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Chapter 3 157

Copyright © 2017 Pearson Education, Inc.

6.

Draw the other chair conformer for the following compound:

Br

H

CH

3

H

 7.

Which is more stable,

cis

-1-isopropyl-3-methylcyclohexane or

trans

-1-isopropyl-3-methylcyclohexane?

8.

Which of the following has:

a.

the higher boiling point: diethyl ether or butyl alcohol?

b.

the greater solubility in water: 1-butanol or 1-pentanol?

c.

the higher boiling point: hexane or isohexane?

d.

the higher boiling point: pentylamine or ethylmethylamine?

e.

the greater solubility in water: ethyl alcohol or ethyl chloride?

9.

What are the common and systematic names of the following compounds?

a.

CH

3

CHCH

2

CH

2

Br

CH

3

b.

CH

3

CHCH

2

CH

2

OH

CH

3

c.

CH

3

CHCH

2

CH

2

NH

2

CH

3

10.

Draw the more stable conformer of:

a.

cis

-1-

sec

-butyl-4-isopropylcyclohexane

b.

trans

-1-

sec

-butyl-4-isopropylcyclohexane

c.

trans

-1-

sec

-butyl-3-isopropylcyclohexane

11.

Draw the structure for each of the following:

a.

a secondary alkyl bromide that has three carbons

b.

a secondary amine that has three carbons

c.

an alkane with no secondary hydrogens

d.

a constitutional isomer of butane

e.

three compounds with molecular formula C

3

H

8

O

12.

Name the following compounds:

a.

CH

3

CHCH

2

CH

2

CHCH

3

CH

3

CH

2

CH

3

d.

Cl

CH

3

Br

b.

CH

3

CHCH

2

CH

2

CH

2

CH

2

CH

2

Br

OH

e.

CH

3

CH

2

CH

2

CHCH

2

OCH

2

CH

2

CH

2

CH

3

CH

3

c.

CH

3

CHCH

2

CHCH

2

CH

2

CH

3

Cl

OH

f.

CH

3

CH

2

CH

2

NHCH

2

CH

2

CHCH

2

CH

3

CH

3