CH 202
Exam #3
March 17, 2000

Name ______________________________

Page

Points

1

______(12)

2

______(26)

3

______(21)

4

______(14)

5

______(14)

6

______(13)

Total

______(100)

1 (a)Provide IUPAC names for the following molecules. Don't forget to indicate stereochemistry when
applicable. (6 pts)

O

H

Br

O

H

Br

H3C

CH

CH3

CH3

O

(b) (6 pts) Provide structures for the following molecules.

Ethyl methyl ketone

4-Penten-2-one

3,5 Dimethyl benzaldehyde

1

3. Show the structure of the major product for each reaction. (8 pts)

HNO3

H2SO4

SO3

H2SO4

OCH3

O

NO2

NH

O

H3C

H3C

O

4. Show the structure of the majormono-substitution product resulting from electrophilic aromatic
substitution on one of the rings for each of the following reactions. (8 pts)

CH2CH2

O

NO2

O

H3C

Br2

FeBr3

Br2

FeBr3

5. Starting with tolueneshow the steps necessary to synthesize the following compound. (10 pts)

COOH

NO2

2

6. Draw the structures of the products of the following reactions. (21 pts)

H3C

C

CH3

O

O

Cl

C

N

O

O

+H2O

1. LiAlH(OtBu)3

2. H2O

1. DIBAL-H

2. H2O

1. DIBAL-H

2. H2O

H

O

HO

NH2

CH3

O

1. HCN, CN-

2. HCl/H2O, reflux
(hydrolysis)

CH3

O

H2C

P(Ph)3

3