2-Chloro-2-Methylbutane Exercises:

1. The work-up procedures for the reactions in this section call for washing the "crude" chloroalkanes with sodium bicarbonate solution.

a. What purpose does this wash serve ?

b. This washing procedure is accompanied by vigorous gas evolution, which increases

the difficulty of handling and requires considerable caution. Alternatively, one

might consider using a dilute solution of sodium hydroxide instead of sodium

bicarbonate. Discuss the relative advantages and disadvantages of using these two

basic solutions in the work-up. On the basis of these considerations, why were

you instructed to use sodium bicarbonate, even though it is more difficult to

handle ?

2. Why is saturated sodium chloride solution, rather than dilute solution, specified for the final washing of the product ?

3. The procedures call for the drying of the chloroalkanes with anhydrous magnesium sulfate. Could solid sodium hydroxide or potassium hydroxide be used for this purpose? Explain.

4. Determine the limiting reagent for the preparation of 2-chloro-2-methylbutane, and calculate the theoretical yield of the product.

5. Why is this reaction carried out at room temperature rather than at elevated temperatures?

6. Is this reaction an S_N1 or S_N2 process ?

7. Write the structures of any possible side products that might be formed in this reaction.

8. After the initial reaction is carried out, and the crude product is isolated, it is washed

with dilute sodium bicarbonate solution. What is the purpose for this wash, and could

dilute sodium hydroxide be used instead of sodium bicarbonate ? Explain briefly.