1. When ethanethiol and n-butyl bromide are added to aqueous KOH, n-butyl ethyl sulfide is

formed. Explain.

2. When (R)-bromopropionic acid is exposed to aqueous KOH, (R)-lactic acid is formed.

Explain.

3. Two of the four optically active stereoisomers of 4-chloro-3-hexanol form an optically

inactive compound A, C₆H₁₂O, when treated with aqueous KOH. Which ones are they?

What is the structure of A? [Draw their structures, use R,S designations, and provide a

mechanism and explanation for the process.

4. The stoichiometric reaction of ammonia with n-butyl iodide can be used to prepare n-

butylamine. Show a mechanism for this reaction and explain how the free amine, not its

salt, can be isolated.

5. Unfortunately, the reaction described in #4 has a complication. Di-n-butylamine is also

formed. Explain its formation.

6. What change(s) in the reaction conditions of #4 can be made to repress the formation of di-

n-butylamine?

7. (2R,4R)-4-bromo-4-methyl-2-hexanol gives two optically active diols when exposed to water.

However, (R)-3-bromo-3-methylhexane gives racemic alcohol under the same conditions.

Explain.

8. Show how (2R,5R)-2,5-dimethyltetrahydrofuran 2 can be formed from (2R,5S)-5-

bromo-2-hexanol 3. [Cf. #3]. What stereoisomer of 3 leads to the enantiomer of 2 [ent-

2]? [Structure 1 is 2,5-dimethylfuran].

9. Methyl t-butyl ether (MTBE) is a gasoline additive. How can it be prepared from 2-chloro-

2-methylpropane?

10. MTBE is made industrially from 2-methylpropene (isobutylene) using an acid catalyst instead

of an alkyl halide (see #9). Write a mechanism for this reaction. What is the common intermediate in #9

and #10?