What thiol is produced using thiourea and 1-chloropentane? 

The foul smell excreted by skunks is due to a number of thiols. Show how you would synthesize the following thiol using vinylcyclohexane?

Show how to synthesize isopropyl propyl sulfide using propan-1-ol and propan-2-ol.

When hunting dogs stand nose-to-nose with a skunk while barking furiously, they are often not aware of the skunk spray directed toward them. One method to reduce the amount of the odor is to use a bath that contains some mild dish detergents, dilute hydrogen peroxide, and sodium bicarbonate to wash the dog. If skunk oil contains two thiol derivatives shown below, explain how using this mixture can help to remove the skunk spray.

Similar to 2-mercaptopropan-1-ol, 2,5-dimercaptohexane-3,4-diol reacts with disulfide bridges. However, the equilibrium lies predominantly to the right in this reaction. Explain.

Starting with pure (S)-hexan-3-ol and any necessary reagents, show how the following can be synthesized:

(i) pure (S) enantiomer of 3-hexyl methyl sulfide

(ii) pure (R) enantiomer of 3-hexyl methyl sulfide