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.

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

b.

(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)

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.

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.