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.

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

c.

d.

Thiols are prone to dimerize through the formation of a disulfide bond in a reaction that stylists use to induce permanent curls in hair. What type of reagent would you use to effect this transformation?

Starting with hydrogen sulfide, suggest a synthesis of the following thioether that makes use of two different haloalkanes.

Show how you would synthesize butyl isopropyl sulfide using butan-1-ol, propan-2-ol, and any solvents and 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.