Chem 31

FS AY 2019-2020

Problem Set II

1. Draw the structures and name the four constitutional isomers with molecular formula C 4H9 Br.

2. Draw the structure of each of the following compounds:

a. 2,3-dimethylhexane d. 2,2-dimethyl-4-propyloctane
b. 4-isopropyl-2,4,5-trimethylheptane e. 4-isobutyl-2,5-dimethyloctane
c. 4,4-diethyldecane f. 4-(1,1-dimethylethyl)octane

3. Give the systematic name for each of the following compounds:

a. d.

b.

e.

c.

f.

g.

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4. Give the systematic name for each of the following compounds:
CH2CH3

CH

a. c. CH2CH2CH3

CH2CH3

b. d.

5. Using Newman projections, draw the most stable conformer for the following:

a. 3-methylhexane, considering rotation about the C3-C4 bond.

b. 3,3-dimethylhexane, considering rotation about the C3-C4 bond.

6. Which will have a higher percentage of the diequatorial-substituted conformer, compared with the
diaxial-substituted conformer: trans-1,4-dimethylcyclohexane or cis-1-tert-butyl-3-methylcyclohexane?

trans-1,4-dimethylcyclohexane cis-1-tert-butyl-3-methylcyclohexane

7. Determine whether each of the following compounds is a cis isomer or a trans isomer:
H H H H
a. b. c. H

Cl Br CH3
Br CH3
Br
H

Br H H
CH3
d. e. f.
H3C H Cl CH3
CH3
H
H H

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8. Draw the cis and trans isomers for the following compounds:

a. 1-bromo-4-chlorocyclohexane

b. 1,3-dibromocyclobutane

9. Draw all possible stereoisomers for each of the following compounds. State if no stereoisomers are
possible.

a. 1-bromo-2-chlorocyclohexane

b. 1,2-dichlorocyclohexane

c. 3,3-dimethylpentane

d. 1-bromo-3-chlorocyclobutane

10. Name each of the following compounds using R,S designations where necessary:

CH3
CH2OH
HO H
a. HO CH3 b.
H Cl
CH2CH2CH2OH
CH2CH3

11. Mevacor® is used clinically to lower serum cholesterol levels. How many asymmetric carbons does
Mevacor® have?
HO O

O
O

Mevacor

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12. Indicate whether each of the following pairs of compounds are identical or are enantiomers,
diastereomers, or constitutional isomers:

CH3 CH2CH3

H Cl and H H
HO H HO H
a. d. and
H Cl H Cl

H Cl Cl Cl
CH2CH3 CH3

b. e. H3C CH3
H CH3
Cl H and H Cl

and
H3C Br H Br
H Cl Cl H

CH2CH3
H Br H H

c. and f. and

Br H Br Br

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