Page 1
1.
What would be the name of the following compound?
CH3
CH3
H
A)
2,3-dimethylcyclopentene
B)
(R)-1,5-dimethylcyclopentene
C)
cis-2,3-dimethylcyclopentene
D)
cis-1,5-dimethylcyclopentene
E)
trans-2,3-dimethylcyclopentene
2.
Which of the following alkenes of the formula C5H10 would you expect to be the least
stable?
A)
B)
C)
D)
E)
Page 2
3.
What would be the organic product of the following reaction?
C C
Ph Br
H3C
H3C
Ph
H
CH3O– Na+
?
A)
B)
C)
C C H
PhH3C
Ph
D)
CC
H3C
Ph Ph
CH3
E)
none of the above
4.
What would be the proper name of the following?
C C H
CH3
CH2
CH3
Cl
A)
(Z)-3-chloro-2-pentene
B)
(Z)-3-chloro-3-pentene
C)
(E)-3-chloro-2-pentene
D)
(E)-3-chloro-3-pentene
E)
cis-3-chloro-3-pentene
5.
Infrared spectroscopy relies on what phenomenon?
A)
electronic transitions
B)
molecular rotations
C)
nuclear alignments
D)
molecular stretching and bending
E)
conformational interconversion
Page 3
6.
The IR spectrum of a compound shows a strong absorbance peak at 1720 cm–1. What
functional group is indicated?
A)
OH
B)
C=C
C)
NH
D)
C=O
E)
CN
7.
A hydrocarbon with the molecular formula C7H12 exhibits the following spectroscopic
data: 1H NMR = 1.3 (m, 2H), 1.7 (m, 4 H), 2.2 (m, 4H), and 4.8 (quin, J = 3 Hz,
2H) ppm; 13C NMR: = 26.8, 28.7, 35.7, 106.9, and 149.7 ppm. The IR spectrum
has key absorbances at 3072, 2950, and 1649 cm–1. Hydrogenation of the compound
furnishes a product with the molecular formula C7H14. Which structure is consistent
with this data?
A)
B)
C)
D)
E)
None of the above.
8.
How many units of unsaturation are indicated by the following molecular formula:
C17H18BrI2O2N ?
A)
0
B)
2
C)
6
D)
8
E)
10
Page 4
9.
The following molecule contains how many units of unsaturation?
HO
O
A)
2
B)
3
C)
5
D)
6
E)
7
10.
Predict the major product of the following reaction:
H2 / Pd–C ?
heat
A)
O
B)
C)
D)
Pd
H
H
E)
None of the above.
11.
Which of the following most accurately describes the IR fingerprint region:
A)
2200 – 3400 cm–1
B)
600 – 1500 cm–1
C)
3000 – 3500 cm–1
D)
1500 – 1850 cm–1
E)
600 – 950 cm–1
Page 5
12.
Which of the following are of lowest energy?
A)
radio waves
B)
x-rays
C)
infrared
D)
ultraviolet
E)
microwaves
13.
The following molecule contains how many units of unsaturation?
O
A)
1
B)
2
C)
3
D)
4
E)
5
14.
What functional group would be indicated by an IR absorption at 2150 cm–1?
A)
C=O
B)
C=C
C)
OH
D)
NH
E)
CC
15.
What functional group would be indicated by an IR absorption at 1650 cm–1?
A)
C=O
B)
C=C
C)
OH
D)
NH
E)
CC
Page 6
16.
Under special reaction conditions, -pinene and -pinene can be in equilibrium (caused
to interconvert reversibly). Using your knowledge of alkene stability, which of the
following would be true at equilibrium?
CH3CH2
–pinene –pinene
A)
The -isomer will predominate.
B)
The -isomer will predominate.
C)
The isomers would be equally favored.
D)
A third isomer would predominate.
E)
None of the above is true.
17.
The greatest strength of infrared spectroscopy is in determining
A)
the degree of unsaturation.
B)
the relationships of structural fragments.
C)
the functional groups present.
D)
the overall structure of the molecule.
