2 separate peaks
'
at higher lfield strength

II ,
1
proton decoupled
,
130
,
125 ppm
I
,
solvent
I I I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum Exchanges

(400 MHz, COCI3 solution) with 020
expansion
expansion
3.7 3.6 ppm

1.9 1.8
I
ppm
1: TMS
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
299
Problem 211
IR Spectrum
(KBr disc) 1700 1678
4000 3000 2000 1600 1200 800

V (cm'")

90
80 ""til
c-
Q)
118
Amax 276 nm (109108 3.1)
60 Q)
Amax
lJ)
til
.Q 228 nm (109108 3.9)
40 '0
;ft.
solvent: methanol
20
J.JJl '"-"-'-"'IL JI,' ..........-'------"
Ib
162
I
-'--_
M+"(180<1%) C
9H 80 4
40 80 120 160 200 240 280

mle

(50.0 MHz, COCI 3/C03SOC03 solution) two signals at
higher field
solvent
- - Resolves into
two signals at
higher field
TMS
decoupled
I I I I I
I I I I I
l solvent
I I
I
I
200 160 120 80 40 o o(ppm)
1H NMR Spectrum
TMS
exchanges
with 0 20
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
300
Problem 212
IR Spectrum 1756
(liquid film)
4000 3000 2000 1600 1200 800

V (crn")

v
80
Ql
C. Amax 232 nm (109 10 1:: 3.8)
60 M+"
'"
.0 194 Amax 300 nm (109 10 1:: 3.6)
40 0
solvent: methanol
20
"',.J.i. .1,,1.1 .Il I. C1OH1004
40 80 120 160 200 240 280

mle
10 9 8 7 6 5 4 3 2 1 o
3 (ppm)
301
Problem 213
IR Spectrum
(CHCI 3 solution)
4000 3000 2000 1600 1200 800 0.0

V (crn'")
100 M+" Mass Spectrum

235 0.5 CI>
l
352-362
80 .>< '"
c
til
til
Q)
0-
III,I ,
0
320 340 360 (x20)
60 Q)
III
III
.0 UV spectrum
til <II
40 '0
.0
165 1.0 0.934 mg 110 mls
;;t!.
g path length: 0.1cm
C 14 H gCI 5 Q. path length: 2.0cm
20
II, , J J I, l, .1 I.
1.5
solvent: ethanol
40 80 120 160 200 240 280 200 250 300 350

m/e A(nm)
13C NMR Spectrum

(20.0 MHz, CDCI3"solution)
C-H
C-H
C
001"" 1 C-H
TMS
protoh decoupled
C il C
l lil 1 l
I I I I I 1 1 I 1 I I I
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
302
Problem 214
IR Spectrum
(KBr disc) 1745
4000 3000 2000 1600 1200 800 0.0

V (em")

O.S B
80 .x: C aH S03CI 3 c:
C1l
C1l
Q) -e
o,
M+" = 254 - 260 g
60 Q)
<J) .0
C1l
UV spectrum
C1l
209
.0
1.0 1.592 mg 110 mls
40 15 path length: 0.2 cm

20 solvent: ethanol
1.S w....................................-.........-...........L.o..J..............-...........

40 80 120 160 200 240 280 200 2S0 300 350
m/e A (nm)
13C NMR Spectrum

(50.0 MHz. DMSO-D6 solution)
Resolves into solvent

two signals at higher field -
proton decoupled
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
(100 MHz, DMSO-D6 solution)
exchanges
with D20
1
1H
2H
TMS
1H
11.8 ppm
solvent
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
303
Problem 215
1515
IR Spectrum
1345
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

M+' 365/367/369 (1:2:1) < 1%
C8HgN04Br2
0.5 s
c:
80 ""
'"
Q)
0-
-e'"o
60 Q) en
en .0
286 288
'"
.0
1.0 '" UV spectrum
40 '0
;F.
0.494 mg /10 mls
solvent: methanol
1.5 .-..... ............
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

solvent
/
;'
proton decoupled
I I I
200 160 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
304
Problem 216
r
IR Spectrum
(KBrdisc)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

135
80 .><
co
CD
0.
60 CD
II>
co
.a
40 '0
cf!. '.
20
.IJ 1 II M+' =281 1%)
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

expansion
-- Resolves into
two signals at
higher field
130
I ,
120
L
ppm
solvent -- Resolves into
two signals at
higher field
I I
130 120
proton decoupled
200 160 120 80 40 0 a (ppm)
1H NMR Spectrum
expansion expansion
j
I
6.8 ppm 3.8
I I
3.4
A
,
ppm
I
1.8
I
1.4 ,J TMS
10 9 8 7 6 5 4 3 2 1 o
a (ppm)
305
Problem 217
Note: ozonolysis of this compound

IR Spectrum affords acetone
(liquid film) 1725
4000 3000 2000 1600 1200 800 0.0

V (cm'")
100 Mass Spectrum

99 0.5 1Il
o
80
C
III
\I
1Il
c,
-e0
60 3l 155 '"
.0
III UV spectrum
III
40
.0
'0
1.0 0.307mg 110 mls
M+ path length: 0.5 cm
C1QH 16 04
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13e NMR Spectrum

TMS
solvent
proton decoupled
J III
200 160 120 80 40 0 o(ppm)

1H NMR Spectrum
rr:
-
F -.-J TMS
I I I I I I
1 I I I
I I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
306
Problem 218
IR Spectrum
(liquid film) 1726
4000 3000 2000 1600 1200 800

V (cm'")

41
96
80 .x:
III
Q>
C.
60 Q> 1\10 significant UV
'"
III
.0
40 15 M+' = 125 1%)
?ft..,
20
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

I
I H-C-H
solvent
H-C-H I
I
C-H C
C TMS
I I I I
200 160 120 80 40 0 cS (ppm)
1H NMR Spectrum
20 Hz
10 9 8 7 6 5 4 3 2 1 o
cS (ppm)
307
Problem 219
IR Spectrum
(liquid film)
1725
4000 3000 2000 1600 1200 aoo 0.0

