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21. Enolate Chemistry:Reactions at the Alpha-Carbon - Part 2 of 2
21. Enolate Chemistry:Reactions at the Alpha-Carbon - Part 2 of 2
24. Enolate Chemistry: Reactions at the Alpha-Carbon / Enolate Alkylation and Acylation / Problem 3

When an α-haloketone reacts with a hydroxide ion, a carboxylic acid is formed. This is known as a Favorskii reaction. Propose a suitable mechanism for the Favorskii reaction shown below. (Hint: The first step is deprotonation of the α-carbon that is not bonded to Br; the second step is the formation of a three-membered ring; and in the third step, HO acts as a nucleophile.)


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