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Why is it important to add acetone slowly and dropwise to the mixture? Aldol Con

ID: 589188 • Letter: W

Question

Why is it important to add acetone slowly and dropwise to the mixture?

Aldol Condensation: Synthesis of Dibenzylideneacetone

Step 1: Generation of an enolate in the presence of a base (catalyst) OH (Acetone) An enolate ion Step 2: Nucleophilic addition of an enolate to the electrophilic carbonyl carbon followed by protonation- An ALDOL (-Hydroxycarbonyl compound) > O C O OH +HO (Nucleophilic attack) (Protonation) An Aldol Catalyst Step 3: Dehydration on an aldo-> ,-unsaturated carbonyl compound OH + H20 HO An Aldol Benzalacetone Catalyst Benza!acetone has acidic -hydrogens; if excess benzaldehyde is used, the enolate generated from benzalacetone will react with another molecule of benzaldehyde (repeat the steps). Complete the following Step 4: An enolate generation from benzalacetone in the presence of a base OH an enolate ion Benzalacetone Step 5: Nucleophilic attack on another molecule of benzaldehyde followed by protonation Step 6: Dehydrationdibenzalacetone

Explanation / Answer

It is important to add acetone slowly and dropwise to the mixture in Aldol Condensation as the attack of an - carbon (in the form of an enolate ion) of acetone on an electropositive carbonyl of a benzaldehyde.i.e. also in the Synthesis of Dibenzylideneacetone deprotonation of acetone takes place in first step and generation of enolate ion which act as a nucleophile and attacks the electrophile.

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