V (em")
ao ""
ell '"
0. 41
60 ell
<Jl
UVspectrum
'"
..c
0.401 mg /10 mls
40 '0
0
M+' path length: 0.2 cm
20
II., I I I
C5H a02
40 ao 120 160 200 240 2aO 250 300 350

role A. (nm)
13C NMR Spectrum

..........io.J'\o"......,......................
TMS
, solvent
proton decoupled
III !.
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
I
2.0 ppm
i
expansion 6.5
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
308
Problem 220
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

95 0.5 s
80 oX c
'"
Q)
Co M+" -e'"
60 Q) 110
Ul .a
40
'"
.a
(;
1.0 '" UV spectrum
?ft. .. 0.231 mg 110 mls

path length: 0.2 cm
20
solvent: hexane
II tI 1I11 II C aH 14
1.5w.......................................................................L............................u
40 80 120 160 200 240 280 200 250 300 350
m/e A(nrn)
13C NMR Spectrum

proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS

I I I I
1
, I I I
J I I I
10 9 8 7 6 5 4 3 2 1 0
o (ppm)
309
Problem 221
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum _

75
80 "'"
'" '"
Q. No significant UV
60 '"
(J)
'"
.0
40 '0 M+" =164 1%)
>'!.
0
20
1111 .1
40 80 120 160 200 240 280

m/e
13e NMR Spectrum

200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
TMS
A
I I I I I
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
310
Problem 222
IR Spectrum
(liquid film)
4000 3000 2000 1S00 1200 800

V (cm'")
100 47
79 Mass Spectrum
\I
80
Cll 103
<Il
0.
No significant UV
SO <Il
l/l 107
Cll
.0
81
40 '0 M+' = 1521154 1%)
?ft.,.
20 109
III I II, C SH1302CI
40 80 120 1S0 200 240 280

mle
13C NMR Spectrum

proton coupled
solvent
proton decoupled
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
expansion
I I
4.0 3.0 2.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
311
Problem 223
IR Spectrum
(liquid film) 1094
4000 3000 2000 1600 1200 800

V (cm'")
100 91 181 Mass Spectrum UV Spectrum

80 -"
III
<ll 107 log108 between 2 and 3
c-
60 <ll
/Jl
III
.0
solvent: methanol
40 '0
?f.
20
"
40 80 120 160 200 240 280

mle
13C NMR Spectrum ......- resolves into 2 signals

at higher field
DEPT CH2 CH 3t CHt .....- resolves into 2 signals

al higher field
rI solvent """J..
proton ,decoupled
I I II
200 160 120 80 40 0 () (ppm)
lH NMR Spectrum
expansion
expansion
4.0 3.8 3.6 ppm
Exchanges with
7.4 7.3 ppm D20
TMS
I
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
312
Problem 224
IR Spectrum
(liquid film) 1580
1438
4000 3000 2000 1600 1200 800

V (ern")

\I
80 -"
C1l
Ql
Co
Amax 257 nm (10910 3.4)
60 Ql
Ul
C1l
J::l
Amax 270 nm (10 9 ' 0 2.6)
40 '0
<f1. solvent: methanol
20
40 80 120 160 200 240 280
JLJ
m/e
13C NMR Spectrum

proton coupled
____
,PI W.,.,
_._.,
t "' . . . .

proton decoupled
II
I I
200 160 120 80 40 o 0 (ppm)
'H NMR Spectrum

expansion

I-- , , , , , , , , , , ,
7.2 TMS
- 8.8 8.0 ppm
-
- -
I
10 9 8 7 6 5 4 3 2 o
o(ppm)
313
Problem 225
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (crn'")
100 M+' .Mass Spectrum

93
0.5 CIl
o
80 ..>:: <:
III
'"
CIl
a.
0
60 CIl
Ul
Ul
.0
III
UV spectrum
III
40
.0
'0 66
1.0 0.636 mg I 10 mls
<F-
J path length: 0.5 cm

20 92 solvent: methanol
II ,II, ' C SH 7N
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
I I I I I I
13C NMR Spectrum
III l
I
,
I
proton decoupled
I I
J
I I I
solvent
I I I I
G J
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
3H
TMS
2H 2H
A j
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
314
Problem 226
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (ern")
100 UV Spectrum
Mass Spectrum
v
80 -'"'
co
<ll
Co
66
Amax 262 nm (10 9 10 E 3.6)
60 <ll
Vl
co
.0
solvent: methanol
40 '0
o , .' 78
20
J j J
40 80 120 160 200 240 280
m/e
C-H
13C NMR Spectrum C-H C-H
C-H
solvent
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
I
8.6
I
8.4
I I
7.4
I
'-J
I
7.0 ppm

, - TMS
1 Ii I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
315
Problem 227
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (cm'")

M+'
93
80 tii
Q)
o,
66
Amax 263 nm (Io91O E 3.5)
60 gs
40 '0
'"
20
II II" dl
40 80 120 160 200 240 280

mle
13C NMR Spectrum
___W_ _L
I solvent
proton decoupled I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion with
(400 MHz)
in acetone- d6
solution
I I I I I
8.6 . 8.4 7.6 7.4 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
316
Problem 228
IR Spectrum 1690
(liquid film)
4000 3000 2000 1600 1200 800

V (em")

106
80 .><
v
'0-C"D "'max 228 nm (I091OE 3.9)
60 CD
(IJ
M+" = 121
43
'"
.t:J "'max 267 nm (I0910E 3.5)
40 '0
0
r solvent: ethanol
20
I
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

------'w"--------_
__
200 160 120
solvent
80 40 o 0 (ppm)
1H NMR Spectrum
9.11
.' ,
9.01 8.62 8.72 8.17 8.07
Jl
7.37 7.27
-

I
I JI -
TMS
I
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
317
Problem 229
IR Spectrum
(liquid film) 1745
4000 3000 2000 1600 1200 800 0.0

V (cm'")
100 Mass Spectrum

106 0.5
80 .>t:
""
Ql
Q.
60 Ql
til 78 M+' UV spectrum
165
""
40 '0
.0
1.0 0.479 mg /1 0 mls
path length: 0.2 cm
20 solvent: ethanol
11,11 I C 9H 11N02
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A (nm)
13C NMR Spectrum

