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Test #2
1.
2.
3.
4.
5.
I pledge that I have neither given nor received unauthorized aid on this exam:
_____________________________________
(signature)
Periodic Table
1
1.008
1.008
Li
Be
6.941
9.012
10.81
12.01
14.01
16.00
19.00
11
12
Na Mg
22.99
24.31
19
20
21
22
23
24
13
14
Al
Si
26.98
25
26
27
28
29
30
31
28.09
32
15
16
17
Cl
30.97
32.07
33
34
35.45
35
He 1
4.00
10
Ne 2
2 0.18
20.18
18
Ar 3
39.95
36
Ca
Sc Ti
Cr Mn Fe
Co Ni
Cu Zn Ga Ge
As Se Br
Kr 4
39.10
40.08
44.96
47.87
50.94
52.00
54.94
55.85
58.93
58.69
63.55
65.39
69.72
72.61
74.92
74.92
78.96
79.90
83.80
37
38
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
Zr
Nb Mo Tc Ru Rh Pd Ag Cd
In
Sn Sb Te
Xe
91.22
92.91
95.94
98
01.1
101.1
1
102.9
118.7
121.8
127.6
126.9
131.3
75
76
82
83
84
85
Rb Sr
85.47
87.62
88.91
55
56
57
106.4
72
73
74
77
78
Cs Ba La
Hf
Ta
W Re Os Ir
Pt
132.9
178.5
180.9
87
137.3
138.9
88
89
186.2
190.2
192.2
195.1
112.4
114.8
79
80
81
Au Hg Tl
197.0
200.6
204.4
86
Pb Bi
Po At
Rn 6
207.2
209
222
209.0
210
104
Fr Ra
Ac Rf
(223)
227
226
183.8
107.9
261
58
59
60
61
62
63
64
65
66
67
68
69
70
71
Ce Pr
Nd Pm Sm Eu Gd Tb Dy Ho Er
Tm Yb Lu
140.1
140.9
144.2
90
145
152.0
157.3
158.9
162.5
94
95
96
97
98
164.9
167.3
168.9
173.0
175.0
99
100
101
102
103
91
92
Th Pa
Np Pu Am Cm Bk Cf
Es Fm Md No Lr
232.0
238.0
(237)
(252)
(231)
93
150.4
(242)
(243)
(247)
(247)
(251)
(257)
(258)
(259)
(260)
Test #2
Chem151L Canelas
Summer, 2010
Name:__________________________,_____________________
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Score Summary:
Number
Points
/30
/36
/12
/16
/16
/20
/20
Total
/150
Test #2
Chem151L Canelas
Summer, 2010
1. (30 points)
a) Please used curved arrow notation to write reaction mechanism for the following transformation:
HBr, H2O2,
Br
b) Using the axis below as a guideline, draw the proton NMR spectrum of the major organic
product shown above for the reaction in part a. Please consider the most likely chemical shifts,
multiplicity caused by coupling between protons, and integral values; clearly indicate these on
your drawing.
Test #2
Chem151L Canelas
Last Name: ___________________
Summer, 2010
2. Consider the structures shown in each part and choose the best answer. (36 points)
a) For parts I and II, choose the letter that corresponds to the relationship between each of the pairs listed
below and write it in the answer blank.
B
a) no relationship
b) constitutional isomers
E trans-1,4-dimethylcyclohexane
(most stable chair conformation)
F cis-1-ethyl-2-propylcyclobutane
d) stereoisomers
I) C and D ______
H3C
Br
H3C
H3C
CH2CH3
HO
CH2CH2OH
HO
CH3
Answers:
c) Complete the Fischer projections by drawing the atoms or groups (H or OH) attached to the
horizontal bonds. Then, compare these structures and circle their relationship below.
Compound X:
H
OH
Compound Y:
CH
O
H
O
H
OH
CH
H OH
CH3
HO H
CH3
Constitutional isomers
Enantiomers
Diastereomers
Test #2
Chem151L Canelas
Summer, 2010
H3C
CH3
CH(CH3)2
CH3
b) cis-bicyclo[3.3.0]octane
Test #2
Chem151L Canelas
Summer, 2010
4. For the reactions shown below, draw the structure of the starting material or major organic
product(s), whichever is missing. Please carefully denote configuration of chiral carbons using linewedge-dash notation, if necessary; if a reaction is stereoselective (syn- or anti- addition) and a racemic
mixture results, then please show both products for this exercise. "D" is deuterium, an isotope of
hydrogen that behaves similarly. Reaction mechanisms do NOT need to be shown. (16 points)
a.
Cl2
b.
1. BD3, THF
2. H2O2, OH-
c.
1. O3
2. (CH3)2S
O
H
O
d.
OH
H-O-O-H, hv
HO
Test #2
Chem151L Canelas
Summer, 2010
5. 1,2,3-trifluorocyclopentane has two different meso stereoisomers. Complete the exercises or answer
the questions below. (16 points)
a) Starting with the template below for each, complete the structures by filling in the missing
fluorines and hydrogens for each of the two different meso forms of 1,2,3-trifluorocyclopentane.
(Please note: one fluorine is shown to get you started; please fill in the other 2 F and 3 H atoms
on each line-wedge-dash structure.)
b) On your drawings above, draw an asterisk next to every carbon that is a stereocenter.
c) Pick ONE of the stereocenters youve designated and clearly indicate its absolute configuration (R
or S.) Please make sure you clearly indicate which carbon you have assigned.
d) Would a solution of the compound youve completed on the left rotate plane polarized light? Why
or why not?
e) Circle the relationship between the two structures youve completed in part a.
Identical
Constitutional isomers
Enantiomers
Diastereomers
Test #2
Chem151L Canelas
Summer, 2010
6. Draw the structure of the unknown compound by solving the IR, proton NMR, and mass spectra
provided. Write information about the presence or absence of various functional groups next to
the IR spectrum for full or partial credit. Also, indicate the correlation between the signals on the
NMR and the different protons on your final structure. Please recall that a table of spectral values
is provided as the last page.(20 points)
Functional groups:
Structure of Compound:
Test #2
7.
Chem151L Canelas
Summer, 2010
Draw the structure of the unknown compound by solving the IR, proton NMR, and mass spectra
provided. Write information about the presence or absence of various functional groups next to
the IR spectrum for full or partial credit. Also, indicate the correlation between the signals on the
NMR and the different protons on your final structure. Please recall that a table of spectral values
is provided as the last page.(20 points)
Functional groups:
Structure of Compound:
Test #2
Chem151L Canelas
Summer, 2010
13
C-NMR Spectra