CHM 422 Organic Synthesis, Dr. Laurie S.

Starkey, Spring 2014

Final Exam
Name:__________________________________

p1

40

p4

40

I. (20 pts) Provide the missing reagents/structures

(AG) for each step of the following synthesis.
Some transformations may require two steps.

p2

40

p5

40

p3

40

Total

200

OH

OH

1) A

2) B

OH

OH
OMOM

OMOM
O
Ph3P

OTBS

OTBS

1) E

2) F

O
OMOM

OH

OMOM

II. (20 pts) Predict the major product(s) expected for each of the following reactions. Remember
to indicate stereochemistry, when appropriate. If no reaction is expected, write N/R.
Br
CH2(CO2Et)2

H3O+

EtONa
EtOH

1) Ph2CuLi
2) H3O+

KOH, H2O,

O
CN

(Robinson)
H
N
O

OCH3

1) LiAlH4
2) H3O+

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III. (80 pts) Provide the reagents necessary to transform the given starting material into the
desired product. More than one step may be necessary. It may help to do a retrosynthesis first.
a.
OH

O
CH3CH2CH2 C H

CH3CH2CH2

C CH3
CH2CH3

b.

H C C

CH3

O
EtO

c.

CH3

CH3

H
N

O
Ph

d.

e.

Ph
Ph

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III. (cont'd) Provide the reagents necessary to transform the given starting material into the desired
product. More than one step may be necessary. It may help to do a retrosynthesis first.
f.

OH

NH2

CO2Et

g.
EtO2C

CO2Et
CO2Et

(racemic)

OH
h.

HO
O

i.

OH

j.

O
Ph

O
H

Ph

OH
CH3

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IV. (40 pts) Synthesize the following target molecules. Each synthesis must form at least one
new CC bond. You may use any commercially available starting materials, reagents.
a.
O

b.

c.

Br

(using the disconnection

shown and using alcohol
starting materials as the only
source of carbon)

d.

O
O

from acyclic starting materials

(containing no rings)

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V. (40 pts) Synthesize the following target molecules. Each synthesis must form at least one
new CC bond. You may use any commercially available starting materials, reagents.
e
Br

HO

CO2H

f.
(using alkyl halide
starting materials as the
only source of carbon)

O
g.

CH3

(using the disconnection

shown as the new C-C bond)

h.

(using the disconnection

shown as the new C-C bond)

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