(a) Show how you would synthesize the pure (R) enantiomer of 2-butyl methyl sulfide, starting with pure (R)-butan-2-ol and any reagents you need
(b) Show how you would synthesize the pure (S) enantiomer of the product, still starting with (R)-butan-2-ol and any reagents you need.

Thiols can be prepared from the reaction of thiourea with an alkyl halide, followed by hydroxide-ion-promoted hydrolysis.

b. What thiol will be formed if the alkyl halide employed is pentyl bromide?

Dithiothreitol reacts with disulfide bridges in the same way that 2-mercaptoethanol does. With dithiothreitol, however, the equilibrium lies much more to the right. Explain.

Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?

a.

Using an alkyl halide and a thiol as starting materials, how would you prepare the following thioethers?

b.

Show how you would synthesize the following:

e. cis-pent-2-en-1-thiol from a suitable alkenyl halide

Predict the product for each of the following reactions.

(c)

Authentic skunk spray has become valuable for use in scent-masking products. Show how you would synthesize the major component of skunk spray (3-methylbutane-1-thiol and but-2-ene-1-thiol) from any of the readily available butene or from buta-1,3-diene.

Many hunting dogs enjoy standing nose-to-nose with a skunk while barking furiously, oblivious to the skunk spray directed toward them. One moderately effective way of lessening the amount of odor is to wash the dog in a bath containing dilute hydrogen peroxide, sodium bicarbonate, and some mild dish detergent. Use chemical reactions to describe how this mixture helps to remove the skunk spray from the dog. The two major components of skunk oil are 3-methylbutane-1-thiol and but-2-ene-1-thiol.