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414 Chapter 12

Copyright © 2017 Pearson Education, Inc.

12.

To start peroxide formation, the chain-initiating radical removes a hydrogen atom from an

a

-carbon of the

ether.

a. D

is most apt to form a peroxide, because removal of a hydrogen from an

a

-carbon forms a secondary

radical.

b. B

is least apt to form a peroxide, because it does not have any hydrogens bonded to its

a

-carbons.

13.

CH

3

Br

+

CH

3

Br

CH

3

HBr

+

CH

3

Br

Br

Br

+

14.

a.

CH

3

C CHCH

3

CH

3

+

HBr

CH

3

C CH

2

CH

3

CH

3

Br

CH

3

C CHCH

3

CH

3

+

HCl

CH

3

C CH

2

CH

3

CH

3

Cl

b.

CH

3

C CHCH

3

CH

3

+

HBr

CH

3

C CH

2

CH

3

CH

3

Br

CH

3

C CHCH

3

CH

3

+

HCl

CH

3

C CH

2

CH

3

CH

3

Cl

c.

d.

15.

a.

CH

3

CHCH

3

+

Cl

2

hv

CH

3

CH

3

CHCH

2

Cl

achiral

CH

3

CH

3

CCH

3

achiral

CH

3

Cl

b.

CH

3

CH

2

CH

2

CH

3

CH

3

CH

2

CH

2

CH

2

Cl

achiral

+

Cl

2

hv

C

CH

2

CH

3

CH

3

Cl

H

C

CH

2

CH

3

CH

3

Cl

H

+

chiral

chiral

enantiomers