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Naked anions in polar protic solvents are more reactive as
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- more reactive than a ketone (the enolate anion formed on deprotonation (conjugate base) is stabilized by the electron-withdrawing halogen
- enolate is ambidentate, it can undergo C-attack or O-attack using the O or the alpha carbon as the nucleophilic center
- strong nucleophile attacks, then oxygen gets protonated, or oxygen gets protonated and then weak nucleophile attacks