User:Mattyerou/sandbox

Reaction Mechanism
The α-haloester undergoes single electron transfer with zinc dust 1 and rearranges to eliminate the halide 3. Another single electron transfer occurs and the resulting ion 4 coordinates to zinc metal. The oxygen on an aldehyde or ketone also coordinates to the zinc to form the six-member chair like transition state 5. A rearrangement occurs in which zinc switches to the aldehyde or ketone oxygen and a carbon-carbon bond is formed 6. Acid workup removes zinc 7,8 to yield ZnX2 (zinc(II)) and a β-hydroxy-ester 9.