IR Spectrum

(KBr disc)
1600
Problem 21
4000 3000
2000 1600
V (crn'")
100
80
"" co
Q)
c,
60
Q)
en
co
.c
40 '0
;f!.
20
30
Mass Spectrum
No significant UV
absorption above 220 nm
40 80 120 160
m/e
200 240 280
13C NMR
Spectrum
(100.0 MHz,
O
2
solution)
..........,1.'.' ".OJ : ...,/.".' ......." ....... h, I 4.... t ,cart. WIU"M ,
" ~ .....,
proton decoupled
200
160 120 80 40 0
o(ppm)
1H NMR Spectrum
(400 MHz, 020 solution)
Note: there are 3 protons
H
2
0 and HOD
which exchange with
in solvent
the 020 solvent
..
I
expansions
J
i i
,
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
I
1\
Problem 22
IR Spectrum
(liquid film)
4000 3000 2000 1600 1200 800
V (ern")
100 Mass Spectrum
M+' 108
80
.:.:
ell
<Il
Cl.
78
60
<Il
Vl
ell
.0
40 '0
<fi.
j j,
93
20
l
C
7Ha
O
40 80 120 160 200 240 280
m/e
UV Spectrum
A
max
269 nm (I091QE 3.2)
solvent: methanol
13C NMR Spectrum
(100 MHz, CDCI
3
solution)
proton decoupled
200
1H NMR Spectrum
(400 MHz, CDCI
3
solution)
expansion
160
lJJ
W
solvent

120 80 40 0
o(ppm)
10
i i
7.2 7.0
9 8 7 6 5 4 3 2 1
TMS
o
o(ppm)
III
IR Spectrum
(liquid film)
Problem 23
91
UV Spectrum
A
max
243 nm (10910 1.9)
A
max
248 nm (10910 2.1)
A
max
252 nm (10910 2.2)
Amax 258 nm (10910 2.3)
Amax 264 nm (10910 2.1)
A
max
268nm (10910 1.9)
solvent: ethanol
800
Mass Spectrum
240 280
1200
200 120 160
m/e
2000 1600
V (crn'")
80
79
3000
40
4000
100
80
""
'"
<Il
0.
60
<Il
en
'"
J:J
40 15
*-
20
I I
129 128 127 ppm
13C NMR Spectrum
(100 MHz, CDCI
3
solution)
solvent
proton decoupled
I I I I
129 128 127 ppm
200 160 120 80 40
o 0 (ppm)
1H NMR Spectrum
(400 MHz. CDCI
3
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
0.5 91
II)
o
80 -"
c:
11l
11l
II)

a.
0
60
II)
'"
'"
.Cl
11l
11l
.Cl
1.0
40 '0
'#
20
I ,\, .n
M+'
170/172
C
7H 7Br
1.5
40 80 120 160 200 240 280
200
mle
UV spectrum
0.917 mg 110 mls
path length: 0.20 cm
solvent: hexane
250 300 350
A. (nm)
I I I
13C NMR Spectrum
(50.0 MHz, CDCI
3
solution)
proton decoupled
I I
200
I
I
I
160
I I
~
expansion
I i
140 130
expansion
~
I i
140 130
solvent

I I I I
120 80
I
ppm
I
ppm
40
I I
I
o s (ppm)
1H NMR Spectrum
(200 MHz, CDCI
3
solution)
r-
~
TMS
t I
I I I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
() (ppm)
113
r
2251
IR Spectrum
(liquid film)
Problem 25
3000 4000 2000 1600
V (ern")
1200 800
100
80
.><
'"
'" 0-
60
'"
'"
'"
.0
40 '0
~
20
77
M+" =117
Mass Spectrum
40 80 120 160
m/e
200 240 280
I I I
I
I I I I r T T I
13C NMR Spectrum
expansion
(100.0 MHz, CDCI
3
solution) ~
i i i
130 129 ppm
DEPT
CH
z'
CH
3t
CHt expansion
I
~
do
i i
I
proton decoupled
129 ppm
I
solvent

I I I I I I I I I I I I
200 160 120 80 40 0
s (ppm)
1H NMR Spectrum
(400 MHz, CDCI
3
solution)
I---
TMS
-
1
J I I I I I I I I
I
10 9 8 7 6 5 4 3 2 1
0
s (ppm)
114
I I I I I I I I I I I I
13C NMR Spectrum