C-H C-H
C-H C-H C-H
C TMS
l
/ C solvent
protorydecoupled
,/
! III
200 160 120 80 40 0 o(ppm)

lH NMR Spectrum TMS
9.0 8.5 8.0 7.5 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
318
Problem 230
3400
IR Spectrum
(CHCI 3 solution)
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

0.5 v
80
80 .>< 81
M+'
'c.4l" 108
60 4l
lJ)
UV spectrum
40
'"
.J:J
'0
1.0 0.159 mg 110 rnls
';j!. .. path length: 1.00 cm

20 solvent: ethanol
I III JII IJ C 6H 8N 2
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

TMS
solvent
proton decoupled
III J
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
TMS
exchanges
with D?O
10 9 8 7 6 5 4 3 2 1 o
a (ppm)
319
Problem 231
IR Spectrum
(liquid film)
1587
4000 3000 2000 1600 1200 800

V (cm")

M+"
80 .>e.
94 V
'"a.CD Amax 270 nm (10 9101': 2.5)
60 CD
til
'"
.c Amax 240 nm (1 0 9 10 1': 3.4)
40 '0 53 67
cf?
J .J 7
9
C5 H6 N2
II 1
40 80 120 160 200 240 280

mle
13C NMR Spectrum

(50.0 MHz, coo 3 solution)
I
DEPT CHzt CH 3t cHt
I solvent
,
I
I
protondecoupted
200 160 120 80 40 o a (ppm)

1H NMR Spectrum
_J _t-=pans:Jl_ j
9.0 8.4 ppm 7.6 7.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
a (ppm)
320
Problem 232
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800 0.0

V (cm'")
100 Mass Spectrum

0.5 fl
91 c
80 .>:: ctl
ctl
Q)
c.
-eo
60 Q)
III
III
.0
ctl ctl
.0
1.0 UV spectrum
40 '0
;#. '. 39 65 2.396 mg / 10 mls
solvent: hexane
.................. ...o....JL..._........L._................................o....J'__'_.....L._............
L....----'-................... ' _'_..L_..o.............o....J.............. 1.5 1-1-0-............................. -........-..-'-...........-...........................
40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum

r -, 3 x C-H
expansion 1x C-H
1x CH2
C
I
130 ppm
TMS
proton decoupled
200 160 120 80 40 o 0 (ppm)

I I i
4.0 3.0 2.5 ppm
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
321
Problem 233
expansion expansion
JL
i
6.75
i
6.70 ppm

_JL
i
2.25
i
2.20 ppm

TMS
I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
322
Problem 234
IR Spectrum
(KBr disc) 1692
4000 3000 2000 1600 1200 800 0.0

V (crn'")

0.5 Ql
o
c:
80 -'"
<'ll <'ll
Ql
0-

0
60 Ql
II)
M+" II)
.Q
<'ll 112 <'ll
40 '0
.Q
1.0 UV spectrum
o , 0.462 mg /10 mls

II uJ ,I, ,I. I CS H 40 3 solvent: ethanol

1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13e NMR Spectrum

off-resonance decoupled J- TMS
solvent
proton decoupled
200 160 120 80 40 0 /0 (ppm)
1H NMR Spectrum expansion TMS

(100 MHz. COCI 3 solution) I I
100 Hz
j j[- CHCI
3
JL
J
.,oh'09'
with 0
___
20

,-J

11.3 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
323
Problem 235
IR Spectrum
(liquid film)
1677
4000 3000 2000 1600 1200 800 0.0

V (crn")

0.5 G)
95 u
80 .:.f. c:
'c."
G) '0"
of
60 G)
"'
.J:J
"'
'"
.J:J
M+" '"
40 '0 152 1.0 UV spectrum
*- 0.214mg/10mls
20
.,,1 I I II L C 9H 1202
1.5
path length: 0.5 cm
40 80 120 160 200 240 280 200 250 300 350

m/e A (nm)
13C NMR Spectrum

proton decoupled solvent TMS

I
200 160 120 80 40 o 0 (ppm)
I
1H NMR Spectrum 50 Hz
I
CHCI3
expansion

\. .Iv..
,- - v-r-r-r-:

TMS
----1
I I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
324
Problem 236
IR Spectrum
(CHCI3 solution) 1510 1320
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

0.5
80 .><
'"
Q)
0-
60 Q)
Ul M+"
82
40
'"
..c
'5
174
1.0 UV spectrum
c/!. . . 0.210 mg 110 mls
11.11 ,I I C4H2N20 4S solvent: ethanol

1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
13C NMR Spectrum

TMS
solvent
proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum TMS

expansion
25 Hz
I I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
325
Problem 237
1675 1515
IR Spectrum
4000 3000 2000 1600 1200 800 0.0

V (ern")
100 Mass Spectrum

156 0.5 .,
(;
c
80
<II <II
Q)
o,
o
60 Q)
til
til
.J:> UV spectrum
<II <II
.J:>
.110 M+" 1.0 2.306 mg I 20 mls

solvent; dioxan
20
40 80 120 160 200 250 300 350

mle A(nm)
13e NMR Spectrum

solvent
off-resonance decoupled TMS
proton .l
.",
.L "
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum TMS

6H
326
Problem 238
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (cm'")
I
12 ppm
,--
r-- -
-
---- TMS
I
109 8 7 6 5 4 3 2 1 0
o (ppm)
327
Problem 239
IR Spectrum
(KBr disc)
4000 3000 2000 1S00 800

V (cm'")

