1. Predict the major products of the following reactions.

Show proper stereochemistry whenever

possible or applicable.
a.

HO-
b.

CH3O-
c.

-
CN
d.

e. tBuO-

2. Provide a reasonable mechanism that would result in the formation of the products shown below.
CH3CH2OH
+

3. Is A or B the major product that is produced by the reaction shown below? Pick one and explain
why you think that is the answer.

CH3O-

A B
4. Propose how you would synthesize the following compounds from the given starting materials, or
provide the necessary reactants/reagents needed to synthesize a given compound. There is no need
to show the mechanism of how the final product is obtained.

a.

b.

c.

d.

s
 Answers
1a.

1b.

1c.

1d.

1e.

2.

3. A is the major product. An E2 reaction will occur with the reactants and reagents that are provided. E2
reactions have the constraint that the hydrogen and the halide that are being eliminated must be anti-
periplanar. Since the position of the ethyl group tells us that the hydrogen bonded to that carbon is not
anti-periplanar to the chlorine, A must be the major product.
 tBuO- Br2 1. 3x NaNH2
4a.
Δ CH2Cl2 2. CH3Br

Na NH3(l), -78°C

1. O3, -78°C
2. (CH3)2S

4b.

1. 2x NaNH2 Na H2
4c.
2. CH3CH2Br NH3(l), -78°C Pd/C

HBr tBuO- Br2 2x NaNH2

4d.
Δ CH2Cl2
H2SO4, H2O, HgSO4