The compound pictured here is a thiol. (a) Draw its line structure, and (b) draw the structure of the disulfide formed when it is treated with an oxidizing agent (yellow = S). <IMAGE>

Complete the following equations (Hint: Answers may include concepts learned from previous organic chapters):

a. <IMAGE>

Which thiol will produce the following disulfide upon oxidation?

Draw product of the following reaction.

What disulfides would you obtain from oxidation of the following thiols?

a. CH₃CH₂CH₂SH

b. 3-Methyl-1-butanethiol (skunk scent)

Oxidation of a dithiol such as 2,5-hexanedithiol forms a six-membered ring containing a disulfide group as part of the ring. Draw the structure of this cyclic disulfide (Hint: Draw the starting compound in line structure format first). <IMAGE>

Complete the following equations (Hint: Answers may include concepts learned from previous organic chapters):

a. <IMAGE>