CH 202
Exam #1
February 24, 1997

Name ______________________________

Page

Points

1

______(12)

2

______(22)

3

______(14)

4

______(17)

5

______(15)

6

______(12)

7

______(08)

Total

______(100)

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

OH

CH2CH3

COOH

CH2CH3

CH3

CH3

H3C

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

1-chloro-2-phenyl-3-bromopentane

2,4,6-trinitrotoluene (TNT)

meta-toluic acid

1

2. Label the following planar molecules as aromatic or nonaromatic. (8 pts)

N

CH3

N

N

N

N

3. Draw the structure of the product obtained from the following reaction. (3 pts)

CH2CH3

C

CH2CH3

CH3CH2

CH2CH3

hot KMnO4

4. Rank the following compounds with respect to their reactivity toward bromination with Br2/FeBr3.
Label #1 as the fastest and #4 as the slowest. (4 pts)

CH3

Cl

OCH3

C

O

CH3

______

______

______

______

5. Show a complete mechanism, using arrows to push electrons, for the following reaction. (You do not
have to show resonance structures for the intermediates). (6 pts)

2

6. Assign each signal in the 1H nmr spectrum with the appropriate letter. (14 pts)
a.

b.

H3C

CH2

O

CH2

OH

O

a

b

c

d

3