(100 MHz, CDCI
3
solution)
1 I
DEPT CH21CHJ CHt
129 128 127 ppm
I

solvent
proton decoupled
I
1 I 1
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
Mass Spectrum
UV Spectrum
M+" 107
A
max
256 nm 2.2)
Amax 264 nm 2.1)
solvent: ethanol
J
91
"
J .1.
C
7H
g
N
40 80 120 160 200 240 280
role
4000
100
80
""
lIJ
Ql
c-
60
Ql
'" lIJ

40
'0
oF-
-J,
20
3290
3000
IR Spectrum
(liquid film)
2000 1600
V (cm'")
1200 800
Problem 26
TMS
7.6
10
7.4
9
7.2 ppm
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.
92
60
Q)
1I)
<lI
UV spectrum
.0
1.0
40 '0
M+'= 122
5.662 mg I 10 mls
;f?
20
I, J ,I
I
path length: 1.00 cm
C
aH100
solvent: ethanol
1.5
40 80 120 160 200 240 280 200 250 300 350
m/e A(nm)
I I I
li-
13C NMR Spectrum
expansion
(100.0 MHz, i
, ,
I
CDCI
3
solution)
135 130 ppm
DEPT CH2 f CH
3t
CHt
I
!
'::lL
, , , solvent
135 130 ppm
f
proton decoupled
I I
, ,
I I I
,
I I
-,
200
lH NMR Spectrum
(400 MHz, CDCI
3
solution)
expansion
7.3 7.2 ppm
160 120
expansion
I
3.9 3.8 ppm
80 40 0
() (ppm)
expansion
~ .
2.9 2.8 ppm
Exchanges
with D20
TMS

10
116
9 8 7 6 5 4 3 2 1
o
s (ppm)
3325
IR Spectrum
(liquid film)
Problem 28
104 Mass Spectrum
.><
III
III
Co
Ql
77 78
Ul
III
107 .Q
79
'0
<fi.
.1 j I.
M+'= 122
.1. .1
C
8
H
10O
2000 1600
V (crn")
350
UV spectrum
5.815 mg/10mls
path length: 1.00 cm
solvent: ethanol
250 300
A. (nm)
0.0
1.5 u...................."'-o..J.................. ...L...".................l..o..I...I
200
1.0
0.5 8
c

o
Ul
.Q
III
800
280 240
1200
200 120 160
m/e
80
3000
40
4000
100
80
60
40
20
I I I I I I I I I I I
13C NMR Spectrum
(100.0 MHz, COCI
3
solution)
DEPT CH
2
, CH
3t
CHt
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
7.5 7.3
ppm r-
L
~
TMS
- ' ~
---'
~ ~
I
I
I I I
I I I I I I I
10 9 8 7 6 5 4 3 2 1 o
s (ppm)
117
Problem 29
IR Spectrum
1715
(liquid film)
4000 3000 2000 1600 1200 800
0.0
V (crn")
100
Mass Spectrum
0.5
43
Ql
80 -"
o
c
'"
'"
Ql
e Co
60
Ql 91
0
UV spectrum
UJ
UJ
.J:J
'"
II
'"
.J:J
1.0
solvent: cyclohexane
40 '0
M+'
7.90 mg 110 mls
;ft.
134
path length: 0.50 cm
20
I.
II
,I
C
g
H 1QO
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 I I I
13C NMR Spectrum
(50.0 MHz, CDCI
3
solution)
DEPT CH21CH3t CHt
II I
r
proton decoupled
~
solvent
I ...-J
II
I I I I I I I I I
200 160 120 80 40 0
<5 (ppm)
1H NMR Spectrum
(200 MHz, CDC'3 solution)
~
..-
TMS
~
! 1 ~ L
10
118
9 8 7 6 5 4 3 2 1
o
<5 (ppm)
Problem 30
IR Spectrum
(liquid film)
1690
800
Mass Spectrum
0.5
1200 2000 1600
V (crn'")
105
M+"
1.0
UV spectrum
134
1.075 mg /10 mls
1
path length: 0.10cm
C
g
H 1QO
solvent: ethanol
IJ
1.5
80 120 160 200 240 280 200 250 300 350
m/e A(nm)
77
3000
40
4000
80 ~
Q)
c-
60 ~
'"
.c
40 '0
<;e.
20
100
13e NMR Spectrum
(20.0 MHz, CDCI
3
solution)
off-resonance decoupled
solvent
200 160 120 80 40 0
15 (ppm)
1H NMR Spectrum
(100 MHz, CDC'3 solution)
I
TMS
~ ~ LJ
L
v;
I I I I I I I I I
10 9 8 7 6 5 4 3 2 1 0
15 (ppm)
119