Synthesis of alcohols using Grignard reagents I

23-64 The Stork enamine reaction and the intramolecular aldol reaction canbe carried out in sequence to allow the synthesis of cyclohexenones.For example, reaction of the pyrrolidine enamine of cyclohexanonewith 3-buten-2-one, followed by enamine hydrolysis and base treat-ment, yields the product indicated. Write each step, and show themechanism of each.

SOLVED:Propose a synthesis of beginning with cyclohexanone, and 3 -bromopropanol. [Hint: Beware of a possible pitfall in planning this synthesis (recall Section 8-9).]

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