The work-up procedure calls for washing the crude 2-chloro-2-methylbutane with cold 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 the sodium bicarbonate. Discuss the relative advantages and disadvantages of using these two basic solutions in the work-up.

c. On the basis of your answer to b, why were you instructed to use sodium bicarbonate, even though it is more difficult to handle?

d. What is the purpose of the final wash of the organic layer with saturate sodium chloride solution in the purification process?