CH 202
Exam #2
February 28, 2001

Name ______________________________

Page

Points

1

______(14)

2

______(10)

3

______(20)

4

______(14)

5

______(00)

6

______(16)

7

______(16)

8

______(10)

Total

______(100)

1. Which of the following labeled protons will come farther downfield.

AorB

(4 pts)

H

A

H
B

2. Label the following planar molecules as aromatic or nonaromatic. (10 pts)

O

N

H
N

CH3

H3C

N

H

H

1

3. Show a detailed arrow pushing mechanism for the following reaction. Show at least 2 more resonance
structures for the intermediate arenium ion. (10 pts)

HNO3/H2SO4

NO2

2

4. Fill in the reagents necassary to carry out the following electrophilic aromatic substitutions. (12 pts)

C

Br

O

SO3H

5. Briefly but completely explain which of the following molecules is the strongest acid. The bolded
protons are the acidic protons in each molecule. Wherever possible, DRAW STRUCTURES to complete
your answer. (4 pts)

H

H

H

H

6. Predict the major product for the following reaction. (4 pts)

H3C

CH

CH2

CH3

Cl

AlCl3

+

3