Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Predict the major product of the following aldol condensation reaction:
Correct answer
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Step-by-step solution
The given reactant is 4-methylpentanal, which has the structure CH ₃- CH ( CH ₃)- CH ₂- CH ₂- CHO . In the presence of a base ( OH ^- ), an aldol condensation takes place. The base removes an acidic -proton from one molecule of 4-methylpentanal to form an enolate ion: CH ₃- CH ( CH ₃)- CH ₂- CH ₂- CHO OH ^- CH ₃- CH ( CH ₃)- CH ₂- CH ⁻- CHO + H ₂ O This enolate acts as a nucleophile and attacks the electrophilic carbonyl carbon of a second molecule of 4-methylpentanal: CH ₃- CH ( CH ₃)- CH ₂- CH ₂- CHO + CH ₃- CH (