I'm supposed to find the product of rearrangement the chemical compound shown below undergoes when exposed to a nucleophile OEt-
. I thought that favorskii rearrangment could occur since there is an alpha hydrogen. If this is correct, then is the mechanism below right ? What makes no sense to me is the intermediate formed in the 3rd step. The 2nd image shows a different intermediate formed, which should be more stable. The carboanion formed is tablized by Br an electron withdrawing group. In the 1st case, the carboanion is less stable since it is attached to alkyl electron donating groups. The soln manual shows , however, that the product formed is the 1st one. Why is this so ? Perhaps the whole mechanism is incorrect ?
P.S. I skipped the details when writing the mechanism to save time but I think there should be no confusion.
1st mechanism :
2nd mechanism :