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606 Chapter 18

Copyright © 2017 Pearson Education, Inc.

24.

CCH

2

CH

3

O

CH

3

CH

2

CCl

AlCl

3

O

2. H

2

O

1.

CH

2

CH

2

CH

3

FeBr

3

Br

2

CH

2

CH

2

CH

3

Br

or

H

2

, Pd/C

H

2

NNH

2

HO

,

CCH

2

CH

3

O

CCH

2

CH

3

O

Br

CH

2

CH

2

CH

3

Br

CH

3

CH

2

CCl

AlCl

3

O

2. H

2

O

1.

Br

2

FeBr

3

or

H

2

, Pd/C

H

2

NNH

2

HO

,

h.

a.

b.

CH

3

COOH

COOH

CH

3

Cl

AlCl

3

HNO

3

H

2

SO

4

NO

2

O

4

c.

CH

3

CH

3

COOH

CH

3

Cl

AlCl

3

HNO

3

H

2

SO

4

NO

2

NO

2

O

4

d.

Cl

Cl

NO

2

Cl

NH

2

Cl

2

H

2

SO

4

HNO

3

FeCl

3

H

2

, Pd/C

e.

H

2

, Pd/C

NO

2

NO

2

NH

2

HNO

3

H

2

SO

4

Cl

2

FeCl

3

Cl

Cl

b.

2. H

2

O

2. H

2

O

HNO

3

H

2

SO

4

H

2

SO

4

1. CH

3

3

CCl/AlCl

O

1. CH

3

3

CH

2

CCl/AlCl

O

CH

2

CH

3

C

O

CH

3

C

O

CH

2

CH

3

C

O

SO

3

H

CH

3

C

O

NO

2

c.

CH

3

Cl

AlCl

3

CH

3

HNO

3

COOH

H

2

SO

4

COOH

NO

2

O

4