mechanism

Chem 351 Test 4 Fall 2002 Dr. Knight Name
_____________________

1. (5 points each) Please indicate the major organic products from the
following reactions. Designate the reaction category (SN1, SN2, E1,
E2) where applicable.

2. (10 points) (from problem 9.33) What nucleophiles could be used to
react with butyl bromide to prepare the following compounds

a. CH3CH2CH2CH2OCH3

b. CH3CH2CH2CH2SH

3. (30 points, 10 each) For each of the following reactions, show the
major product(s) of the reaction, and present a stepwise mechanism using
the curved arrow notation. Designate the reaction category (SN1,
SN2, E1, E2) where applicable.

a.

b.

c.

4.(10 points) Fill in the blank.

5. (10 points) Fill in the blank.

6. (10 points) (From 9.20) Which alkyl halide would you expect to be
more reactive in an Sn2 reaction? Circle the more reactive one.

CH3CH2CH2Br or CH3CH2CH2I

7. (10 points) For the following reaction, the rate increased with
increasing concentration of 2-bromopropane, but was not changed by
increasing the concentration of pentanol. What is the likely mechanism.


Extra Credit. (5 points) Suggest a synthesis of the product on the right
from the material on the left.