CHEM 221

Brown Chapter 3

Answers to problems in the coursepack

3.12 a) CHCl3 only one isomer; CH2Cl2 only one isomer; CHClBrF two isomers

b) CHCl3 only one isomer; CH2Cl2 two isomers cis and trans

CHFClBr three isomers

3.13 a) yes C-2 is a stereogenic center b) no, it is symmetrical c) yes C-3 is a stereogenic center d) yes C-2
is a stereogenic center
3.14 a) CH3CH2CH(CH3)CH2CH2CH3 this is the smallest acyclic alkane with a chiral center on C-3. There is a
smaller cycloalkane with a chiral center, trans-1,2-dimethylcyclobutane
b) CH3CH(OH)CH2CH3 c) CH3CH2CH(CH3)C=0 d) CH3CH2CH(CH3)C=0CH3 e) CH3CH2CH(CH3)CO2H f)
CH3CH2CH(CH3)CO2CH3

3.15 a)

e)

b)

f)

c)

g)

3.16 They are all identical stereorepresentations

d)

h)

CHEM 221

3.17 a) no stereocenter b)

Brown Chapter 3

Answers to problems in the coursepack

it has two stereoisomers c)

it has two stereoisomers d) no stereocenter e) no

stereocenter f)

two stereocenters

g) no stereocenter
3.19 a) OH (1), -CH2OH (2), -CH3 (3) and H (4) b) CH=CH2 (1), -CH2CO2H (2), CH2CH=CH2 (3) and CH3 (4)
c) NH3+(1), CO2- (2), CH3(3) and H (4) d) NH3+(1), -CH2SH (2), CHO (3) and CH3 (4)
3.20 (-)-carvone is R and (=)-carvone is S

CHEM 221

Brown Chapter 3

3.21a) S-2-butanol b)

Answers to problems in the coursepack

c)

The last one is more stable. It is similar in stability compared with the
conformer shown in b). Both have only one gauche interaction whereas the first one drawn in c) has two
gauche interactions.

3.22

3.24
are identical and they are called meso

3.23 S OH (1), -14CH2(2), -COOH (3) and CH2 (4)

These two stereorepresentations

CHEM 221

Brown Chapter 3

Answers to problems in the coursepack

These two stereorepresentations are

enantiomers one of another.

3.25 a)

b)

c)

d)

4 stereoisomers possible

4 stereoisomers possible

4 stereoisomers possible

2 stereoisomers possible

CHEM 221

e)

f)

g)

h)

Brown Chapter 3

Answers to problems in the coursepack

8 stereoisomers possible

2 stereoisomers possible

4 stereoisomers possible

4 stereoisomers possible

CHEM 221

Brown Chapter 3

3.26
stereoisomers, but some are geometrically impossible!

Answers to problems in the coursepack

Theoretically, 64

3.27
3.29 a) enantiomers b) diastereoisomers c) diastereoisomers
3.30 a), c), d), f) and h) are meso compounds because they have an internal plane of reflection.