Starting with cyclohexanone,how could you prepare the diketone below?
A)Treat cyclohexanone with a base under thermodynamic conditions.
B)Hydrogenate cyclohexanone with Raney nickel.
C)Convert cyclohexanone into the a-bromoketone and then react this with the enolate of cyclohexanone.
D)Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone.

Question

Starting with cyclohexanone,how could you prepare the diketone below? 
A)Treat cyclohexanone with a base under thermodynamic conditions. 
B)Hydrogenate cyclohexanone with Raney nickel. 
C)Convert cyclohexanone into the a-bromoketone and then react this with the enolate of cyclohexanone. 
D)Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone.

Quizplus · Accepted Answer

The best choice for preparing the diketone involves converting cyclohexanone into the a-bromoketone and reacting this with the enolate of cyclohexanone, which will result in the formation of the desired diketone. This process takes advantage of the reactivity of the α-bromo-ketone towards enolates, as the bromine atom facilitates the formation of a carbanion at the α-carbon, which can then attack the enolate. The other options (A, B, and D) do not lead to the desired diketone.

Starting with Cyclohexanone,how Could You Prepare the Diketone Below