14. Compounds with Oxygen or Sulfur

Draw product of the following reaction.

Which thiol will produce the following disulfide upon oxidation?

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).

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

a.

Propanol is very soluble in water, but ethanethiol and chloroethane are only slightly soluble. Explain.