Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Identify the major product Y in the following reaction sequence:
Correct answer
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Step-by-step solution
The reaction of cyclopentanone with the secondary amine, N-ethyl-N-methylamine, in the presence of dilute acid forms an enamine (X). The enamine (X) undergoes alkylation when treated with methyl bromide ( CH₃Br ). The nucleophilic -carbon of the enamine attacks the methyl group, forming an iminium salt intermediate. Hydrolysis of this iminium salt with H₃O^+ yields the -alkylated ketone, which is 2-methylcyclopentanone (Y), and regenerates the secondary amine, N-ethyl-N-methylamine (Z). The regenerated secondary am