80 :
'"
<Il
0. Amax 22S nm (l091Of: 4.4)
SO <Il
rJ>
'"
.0 Amax 256 nm (l091Of: 3.7)
40 '0
<f!.
20 Amax 288 nm (1091Of: 3.3)
I," II , Iii
Amax 297 nm (10910 f: 3.5 )
40 80 120 1S0 200 240 280
solvent: ethanol
m/e
I I I I I I I I I I J I
13C NMR Spectrum
(100.0 MHz, CDCI 3 solution) expansion
j 1, 1
, , ,
DEPT CH,. CH 3t CHt 126 122 ppm
proton decpGpled
/
I I
X"
, ,
140.5
I
140.0
,
I
ppm
,
I
I I
-ClU--L
,
I
,
126
I
,
I - - solvent
I ,
,
122 ppm
, I
200 160 120 80 40 o 3 (ppm)
1H NMR Spectrum
expansion
8.0 7.8 7.6 7.4 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
cS (ppm)
328
Problem 240
IR Spectrum
3402 (KBr disc)
4000 3000 2000 1600 1200 800

V (cm'")
80
Q)
0- Amax 229 nm (lo910f: 4.4)
60 ill
'"
.c Amax 284 nm (lo910f: 3.8)
40 '0
cf?..
solvent: ethanol
20
I
40 80 120 160 200 240 280

mle
I I I I I I I I I r -1 T
13C NMR
Spectrum
, , , ,

, , ,
DEPT
(100.0 MHz, 140 130 120 ppm 24 22 ppm CH2 t CH 3+ CH+

COCI3 solution)
expansion
,
II
,
I
, i , ,
j
i
140 130 120 ppm 24 22 ppm

solvent
proton decoupled I
II I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
Exchanges
with 020
. I
7.8 7.5 7.2 ppm

TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
329
Problem 241
IR Spectrum
(liquid film)
1796
4000 3000 2000 1600. 1200 800

V (em")

43
80 ..><
III
Q)
a.
60 Q)
'"
III
.0 M+" solvent: ethanol
40 '0 98
20
*- I'
,11 III ,I I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

(50.0 MHz, CDC1 3 solution)
I
DEPT CH2 t CH3 t CH t
1H NMR Spectrum
expansions
-L , , , , ,
.:
, , , , ,
"
, , , '-------
, ,
V-
V--
TMS
5.3 5.0 ppm 3.3 3.0 ppm 2.2 1.8 ppm
-
r-

I I I I I I I 1 I I I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
330
Problem 242
IR Spectrum 1760
(liquid film)
4000 .3000 2000 1600 1200 800

V (em")
80 -'"
III
e
C.
60 'll No significant UV
<Il
III 72
J:l absorption above 220 nm
40 '15 M+"= 100

20
i d I CSHa0 2
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

proton decoupled
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansions
-.,-----,---..- -.,-----,---.... -....----.- ---,---..---

4.35 4.30 4.10 4.05 3.80 3.75 2.6 2.5
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
331
Problem 243
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (cm")
100 Mass Spectrum

42
80 -'"
''a""-
'"
l /l
'"
40 '0 56
oft
20
I..i ,II
40 80 120 160 200 240 280

m/e
,j
NMR Spectrum
JL
13C
L
proton.decoupfed
I
(
I
L I I I I I
solvent
I I I I
TMS
200 160 120 80 40 0 o (ppm)
1H NMR Spectrum
(100 MHz and 400 MHz, CDCI 3 solution)
400 MHz
TMS
I I I
4.36 2.48 2.28
expansions at 400 MHz
1
10 9 8 7 6 5 4 3 2 1 0
o (ppm)
332
Problem 244
IR Spectrum 1722
(KBr disc) 1751 Note: this compound has no
significant dipole moment
4000 3000 2000 1600 1200 800
V (ern")
100 Mass Spectrum

42 70
.- V
80 "''""
Q)
0-
60 Q)
en
No significant UV
'"
.c M+'
40 '0
o "
20 ,
,I .d. CaH 120 2
40 80 120 160 200 240 280
m/e
L
13C NMR Spectrum
_I l1J
TMS
proton decoupled
solvent I
l I
200 160 120 80 40 o s (ppm)
lH NMR Spectrum
(100 MHz, CDCJ3 solution)
TMS
I
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
333
Problem 245
IR Spectrum
(nujol mull)
4000 3000 2000 1600 1200 800

V (crn")
100 Mass Spectrum
80
+"
(\)
0-
158
186
60
40 '0
'"
.0
20 *
C 14 H18
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

1
r
/ , solvent
proton Iclecoupled
I
200 160 120 80 40 o 0 (ppm)
TMS
1H NMR Spectrum
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
334
Problem 246
IR Spectrum 1680
(KBr disc)
4000 3000 2000 1600 800

V (cm")

180 V
M+"= 208
80 .:.<
III
Q)
a.
152
A. max 255 nm (109108 4.7)
60 Q)
VI
III
.0 A. max 275 nm (1091084.3)
40 '0
?fi.-'
A. max 330 nm (1091083.8)
20
l J 1 ,I J
solvent: ethanol
40 80 120 160 200 240 280

mle
I I I I I
expansion
I r I I I
U
13C NMR Spectrum
(100.0 MHz, CDCl a solution)
DEPT CH 2 1CHat CHt ,

135 130
, i
ppm
expansion
proton decoupled
I
U
,
135 130
i ,
ppm
solvent
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansions
l- I--
solvent
residual J J Itt
1 8.4 8.3 8.2 ppm 7.9 7.8 7.7 ppm
TMS
- -
I I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
335
Problem 247
IR Spectrum
(nujol mull)
4000 3000 2000 1600 1200 800 0.0

V (em") ,i;}
100 Mass Spectrum

0.5 Q)
o
80 c:
"'c."
l'll
Q)
v
l'll
-e0
60 Q)
Vl
Vl
.c
l'll
.c M+" l'll
40 '0 240 1.0 UV spectrum
* 8.148 mg /10 mls
l
d ,J I.. ,1,1 IlL .Ii C 18H 24 solvent: hexane
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A (nm)
13C NMR Spectrum

1
I
, solvent
TMS
I
proton decoupled
I I I
200 160 120 80 40 a 0 (ppm)
1H NMR Spectrum
TMS
I I I I I I I

, I I I
10 9 8 7 6 5 4 3 2 1 a
o(ppm)
336
Problem 248
IR Spectrum
(nujol mull)
4000 3000 2000 1600 1200 800

V (crn'")

