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Mechanism for Aldol Condensation o E H HO OH 11 II C H3O H CJ C. CH H2O C. CH c- H3C CH2 H3O C H3C C H2 H2 enolate Step 1 Step 2 Step 3 H H alkoxide hydroxy- ketone Summary: Step 1: Deprotonation (makes nucleophilic enolate) OH Step 2: Attack by nucleophile on electrophile Step 3: Protonate to give neutral hydroxy-ketone Step 4 Step 4: Deprotonate again (makes enolate) Step 5: Eliminate hydroxide to generate alkene pi bond Repeat o H II H Steps 1-5 O CO HO C CO H C Again C. C Step 5 II C C H3C C C. CH H H H H3C C H Dibenzalacetone Benzalacetone "enone" hydroxyenolate

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