13. Alcohols and Carbonyl Compounds

Give the structures of the intermediates represented by letters O, P, and Q in this synthesis.

Show how each of the following compounds could be prepared from the given starting material. Each requires a protecting group.

b.

A chemist failed to generate the diol using the reaction shown here.

(a) Suggest a reason why this reaction did not work as written.

(b) How could the reaction conditions be modified to allow formation of the diol? [It may require more than one step.]

Show how you would convert 3-bromocyclohexanol to the following diol. You may use any additional reagents you need.