E)
if rings are present.
18.
How many degrees of unsaturation are present in the following molecule?
C14
H13
F3N2O
A)
3
B)
5
C)
7
D)
8
E)
10
Page 7
19.
The following molecule contains how many units of unsaturation?
O
A)
7
B)
9
C)
10
D)
11
E)
15
20.
Which of the following are (Z) isomers?
H3C
Cl
Br
CH3
H3C
H
CO2H
CH3
H
H3C
CHO
CO2H
H3C
C6H5
CO2H
H
H
H3C
N(CH3)2
CH3
54
321
A)
1 and 5
B)
2 and 5
C)
3 and 5
D)
2 and 3
E)
2, 4 and 5
Page 8
21.
Predict the product of the following reaction:
Ph
Br Et
H
Me
Na+ –OMe ?
A)
Ph
MeO Et
HMe
B)
Ph Me
Et
C)
Ph
Et OMe
HMe
D)
Et Me
Ph
E)
Ph OMe
Et
22.
Which of the following are of highest energy?
A)
radio waves
B)
X-rays
C)
infrared
D)
ultraviolet
E)
microwaves
Page 9
23.
Which is the structure of 3,7-dimethyl-2,6-octadienal?
A)
CH2OH
CH3
B)
CHO
CH3
C)
CHO
CH3
D)
CHO
CH3
E)
CH2OH
Page 10
24.
Which structure would be named 3-bromo-5-methylcyclohexene?
A)
Br
CH3
B)
Br
CH3
C)
Br
CH3
D)
CH3
Br
E)
None of the above.
25.
Which of the following are (E) isomers?
H3C
Cl
Br
CH3
H3C
H
CO2H
CH3
H
H3C
CHO
CO2H
H3C
C6H5
CO2H
H
H
H3C
N(CH3)2
CH3
54
321
A)
1, 3, and 5
B)
2, 4, and 5
C)
1, 4, and 5
D)
1, 2, and 4
E)
2, 3, and 4
Page 11
26.
Which of the alkenes shown below would be expected to have the lowest melting point?
A)
B)
C)
D)
E)
There is no basis for such a prediction.
27.
What reagent would give the highest yield of the product shown below?
Br
?
A)
K+-OtBu
B)
NaCN
C)
CH3S–Na+
D)
NaOH
E)
CH3O–Na+
28.
If you could have only one of the following to use to identify the entire structure of a
previously unknown organic compound, which would be the best?
A)
melting point
B)
IR spectrum
C)
molecular weight
D)
NMR spectrum
E)
boiling point
29.
Which reagent(s) would you expect to give the highest yield of the product shown?
Br
A)
K+-OtBu
B)
CH3S– Na+
C)
H2SO4
D)
CH3O– Na+
E)
K+ –CN
Page 12
30.
Which alkene would you expect to release the least amount of heat upon
hydrogenation?
A)
B)
C)
D)
E)
31.
Which sets of arrows correctly represents the electron movements during an E2
reaction?
A)
C C
Br
H
HO
B)
C C
Br
H
HO
C)
C C
Br
H
HO
D)
C C
Br
H
HO
E)
C C
Br
H
HO
Page 13
32.
Based on what you know about carbon-carbon double bonds, which of the following
would be true of the allene shown?
C C C
an allene
A)
The two rings would be in the same plane.
B)
The two rings would be in perpendicular planes.
C)
There is no way to tell what geometric relationship the rings would have.
D)
The three carbons shown would not be co-linear.
E)
Allenes cannot exist.
33.
Which of the following are E isomers?
CH3
H
CH3
Br
Cl
Br
Cl
HCH3
H3C
III III
IV V
A)
III and V
B)
II and IV
C)
I, III, and V
D)
II and III
E)
I, II, and IV
Page 14
34.
What product would you expect from the reaction shown below?
CH3Br CH3O– Na
+
CH3OH ?
A)
CH2
B)
CH3
OCH3
C)
CH3
D)
CH3
E)
CH3
35.
