Question

Question: Draw a stepwise mechanism for the formation of A from an alcohol and acid chloride. A was converted in one step to Blattella quinone, the sex pheromone of the female German cockroach Blattella germanica.

Short answer

Answer

Reaction mechanism for formation of A:

Step-by-step solution

Step-by-Step Solution Step 1: Acid chlorides

• Acid chlorides, also known as acyl chlorides, contain a chlorine atom attached to the acyl group.

• They readily react with the nucleophile to give a nucleophilic substitution product and HCl as a byproduct.

Reaction mechanism for the formation of A

• The nucleophile (alcohol) attacks the carbonyl group of acyl chloride, forming an ${\mathrm{sp}}^3$hybridized carbon.

• Loss of a proton, followed by elimination of the leaving group ( ), forms the required product A.

Reaction mechanism