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Chapter 21 729

Copyright © 2017 Pearson Education, Inc.

c.

(CH

3

)

2

CHCH O

O

NH

2

valine

NH

3

H

2

Pd/C

(CH

3

)

2

CHC

NH

excess

(CH

3

)

2

CHC O

Η

O

trace

acid

C

O

C

O

C

O

d.

CH COC

2

H

5

O

C

2

H

5

OC

Br

+

N

K

+

O

O

-bromomalonic ester

potassium phthalimide

N

O

O

C COC

2

H

5

COC

2

H

5

H O

O

N

O

O

C COC

2

H

5

COC

2

H

5

O

O

CH

3

CH

2

OH

CH

3

CHBr

CH

3

N

O

O

C COC

2

H

5

COC

2

H

5

O

O

Br

CH CH

3

CH

3

HCl, H

2

O

CH O

C

O

valine

CH(CH

3

)

2

H

3

N

+

+

CO

2

COOH

COOH

+

phthalic acid

O

CH

3

CH

2

O

+

2 CH

3

CH

2

OH

e.

HCl, H

2

O

CH O

valine

CH(CH

3

)

2

H

3

N

+

+

CO

2

+

CH COC

2

H

5

O

C

2

H

5

OC

N

O

CH

3

CH

2

O

H CCH

3

O

C COC

2

H

5

O

C

2

H

5

OC

O

CH

3

CHBr

CH

3

CH

2

O

CH

3

C COC

2

H

5

O

C

2

H

5

OC

O

Br

CH

H

3

C CH

3

3

3

CH

3

acetic acid

acetamidomalonic ester

N

H CCH

O

N

H CCH

O

O

C

O

C

O

+

2 CH

3

CH

2

OH