80 .>t:.
'"
Q)
o,
M+' Amax 249 nm (10 9 10 8 5.0)
228
60 Q)
Amax 257 nm
Ul
'"
.0 (10 9 10 8 5.2)
40 '0
(/:. .. Amax 273 nm (109108 4.4)
20
solvent: ethanol
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

C-H
C-H
solvent
I I I I I I I I
I I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
J l ) l
I I I I I
8.5 7.5 ppm
TMs
0'
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
Problem 249
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

43
80 "''""
Q)
C-
(J)

40 '0

20
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

III
r
," TMS
solvent
proton decoupled j l
I I I I I I I I I I
200 160 120 80 40 o () (ppm)

lH NMR Spectrum
-
- TMS
Jf
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
338
Problem 250
IR Spectrum
(CHCI 3 solution)
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

55 V
80
Q) No significant UV
c-
to
..0
40 '0 82
20
40 80 120 160 200 240 280

m/e
13C NMR

(20.0MH'_ COCI,
I I
4 X H-C-H
I
TMS
solvent
proton decoupled
il!
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
4H
4H
exchanges
with 0 20 lH
TMS
I I I I 1 , I I I I I
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
339
Problem 251
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (ern")

80 ;'g
Q)
c.. Amax 310 nm (10910 1.2)
60
'"
..c solvent: isooctane
40 '0
20
40 80 120 160 200 240 280

mle
13C NMR Spectrum
(100,0 MHz, COCI 3 solution)
- - Resolves into two

signals at higher field
,
solvent
I
I - I I I I I I I
200 160 120 80 40 o 0 (ppm)

expansion
(400 MHz, COC'3 solution)
Exchanges
with 020
,
2.4 2.2 ppm 1.6 1.4 ppm TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
340
Problem 252
3212
IR Spectrum
(KBr disc) 1658
4000 3000 2000 1600 1200 800

V (crn")
100 55
Mass Spectrum
V
80 "'C1l"
Ql
a.
60 Ql Vl
M+"
C1l
.c 84 113 absorption above 220 nm
40 '0 85
'.
20
1.1 k. C 6H 11 NO
40 80 120 160 200 240 280

mle
13C NNiR Spectrum

[fll

proton decoupled
solvent
__ lW_.
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
3.0
I
2.0
l ---
ppm
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
Problem 253
4000 3000 2000 1600 1200 800

V (ern")
100 Mass Spectrum

58
80 .x:
<ll
Q)
C-
III
<ll
on absorption above 220 nm
40 '0
<ft.
20 88 M+'
119
III ,Il I
40 80 120 160 200 240 280

mle
13C NMR Spectrum

(50,0 MHz, COCI 3 solution)
I
I
solvent
proton decoupled
W
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum 6H
(400 MHz, COCI 3 solution) expansions
30 Hz
r---l
1H 1H 1H 1H 1H
I I I
-JL I

I
3,79 3.66 3.49 2.50 ppm 2.22 ppm
2H exchanges TMS
with 0 20 __
An * I
I I I I I I I - I I I I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
342
Problem 254
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (cm")

80 sc
v
III
Ql
0- Amax 258 nm (lo91QE 2.3)
60 Ql
CIl
III
.0
40 '0 solvent: methanol
M+' =165 1%)
20 *' '.
105
I. l J
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton decoupJed .
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion i i I I
4.4 4.0 2.8 2.4 ppm I
1.2 0.8
2H near l) 2.6
exchange
with 0 20
I TMS
7.6 7.2
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
343
Problem 255
IR Spectrum
1666
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

80 .><
'<C."Il
60 <Il
Ul
No significant UV
'"
.0
40 '0 86 .
?t-
M+'
20

101
II I 1
CSH 11NO
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

,.-
--
pj-oton decoupled --Ju solvent

__A..__ _.....ll.-_-J.L _
200 160 120 80 40 o <5 (ppm)
1H NMR Spectrum 1H -
j I
1H
I I

expansion expansion exchange r -, 9H
with D 2 0 on warming
t t

I I I I I I I
8.4 8.0 ppm 8.0 7.0 6.0 ppm
TMS
I
II
10 9 8 7 6 5 4 3 2 1 o
<5 (ppm)
344
Problem 256
3376
IR Spectrum 1718
(KBr disc) 1590
2548
4000 3000 2000 1600 1200 800

V (crn'")

v
80
Q) No significant UV
a.
1-2
40 '0
of?
20
I, 1.1 j .1,
M+"= 163
CS H gN0 3S
40 80 120 160 200 240 280

m/e
13C NMR Spectrum
(100.0 MHz, CDCI 3/DMSO-d6 solution)
I
DEPT CH2 f CHJt CHt
solvent
lTI
f
proton decoupled
I , I I I I I I
I I I
,
o
,
200 160 120 80 40 0 (ppm)
expansions
1H NMR Spectrum
(400 MHz, CDCI3/DMSO-d6 solution) expansion
, withD20
i i i i i i
11.0 10.0 9.0 ppm 7.7 7.6 4.8 4.7 3.0 2.9 ppm
1.8 1.7 ppm
r note broad
signal
TMS
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
345
Problem 257
Note: irradiation of the signal at Ii 6.58 in the

IR Spectrum
(KBrdisc) 1H NMR produces an enhancement of the
signals at Ii 6.66 and 4.45 ppm via the NOE
4000 3000 2000 1600 1200 800

V (crn")
80
Ql
C. Amax 220 nm (Io910E 3.8)
60 3l
40 '0
<ll
.n Amax 280 nm (Io910E 3.4)
solvent: H 2 0 pH 7
20
40 80 120 160 200 240 280

m/e
13e NMR Spectrum

(100.0 MHz, 0 20 solution)
resolves into 2 peaks

at higher magnetic fields
proton
..
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum 2H
(400 MHz, OMSO-d6 solution)
1H 3H
L- solvent
Note: there are 4 exchangeable residual
protons which appear
with the residual H 2 0
1H
residual H 2 0
1H in solvent
1H
2.6 2.5 ppm
4.5 4.4 ppm
TMS
6.8 6.7 6.6 ppm
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
346
Problem 258
IR Spectrum
(KBrdisc)
3405 1667
4000 3000 2000 1600 1200 800