Which is the correct order of stabilities of alkenes listed from least stable to most stable?
A)
C C
R
R
R
R
C C
R
H
R
H
H2C CH2<<
B)
C C
R
H
R
H
C C
R
R
R
R
H2C CH2
<<
C)
C C
R
H
R
H
C C
R
R
R
R
H2C CH2<
<
D)
C C
R
R
R
R
H2C CH2
C C
R
H
R
H
<
<
E)
C C
R
R
R
R
H2C CH2C C
R
H
R
H
<<
Page 15
36.
What would be the MAJOR organic product of the following reaction?
HO H2SO4/heat
A)
B)
C)
D)
OH
SO4
E)
37.
A chiral compound, C5H8, upon simple catalytic hydrogenation yields an achiral
compound. What is the best name for the former?
A)
1-methylcyclobutene
B)
3-methylcyclobutene
C)
1,2-dimethylcyclopropene
D)
cyclopentene
E)
None of the above.
38.
What is the degree of unsaturation in cyclobutene
A)
zero
B)
one
C)
two
D)
three
E)
This molecule is not unsaturated.
39.
Choose the name of the following compound.
A)
cis-4,5-dimethylcyclopentene
B)
cis-1,2-dimethylcyclopent-3-ene
C)
cis-2,3-dimethycyclopentene
D)
cis-3,4-dimethylcyclopentene
E)
cis-1,2-dimethylcyclopent-4-ene
Page 16
40.
A compound which shows a molecular ion at m/z 84 could plausibly have what
formula?
A)
C5H10N
B)
C4H20O
C)
C6H12
D)
C5H24
E)
C5H10O
41.
Enanthotoxin is an extremely poisonous organic compound found in the hemlock water
dropwart, which is reputed to be the most poisonous plant in England. It is believed that
no British plant has been responsible for more fatal accidents. The most poisonous part
of the plant is the roots, which resemble small white carrots, giving the plant the name
“five finger death.” Also poisonous are its leaves, which look like parsley. Enanthotoxin
is thought to interfere with the sodium ion current in nerve cells which leads to
convulsions and death. How many stereoisomers are possible for enanthotoxin?
OH
OH
A)
2
B)
4
C)
8
D)
16
E)
32
42.
Label each of the alkenes as either E or Z.
O
CH2CH3
SiCH3H3CCH3FCl
ABCD
Br
OCH3
H3C
A)
A = E, B = Z, C = E, D = Z
B)
A = Z, B = E, C = Z, D = E
C)
A = Z, B = E, C = Z, D = Z
D)
A = E, B = E, C = E, D = E
E)
None of the above.
Page 17
43.
How many degrees of unsaturation are present in the following molecule?
A)
4
B)
5
C)
6
D)
7
E)
8
44.
The mass spectrum of 1-pentanol gives a large peak at m/z = 70. This peak can be
characterized as?
A)
the parent ion
B)
the parent ion minus hydroxide
C)
the parent ion minus water
D)
the parent ion plus a proton
E)
None of the above.
45.
The mass spectrum of isopropylbenzene gives a large peak at m/z = 105. This peak can
be characterized as?
A)
the parent ion
B)
the parent ion minus a proton
C)
the parent ion minus water
D)
the parent ion minus a methyl group
E)
None of the above.
Page 18
46.
What would be the major product of the following reaction?
CH3CH2CH CH3
Br
?
KOH
heat
A)
H3C
C C
CH3
H
H
B)
CH3CH2CH CH3
OH
C)
H3C
C C
CH3
HH
D)
CH3CH2CH CH2
E)
CH3CH2CCH3
O
47.
Predict the product of the following reaction.
Br
H
Ph
H3C
H
Ph (i-Pr)2NH
A)
N(i-Pr)2
H
Ph
H3C
H
Ph
B)
H
Ph
N(i-Pr)2
H3C
H
Ph
C)
H
Ph
H3C
Ph
D)
Ph
H
H3C
Ph
E)
no reaction
Page 19
Answer Key
Page 20