CHEM 130
Fall 2004
PRACTICE EXAM 2
Chapters 4-7
Multiple Choice.
1. ______ What is the correct IUPAC name of the following
compound?
a) trans-2-ethyl-6-propyl-3-octene
b) trans-3-methyl-7-propyl-4-nonene
c) trans-7-ethyl-3-methyl-4-decene
d) cis-7-ethyl-3-methyl-4-decene
2. ______ What is the correct structure for 1,5-dimethylcyclohexene?
a
b
c
d
3. ______ What is the correct stereochemical designation for the following molecule?
a)
b)
c)
d)
cis
trans
E
Z
Cl
Br
4. ______ What is the correct stereochemical designation for the following molecule?
a) cis
O
b) trans
c) E
d) Z
OH
True or False
Consider the following reaction to answer the following True/False questions.
HBr
Br
Br
a
b
5. ______ The reaction produces a 50/50 mixture of a and b.
(True or False)
6. ______ The products a and b are enantiomers.
(True or False)
7. ______ Product b is a meso compound.
(True or False)
True or False Consider the following reaction of HCl with 3-methyl-1-butene and the
corresponding reaction energy diagram to answer the following questions.
b
d
E
c
a
e
reaction progress
8. ______
Point c on the reaction energy diagram above represents the carbocation
intermediate for this reaction.
9. ______
The intermediate for this reaction is a secondary (20) carbocation.
10. ______
Point b on the reaction energy diagram represents the transition state for
the second step of the reaction.
11. ______
The rate for the fist step is greater (faster) than the rate of the second step
of the reaction.
True or False Consider the two following reactions (a & b) to answer the following
True/False questions.
-
HS
a
Br
SH
-
HS
b
Br
SH
12. ______ The rate of reaction b is greater than the rate of reaction a.
13. ______ The rates of reaction b is dependent upon the concentrations of the alkyl
halide and HS-.
14. ______ Both reactions a and b are SN1 reactions.
Multiple Choice.
product.
For the following
reaction problems, predict the correct
15. ______
Br
HBr
Br
Br
Br
a
b
c
OH
OH
d
16. ______
OH
H2 O, H+
OH
OH
a
b
d
c
17. ______
Br
CH3
Br
Br
Br
Br
Br2
CH3
a
b
Br
CH3
Br
c
CH3
d
18. ______
H2 , Pd
a
b
c
d
Multiple Choice.
19.) ______ Identify the chiral centers in
Penicillin V.
a) a & b & c & d & e
b) a & c
c) b & d & e
d) a & b & d
O
H
N
e
a
O
O
d
S
c
N
b
CO2 H
Penicillin V
20.) ______ What is the correct configurational assignment for the following compound?
a) R
OH
b) S
CH3
c) E
H
d) Z
21.) ______ What is the relationship between the following compounds?
a) enantiomers
OH
HO
b) diastereomers
c) identical
d) meso
OH
HO
22.) ______ Which of the following compounds are optically active? (Remember to
consider planes of symmetry)
a) a & b & c & d
CH3
CH3
b) a & b
Br
H
HO
HO
c) b & c
H
Br
H
H
d) c & d
Br
Br
CH3
CH3
a
b
HO
HO
c
23.) ______ What are the stereochemical configurations of the two diastereomers of
(2S,4R)-dibromoctane?
a) (2S,4R) and (2R,4S)
c) (2S,4S) and (2R,4R)
b) (2S,4S) and (2R,4S)
d) (2S,4S) and (2S,4R)
d
PRACTICE EXAM 2 Answer Key
1. c
2. b
3. d
4. d
5. T
6. T
7. F
8. T
9. T
10. F
11. F
12. F
13. T
14. F
15. c
16. b
17. c
18. a
19. c
20. a
21. b
22. c
23. c