V (crn'")

\I
80 .>t!.
'"
OJ
o, Amax 220 nm (10910 4.6)
60 OJ
<J)
'"
.0 Amax 273 nm (10910 3.8)
40 '0

20
0"
Amax 280 nm (10910 3.8)
Amax 289 nm (10910 3.7)

40 80 120 160 200 240 280 solvent: methanol
m/e
13C NMR Spectrum
(100.0 MHz, D20 solution)
proton decoupled
J I I
200 160 120 80 40 o 0 (ppm)
lH NMR Spectrum
(400 MHz, D20 solution)
expansion
Note: there are 4 exchangeable
protons which appear
wilhthe residual H 20
H20 and HOD

.t: expansion
1L
in solvent
, ,
4.4 4.2 ppm 3.4 3.2 ppm
7.5 7.0 ppm
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
347
Problem 259
3276
IR Spectrum
1702
(KBr disc) 1666
4000 3000 2000 1600 1200 800

V (cm'")

43
80 '"'"
Ql
c.
60 Ql
Vl
D'"
40 '0 ,
;ft.
20
!. ,II I I
40 80 120 160 200 240 280

m/e
I I I I I I J I I I I
13C NMR Spectrum
Il
proton decoupled
/
,
solvent
I
I
I I I
I I I I I I
I
I I I I
200 160 120 80 40 0 () (ppm)
expansions
1H NMR Spectrum
Jul JL
'"
expansion
r
f
expansion
, , , , ,
4.6 4.5 ppm 3.4 3.2 ppm 2.8 2.7 ppm
l"
Jl 6.8 6.7 ppm
Exchanges
with 020
S
---. ,
2.0
,
1.9 ppm
TMS
f
I
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
348
Problem 260
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (cm")

\,I
80 "'<tI"
Ql
a.
Vl
<tI
.D absorption above 220 nm
40 '0

0,.
20 102
JJ J I
M+"= 147 1%)
CSH gN0 4
40 80 120 160 200 240 280

m/e
I I I I I I I I I I
13C NMR Spectrum

(100,0 MHz, 020 solution)
," .
DEPT CHz' CHat CHt
proton decoupled
I I I
I
I I I I I I
l I I I
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
(400 MHz, 020 solution) H20 and HOD
in solvent
Note: there are 4 protons I
which exchange with

the 020 solvent
L-
expansions
r-r-- ,.-

4,2
i
4.0
i
JL
i
2,9
i
2,7 2.4 2,2 ppm

- ---' -'
'--'
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
349
Problem 261
IR Spectrum
(liquid film) 1715
4000 3000 2000 1600 1200 800 0.0

V (cm'")
100 Mass Spectrum

44 0.5 CD
o
c:
80 "'"
sc-
ttl
o
60 58 III
.0
ttl
2 1.0
40 '0 UV spectrum
20 *" 49.5 mg 110 mls

solvent: hexane
40 80 120 160 200 240 280 250 300 350

m/e . A(nm)
13C NMR Spectrum

(20.0 MHz, CDCl a solution)
I
H-C-H
I
proton decoupled C-H

C-H TMS
/ solvent
III I
, I I I I I I I I I I I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(100 MHz, CDCl a solution)
expansion
of 400 MHz spectrum
20 Hz
9.75
I
2.31 2.21
I
J TMS
J
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
350
Problem 262
IR
(liquid film)
3000 1200;-""---......J----
800 '
4000
80 ""
'a.<"1l
No significant
. UV
60 <1lVI
'"
40 '0
?fi. "
20 M+"-- 130 1%)
40 80 120 160 200 280

m/e
13e NMR
(1000 M Spectrum
. Hz, CDCI 3 solution)
proton decoupled
o o(ppm)
1H NMR S
(400 M pectrum
J- II 48 4.7 ppm ,:, ':5 ':4 ppm ,:, ,:

,
,pm
5.8 5
. 7ppm
' ,
5.3 5:2 JJJ
f TMS
8 7 6 5 4 3 2 0
o(ppm)
351
Problem 263a
IR Spectrum
(liquid film)
A 400 MHz 1H NMR spectrum (with expansions)

is given on the following page
4000 3000 2000 1600 1200 800

V (cm'")
100 28 30 56 Mass Spectrum

80 sc
'C"D
0-
60 CD
rn
No significant UV
'" M+"
.0
40 '0
*-
20
jJ C 3H 7N
40 80 120 160 200 240 280

mle
13C NMR Spectrum

I
I
H-C-H H-C-H
I
I
C-H
TMS
, solvent
prdton decoupled
I I I I I
III
I I I
l
I
I I I
200 160 120 80 40 0 o (ppm)
1H NMR Spectrum
l
(100 MHz. COCI 3 solution) exchanges
expansion with 0 20

,
AM
5.0
, i
6.0 4.0 ppm
Jf TMS
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
352
Problem 263b
1H NMR Spectrum 2H
2H
exchanges
with 0 20
2H
1H
7 6 5 4 3 2 1 o
o (ppm)
Expansion of regions
of the 400 MHz NMR spectrum
5.996 ppm
20.0 Hz
5.152 ppm 5.040 ppm 3.307 ppm
353
\
.s: Problem 264
'f l 1
IR Spectrum
(CHCI3 solution)
I I I I I I
4000 3000 2000 1600 1200 800
V (ern")
100 Mass Spectrum

80 -'"
M+' = 136
'"
Ol
c-
60 Ol
Ul
No significant UV
'"
.a absorption above 220 nm
40 '0
;i<.
20
1 II I C1QH 16
1H NMR Spectrum
{
expansion
/
i
/ '-----, i ,
1.'9 1.7 ppm
TMS
! I
I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
a (ppm)
354
Problem 265
IR Spectrum
(CCI 4 solution)
4000 3000 2000 1600 1200 800

V (crn'")

