13. Alcohols and Carbonyl Compounds

Predict the product of the diorganocuprate cross-coupling reactions shown.

(c)

Suggest a synthesis of the following molecule starting with the reagents shown, using cuprate cross-coupling as the key step.

Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with the molecule at the left.

(d)

Suggest a synthetic scheme, involving a protecting group, to generate the molecule shown starting with the molecule at the left.

(b)

Predict the product of the following reactions.

(b)

Suggest a series of steps involving a cuprate reagent that would convert the reactant on the left to the product on the right. The ideal number of steps is shown.

(c)

Suggest a reagent and a reactant that could be used to form the following molecules by conjugate addition of a cuprate. There can be multiple possibilities.

(c)

To this point, we have seen four reactions that can be done by Gilman reagents. What are they? What do they have in common?

Phenol oxidation can be coupled with other reactions to form new C―C bonds using reactions studied previously. Predict the product of the following series of reactions.

(b)