What additional starting material is required for the following reaction?

+ ?

A
B
C
D
E

A
B
C
D
E
A Correct, this molecule can only react as the substrate to the nucleophilic attack as it can not form an enolate. No, this molecule will not work well as it can form an enolate and you will get a mixture of products. No, you need a carbonyl group in the molecule so the enolate can do a nucleophilic attack on it. No, the acid is more reactive to nucleophilic attacks and two molecules of the enolate will add to produce a 3o alcohol. No, the ester is more reactive to nucleophilic attacks and two molecules of the enolate will add to produce a 3o alcohol. Review Carey 5th Ed. Chapter 18 section 10