80 "''""
Q)
0.
60 Q)
(Jl
No significant UV
40 "6
.D

M+" = 118 1%)
20 103
III I I I C6H 140 2
40 80 120 160 200 240 280

m/e
I I I I I I I I I I
13C NMR Spectrum
I
[
I
proton decoupled
200
I I
160
I
120
I I
solvent
L-I
I
80
W I I
40
I I
0 o(ppm)

with irradiation
(400 MHz, COCI3 solution) at 64.0 PPM
expansion
, i
expansion 4.05 3.95 ppm 1.5 1.3 ppm

expansion
Exchanges
with 020
,
4.4 4.0 ppm L 1.4 1.0 ppm
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
355
Problem 266
Note: irradiation of the signal at /) 6.45 in the

IR Spectrum 1H NMR produces an enhancement of the
(liquid film) signals at Ii 3.4 and 3.7 ppm via the NOE
4000 3000 2000 1600 1200 800

V (cm'")

M+"
80 """ 164
'QC-"l A. max 281 nm (109108 3.5)
60 Ql <J)
'"
J:l
55
77 149 A. max 230 nm (109108 3.6)
40 '0 103

solvent: methanol
20
40 80 120 160 200 240 280

mle
I I I I I I I I I I f I
13C NMR Spectrum
I
DEPT CH2 1 CH 3t CHt
,I
I
I
proton decoupled
I I I I
II
I
1 I
solvent
I
II
I I I
200 160 120 80 40 o 0 (ppm)

(200 MHz, COCI3 I C 606 solution)
exchanges

expansion
expansion
with resolution enhancement
I I
6.0 5.0 ppm
I
7.0
10 9
356
Problem 267
IR Spectrum
(CCI4 solution)
4000 3000 2000 1600 1200 800

V (ern")

203/205
V
80
<1l 109108 > 4.5
Q)
c. M+" 218/220
60 Q)
U)
<1l
.0
40 a
"#. .. 183
20
I I I .1 L .Il ,Ih, 1.1 I C14H15 CI
40 80 120 160 200 240 280

mle
13C NMR Spectrum

solvent
proton decoupled
200 160 120 80 40 o 8 (ppm)
lH NMR Spectrum
(300MHz, CDCI 3 solution)
expansion
I I i iii i i
7.0 6.5 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
357
Problem 268
4000 3000 2000 1600 1200 800

V (cm'")
100 Mass Spectrum

43
80 .><
CD
<D
0-
60 <D
lI)
No significant UV
CD
40 '0
*-
20
I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton'decoupled
I I
200
I
178
160
I
176 ppm
120
L.a, J , .
I
80
I I
lJJ
I
40
I
It,
0
I
o(ppm)
1H NMR Spectrum
(400 MHz. 020 solution) H20 and HOO
in solvent
which exchange with
the 020 solvent
L
expansions

""
II ,
4.9
,
4.7 ppm
, ,
3.0 2.9 ppm
L

10 9 8 7 6 5 4 3 2 1 0
o(ppm)
358
Problem 269
4000 3000 2000 1600 1200 800

V (ern")
80 -'"
co
'"
C-
No significant UV
60 '"co
l/l 102
40 '0

0
126 144
20
I l. I
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

(100.0 MHz, D20 solution)
200 160 120 80 40 0 o(ppm)
1H NMR Spectrum
H 20 and HOD
(400 MHz, D20 solution) in solvent
which exchange with L
the D20 solvent

J
, ,
-f
I I r- i i
4.3 4.2 2.4 2.2 2.1 1.9 ppm
- ...-
J I I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
359
Problem 270
IR Spectrum
3547 (KBr disc)
4000 3000 2000 1600 1200 800

V (crn'")

192
80 -'"
'"
Q)
o,
60 Q)
In
147
'"
.D
40 '0
<f?
20
40 80 120 160 200 240 280

m/e
I I I I I I I I I J I I
13C NMR Spectrum
DEPT CH2 1CHA CHt
solvent
/
proton-decoupied
L
I I I
II
I
I I
I I
II
I I
I I I I
"
200 160 120 80 40 o s (ppm)
1H NMR Spectrum expansions

Note: there is a broad signal

at 11.5 ppm (1 proton) i i
which exchanges 1.4 1.2 ppm

with 020 , , , , , , , ,
6.2 6.0 5.0 4.8 4.3 4.1 3.1 3.0 ppm
Exchanges
with 020
1
TMS
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
360
Problem 271
IR Spectrum
(liquid film) 2851
1077
4000 3000 2000 1600 1200 800

V (cm")

41
\.I
80 -'"
<II
Ql
0.
60 Ql
C/)
M+" No significant UV
<II
.D.
70
40 '0 absorption above 220 nm
.
o
20
,II C 4H 6O
40 80 120 160 200 240 280

m/e
13C NMR Spectrum

proton coupled
j
proton decoupled solvent m

200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
.----

----'
- TMS
I
10 9 8 7 6 5 4 3 2 1 0
o(ppm)
361
Problem 272
IR Spectrum
(liquid film) 1620
4000 3000 2000 1600 1200 800

V (crn'")
100 Mass Spectrum

41
80 -""
'"
Q)
a.
39
60 Q)
No significant UV
<II
'"
40 '0
0
20
I
40 80 120 160 200 240 280

role
13e NMR Spectrum

(20.0 MHz. CDC'3 solution)
,......
.ljJ 1
off-resonance decoupled -I"
TMS
/ solvent
i
/
III
proton decoupled
200 160 120 80 40 o 0 (ppm)
11
1H NMR Spectrum
(100 MHz, CDCI 3 solution) 25 Hz
I I
I

i I
I
6.27 4.90 4.25 2.55 ppm
J J-
.:
J TMS
i I I I
A I
j
I I I
U
I I
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
362
Problem 273
IR Spectrum
(KBr disc) 1697
4000 3000 2000 1600 1200 800

V (crn")

80 .>It.
'Co"
Ql
Amax 334 nm (109101': 3.2)
60 Ql
''""
.0 154 Amax 279 nm (109101': 3.7)
40 15 M+" = 216 1%)
cf!.. 198 Amax 270 nm (109101': 3.7)
20
C 12H 804 Amax 236 nm (109101': 4.8)
solvent: methanol
40 80 120 160 200 240 280
m/e
13C NMR Spectrum

