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148 Chapter 3

Copyright © 2017 Pearson Education, Inc.

57.

a.

1.

    2,2,6-trimethylheptane

2.

    5-bromo-2-methyloctane

3.

    5-methyl-3-hexanol

4.

    3,3-diethylpentane

5.

    5-bromo-

N

-ethyl-1-pentanamine

6.

    2,3,5-trimethylhexane

7.

3-ethoxyheptane

8.

1,3-dimethoxypropane

9.

N,N-

dimethylcyclohexanamine

10.

3-ethylcyclohexanol

11.

1-bromo-4-methylcyclohexane

b.

2.

1.

5.

3.

6.

7.

OH

9.

10.

11.

4.

Br

N

H

O

N

OH

Br

O

8.

O

CH

3

CHCH

2

CH

2

CHCH

2

CH

2

CH

3

CH

3

Br

CH

3

CHCH

2

CHCHCH

3

CH

3

CH

3

CH

3

58.

C

and

D

are cis isomers. (Both substituents are downward pointing in

C

; both substituents are upward

pointing in

D

.)

59.

a. 1.

3 

2.

4

b.

1.

6 

2.

5

c. 1.

3 

2.

4

60.

The first conformer (

A

) is the most stable because the three substituents are more spread out, so its gauche

interactions will not be as large. (The Cl in

A

is between a

CH

3

and an H, whereas the Cl in

B

and

C

is

between two

CH

3

groups.)

61.

a.

b.

c.