CHEMISTRY 2411 NAME_________________

EXAM IIIA - Key

Fall, 2012
Kirberger

All notes, books, etc., must be placed out of sight. Please read each of the problems carefully. If
something is not clear, please ask.

The exam is worth a total of 112 points. Make sure your exam is complete.

Answers should be placed in the space provided. Write legibly--if I cannot read it--it is wrong.
Please include an explanation whenever asked to or whenever necessary to make your answer
clear. Please put your name on every page of the exam.

As usual, no cheating is allowed. Good Luck!!!

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1) (8 Points) Name each of the following compounds.

a. 3,6-dibromo-4-methyl-5-propylnonane

Br

Br

b. 2-bromo-9-chloro-5,6-diisobutyl-1,10-difluorodecane

Cl
F
F
Br

2) (8 Points) Draw each of the following compounds using skeletal structures.

a. trans-1,2-dichlorocyclopentane b. (2R,3S)-2-chloro-3-methylpentane
Cl

Cl
H
H3C CH3
H3C
Cl H
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3) (4 Points) What term describes the structural relationship between (2R,3R,4S)-2,3,4-

trichloroheptane and (2S,3S,5R)-2,3,5-trichloroheptane?

A) not isomers
B) constitutional isomers
C) enantiomers
D) diastereomers
E) conformers

Answer: B

4) (4 Points) Which of the following incorrectly describes cis-1,2-dimethylcyclopentane?

A) It is a meso compound.
B) It is achiral.
C) It contains two asymmetric carbons.
D) Its diastereomer is trans-1,2-dimethylcyclopentane.
E) It has an enantiomer.

Answer: E

5) (4 Points) Is the molecule shown below chiral or achiral?

Answer: achiral

6) (4 Points) How many asymmetric carbons are present in the compound below?

Answer: 5
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7) (20 Points) Draw all of the possible stereoisomers of the following compound. Indicate
whether the drawn structure is an enantiomer or a diastereomer of the original structure.

H O

H OH

HO H

H OH

HO

8) (4 Points) For the structure shown below, draw the stereoisomer having a configuration of
(1R,3S,4S) in a perspective structure.

H
HO
H

9) (4 Points) Would a 50:50 mixture of (2R,3R)-2,3-dibromobutane and (2R,3S)-2,3-

dibromobutane be optically active? Explain.

Answer: Yes, the mixture would be optically active. This is not a racemic mixture but a mixture
of diastereomers. The specific rotations of diastereomers are not the same in magnitude nor
necessarily opposite in sign.
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10) (4 Points) Draw the Fischer projection of (2R,4R)-2,4-dibromopentane.

Answer:

11) (4 Points) Is it theoretically possible to separate the pair of compounds below by distillation?
Explain briefly.

Answer: Yes. The molecules are related as diastereomers and hence have different boiling points.

12) (4 Points) Which of the following is a geminal dihalide?

A) cis-1,2-dibromocyclopentane
B) 3,3-dichloropentane
C) trans-1,4-diiodocyclohexane
D) isobutyl chloride
E) 1,3-dibromoheptane

Answer: B

13) (4 Points) Which halide is a better nucleophile, iodide or fluoride? Explain.

Answer: The iodide ion is the better nucleophile. The larger size of this ion renders its electron
cloud more polarizable.
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14) (4 Points) What type of solvent is best for SN2 reactions which employ anionic nucleophiles:
polar, protic solvents; polar, aprotic solvents; or nonpolar solvents? Explain.

Answer: Polar, aprotic solvents are best. These solvents have strong dipole moments to enhance
solubility of the anionic species but lack the ability to solvate the anion by hydrogen bonding.

15) (4 Points) Arrange the following substrates in order of their increasing SN2 reactivity with
NaCN: bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-
bromo-2-methylpentane.

Answer: 2-bromo-2-methylpentane < 1-chloro-2,2-dimethylpentane < 1-chloro-3,3-

dimethylpentane < bromoethane

16) (4 Points) Which of the following statements describe a favorable attribute of a leaving
group? (More than one answer is possible.)

A) The leaving group should be highly polarizable.

B) The lower the electronegativity of the leaving group the better.
C) Good leaving groups need to have low steric hindrance.
D) The departed leaving group should have low basicity.

Answer: A, D

17) (12 Points) Complete the following reactions. Reactions may undergo more than 1 type of
reaction (SN1, SN2, E1 or E2) and thus generate multiple products.

a.

O
O
+ CH3CH2OH + +
Br
E1 SN1 SN1

b.
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+
O
SN1
O
+ OH
Br

c.

H
DMF
+ KCN SN2
I H N

18) (4 Points) Draw the structures of the E2 products that would be observed with the following
reaction. Indicate which product is the major product, and explain why it is the major product.

NaOCH3 +
HOCH3 minor major
Br

19) (4 Points) Draw the structure of the major E1 product that would be observed with the
following reaction.

+ HOCH3
Br

20) (4 Points) Why do E1 and SN1 reactions frequently occur together?

Answer: Due to formation of carbocation as the first step.