Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Identify the major product formed in the following reaction: +
Correct answer
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Step-by-step solution
The reaction between benzaldehyde and acetone in the presence of a base and heat is a crossed aldol condensation (Claisen-Schmidt condensation). Acetone has -hydrogens, so it forms an enolate ion in the presence of OH^- . CH₃-CO-CH₃ + OH^- CH₃-CO-CH₂^- + H₂O Benzaldehyde lacks -hydrogens and acts as the electrophile. The enolate attacks the carbonyl carbon of benzaldehyde. C₆H₅-CHO + CH₃-CO-CH₂^- C₆H₅-CH(O^-)-CH₂-CO-CH₃ Protonation yields the -hydroxy ketone. C₆H₅-CH(O^-)-CH₂-CO-CH₃ + H₂O C₆H₅-CH(OH)-CH₂-CO-CH₃ + O