Disulfides are compounds that have \(S-S\) bonds, like peroxides have
\(\mathrm{O}-\mathrm{O}\) bonds. Thiols are organic compounds that have the
general formula \(\mathrm{R}-\mathrm{SH}\), where \(\mathrm{R}\) is a generic
hydrocarbon. The \(\mathrm{SH}^{-}\) ion is the sulfur counterpart of hydroxide,
\(\mathrm{OH}^{-}\). Two thiols can react to make a disulfide,
\(\mathrm{R}-\mathrm{S}-\mathrm{S}-\mathrm{R} .\) (a) What is the oxidation
state of sulfur in a thiol? (b) What is the oxidation state of sulfur in a
disulfide? (c) If you react two thiols to make a disulfide, are you oxidizing
or reducing the thiols? (d) If you wanted to convert a disulfide to two
thiols, should you add a reducing agent or oxidizing agent to the solution?
(e) Suggest what happens to the H's in the thiols when they form disulfides.