(50.0 MHz. CDCliCD3S0CD3 solution) expansion
'-J
solvent
.--' \.J V "---

I I
proton decoupled 132.5 130 ppm
I I I I I , I I I I I I
200 160 120 80 40 o s (ppm)
1H NMR Spectrum
12 11 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
() (ppm)
363
Problem 274a
/
A 400 MHz 1H NMR spectrum (with expansions

and decouplings) is given on the following page
IR Spectrum
(CHCI 3 solution)
4000 3000 2000 1600 1200 800 0.0

V (crn")

80 -"
03
CIl
Cl.
60 Q)
l/l M+' UV spectrum
03
.D 203 1.0 0.224 mg /10 mls
40 '0 path length: 0.5 cm
;,'<
20 solvent: ethanol
__L..........J ....L... __L... ....L... __L... 1.5 u.... ......u

40 80 120 160 200 240 280 200 250 300 350
m/e A. (nm)
13C NMR Spectrum 12 lines

(20.0 MHz, CD 3SOCD3 solution)
2 resonances TMS
solvent
/
proton decoupled
I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
(100 MHz, CD 3SOCD3 solution)
50 Hz 3H
TMS
I
7.0 ppm
2H 1H
10 9 8 7 6 5 4 3 2 1 o
o(ppm)
364
Problem 274b
1H NMR Spectrum 1H
1H
Aromatic region only
1H
1H 1H 1H
Note: Irradiation of the signal at II 4.05 in the

1H NMR produces an enhancement of the
signals at II 7.00 and 8.29 ppm via the NOE
8.6 8.2 -7.8 7.4 7.0

o (ppm)
Expansion of regions
of the 400 MHz NMR spectrum
20.0 Hz
8.631 ppm 8.291 ppm
7.760 ppm 8.353 ppm 7.612 ppm 7.002 ppm
365
Problem 275
1H NMR Spectrum
I--
0---
r-r--
-
,
I
, ,
r-r- I I I i
TMS
8.0 7.6 ppm
I
----1
I
-II I I I I
-
I
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
366
Problem 276
"\
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800

V (crn'")

M+' \I
80 -" 141 156
'"
a>
Q. Amax 321 nm (10910 2.6)
60 a>
Amax 281 nm
V)
'"
.a (10910 3.7)
40 '0
o '. solvent: ethanol
20
40 80 120 160 200 240 280

m/e
I I I I I I I I I I I ,
NMR Spectrum

13C
I I I
130 125 ppm
DEPT CH2 ' CH 3t CHt
Resolves into

--- I I
130
I
125 ppm
proton decoupled
I solvent I
200 160 120 80 40 o 0 (ppm)
1H NMR Spectrum
expansion
I
8.0 7.0 ppm
TMS
10 9 8 7 6 5 4 3 2 1 o
o (ppm)
367
Problem 277
IR Spectrum
(KBr disc)
4000 3000 2000 1600 1200 800

V (cm")

127 M+'
80
162/164
III
Q)
0- Amax 311 nm (10910c 2.6)
60 Q)
Amax 289 nm
l/l
III
.0 ( 10910 c 3.7)
40 '0
*- Amax 225 nm (10 9101'; 5.0)
20
I. Ll solvent: methanol
40 80 120 160 200 240 280 /' .
m/e
13C NMR Spectrum

expansion
I ,
I
135 125 ppm
DEPT 1 CHJ

CH 2 CHt
expansion
/ solvent
,
I
/ I I I
proton decoupled
II 135 125 ppm
200 160 120 80 40 o 8 (ppm)
1H NMR Spectrum
expansion
at 600 MHz
TMS
I I
7.8 7.6 7.4 ppm
10 9 8 7 6 5 4 3 2 1 o
8 (ppm)
368

Spectroscopy Practice Problems

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Spectroscopy Practice Problems

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Problem 1

4000 3000 2000 1600 1200 800 0.0

40 80 120 160 200 240 280 200 250 300 350

13C NMR Spectrum

200 160 120 80 40 o 0 (ppm)

4000 3000 2000 1600 1200 800

100 Mass Spectrum

13C NMR Spectrum

4000 3000 2000 1600 1200 800 0.0

100 Mass Spectrum

13C NMR Spectrum

DEPT CH 2 t

proton decoupled solvent

4000 3000 2000 1600 1200 800

DEPT CH2 t CHat CHt

proton decoupled solvent

200 160 120 80 40 o 0 (ppm)

4000 3000 2000 1600 1200 800

100 Mass Spectrum

.11 ,I, C2 H4 Br2

40 80 120 160 200 240 280

13C NMR Spectrum

4000 3000 2000 1600 1200 800

100 Mass Spectrum UV Spectrum

40 80 120 160 200 240 280

13C NMR Spectrum

200 160 120 80 40 o s (ppm)

4000 3000 2000 1600 1200 800

100 Mass Spectrum

13C NMR Spectrum

4000 3000 2000 1600 1200 800

100 Mass Spectrum

40 80 120 160 200 240 280

proton decoupled solvent

200 160 120 80 40 o 0 (ppm)

4000 3000 2000 1600 1200 800

100 Mass Spectrum

13C NMR Spectrum

200 160 120 80 40 0 S (ppm)

4000 3000 2000 1600 1200 800

100 56 Mass Spectrum

40 80 120 160 200 240 280

13e NMR Spectrum

200 160 120 80 40 o 0 (ppm)

4000 3000 2000 1600 1200 800

100 Mass Spectrum

40 80 120 160 200 240 280

13C NMR Spectrum

200 160 120

1H NMR Spectrum expansion

2.2 1.8 PPM TMS

4000 3000 2000 1600 1200 800 0.0

Mass Spectrum 0.5

13C NMR Spectrum No TMS in

4000 3000 2000 1600 1200 800

100 63 Mass Spectrum

13C NMR Spectrum

200 160 120 80 40 0 " (ppm)

6.0 5.8 ppm 2.2 2.0 ppm

4000 3000 2000 1600 1200 800

100 45 Mass Spectrum

40 80 120 160 200 240 280

200 160 120 80 40 o 0 (ppm)