a. Optically active 2-bromobutane undergoes racemization on treatment with a KBr solution. Write a mechanism for this racemization below.

b. In contrast, optically active 2-butanol not racemize on treatment with a KOH solution.

Explain why a reaction like that seen in (a) above does not occur.

c. Optically active 2-butanol does racemize in dilute acid solution. Propose a mechanism for this racemization below.