CH 202
Exam #1
February 12, 2001

Name ______________________________

Page

Points

1

______(12)

2

______(10)

3

______(19)

4

______(16)

5

______(14)

6

______(12)

7

______(14)

8

______(03)

Total

______(100)

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

Br

OCH3

F

COOH

NH2

Br

H3C

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

m-methylphenol

2,2-Diphenyl-3,3-dibromopentane

o-dichlorobenzene

1

2. Draw a resonance structure for each molecule below and circle the most important
contributor. (6 pts)

CH2

CH3

H3C

N

CH3

HC

HC

C

H2C

CH2

N

3. What two compounds would you employ to synthesize the following compound? (4 pts)

CO2CH3

CO2CH3

H

H

2

4. Predict the product from a Diels-Alder Reaction between the following compounds:
Show stereochemistry where appropriate. (15 pts)

C

C

CO2CH3

CO2CH3

O

O

O

O

OCH3

O

H3CO

5. Draw 2 resonance structures for each of the following carbocations: (4 pts)

CH2

3