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?

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.

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

c.

d.

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.

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?