Q.10P - Organic Chemistry (Mcmurry)

Question

What product would you expect from Claisen rearrangement of 2-butenyl phenyl ether?

Step-by-Step Solution

Answer

Answer

The product expected from Claisen rearrangement of 2-butenyl phenyl ether is,

Step-by-Step Solution Step 1: Claisen rearrangement

In Claisen rearrangement, new C-C bonds are formed by Claisen [3,3], and after re-aromatization, phenol product is formed.

Step 2: Formation of TS and intermediate

A transition state with new C-C bonds formation and intermediate with enone formation forms.

Step 3: The product expected from Claisen rearrangement of 2-Butenyl phenyl ether

In rearrangement, the ether with the groups is drawn and positioned so that they will appear in the product. The six bonds can either be broken or formed in the product and are shown by dash lines in the transition state. The bonds are redrawn at the intermediate enone, which is again rearranged to form a more stable phenol.

                   Claisen rearrangement of 2-Butenyl phenyl ether