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Chapter 20 683

Copyright © 2017 Pearson Education, Inc.

19.

The hemiacetals in

a

and

b

have one asymmetric center; therefore, each has two stereoisomers. The hemi-

acetals in

c

and

b

have two asymmetric centers; therefore, each has four stereoisomers.

a.

Solved in the text.

b.    

O

OH

O

OH

H

3

C

H

3

C

O

OH

O

OH

H

3

C

H

3

C

c. 

O OH

H

O H

OH

d.     

CH

3

CH

2

CH

2

CH

3

CH

2

CH

2

CH

3

CH

2

CH

2

CH

3

CH

2

CH

2

O

OH

O

OH

O

OH

O

OH

20.

a.

O OH

CH

2

OH

HO

OH

OH

b.

O CH

2

OH

OH

HO

HO OH

c.

O

OH

CH

2

OH

HO

OH

OH

O

HO

CH

2

OH

OH

OH

HO

D

-glucose

L

-glucose

the mirror image of -

D

-glucose

-

-

21.

O

OH

OH

OH

HO

CH

2

OH

H