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

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

a. Propose a mechanism for the reaction.

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.

(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.

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.