Q33E - Organic Chemistry (Mcmurry)

Question

The final step in attempting to synthesize Laurene, a hydrocarbon isolated from the marine alga Laurencia glandulifera, involved the Wittig reaction shown. The product obtained, however, was not Laurene but an isomer. Propose a mechanism to account for these unexpected results.

Step-by-Step Solution

Answer

Step 1: Laurene

Laurene is different in stereochemical configuration from the starting compound. So, enolization and isomerization have occurred in the above process.

Step 2: Mechanism

The mechanism for the above process is,

                                      Mechanism of the reaction