Organic Chemistry

(Dana P.) #1
Problems 233

g. h.


  1. Mevacor®is used clinically to lower serum cholesterol levels. How many asymmetric carbons does Mevacor®have?

  2. Indicate whether each of the following pairs of compounds are identical or are enantiomers, diastereomers, or constitutional
    isomers:
    a. i.


b. j.

c. k.

d. l.

e. m.

f. n.

g. o.

h. p.
Cl
Cl and

Cl

C Cl

H

CH 3 CH 2 CH 3 and

CH 2 Cl

C

H

CH 3 CH 2 Cl

CH 2 CH 3

C

C

Cl H and

CH 3 H

CH 3

CH 2 CH 3

C

C

H CH 3

H Cl

CH 2 CH 3

CH 3

CH 2 OH

and H

CH 2 CH 3
CH 3 CH 3
CH 2 CH 3

CH 2 OH
H

CH 3
CH 3
and

H 3 C

CH 3
CH 3

H 3 C

and

CH 2 CH 3

CH 3

Br

and

H 3 C

H 3 C

H H CH 3

CH 3

CC
Br

and CCCC
H 3 C

H

H

H 3 C CH 3

Br

CH 3

Br

CC CC

CH 3

HO H and
HCl

CH 3

CH 3

HOH
Cl H

CH 3

CH 2 CH 3

HO H and
HCl

CH 3

CH 3

HO H
HCl

CH 2 CH 3

CH 3

H CH 3

and
CH 3

H 3 C

H

Br H H

H

H

Br

and

H

Br

H

Br

and

H

Br H H

Br Br H

Br

and HCl

Cl H

Cl H

HCl

and HCl

Cl H

HH

Cl Cl

H Cl and

HCl

HH

Cl Cl

Mevacor

CH 3

HO O

O
O

O
CH 3

H 3 C

CH 2 CH 3

HO H
HCl

CH 3

CH 2 CH 2 CH 2 OH

HO CH 3

CH 2 OH
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