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Chapter 5 199

Copyright © 2017 Pearson Education, Inc.

44.

a.

CH

2

CHCH

2

CH

2

CH

2

CH

3

1-hexene

CH

3

CH CHCH

2

CH

2

CH

3

2-hexene

CH

3

CH

2

CH CHCH

2

CH

3

3-hexene

CH

2

CCH

2

CH

2

CH

3

2-methyl-1-pentene

CH

2

CHCHCH

2

CH

3

3-methyl-1-pentene

CH

2

CHCH

2

CHCH

3

4-methyl-1-pentene

CH

3

CH

3

CH

3

C CHCH

2

CH

3

2-methyl-2-pentene

CH

3

CH CCH

2

CH

3

3-methyl-2-pentene

CH

3

CH CHCHCH

3

4-methyl-2-pentene

CH

3

CH

3

CH

3

CH

2

CCHCH

3

2,3-dimethyl-1-butene

CH

3

CCH CH

2

3,3-dimethyl-1-butene

CH

3

CH

2

C CH

2

2-ethyl-1-butene

CH

3

CH

3

CH

2

CH

3

CH

3

C CCH

3

2,3-dimethyl-2-butene

CH

3

CH

3

CH

3

CH

3

CH

3

b.

Of the compounds shown in part

a

, the following can have

E

and

Z

isomers:

  2-hexene, 3-hexene, 3-methyl-2-pentene, 4-methyl-2-pentene

c.

CH

3

C CCH

3

CH

3

CH

3

This compound is the most stable.

It has four alkyl substituents

bonded to the

sp

2

carbons.

d.

CH

2

CHCH

2

CH

2

CH

2

CH

3

CH

2

CHCH

2

CHCH

3

CH

3

CH

2

CHCHCH

2

CH

3

CH

3

CCH CH

2

CH

3

CH

3

CH

3

These compounds are the least stable.

Each has only one alkyl substituent bonded to the

sp

2

carbons.

45.

a.

1

E

2

-3-methyl-3-hexene

b.

trans

-8-methyl-4-nonene or

1

E

2

-8-methyl-4-nonene

c.

trans

-9-bromo-2-nonene or

1

E

2

-9-bromo-2-nonene

d.

2,4-dimethyl-1-pentene

e.

2-ethyl-1-pentene

f.

cis

-2-pentene or

1

Z

2

-2-pentene