21.5 Aldol Reactions

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    Self-Aldol Reactions

    self-aldol reaction

    Base-Catalyzed Aldol Mechanism

    -enolate adds to a ketone or aldehyde

    base-catalyzed aldol mechanism

    Acid-Catalyzed Aldol Mechanism

    -enol adds to a ketone or aldehyde

    acid-catalyzed aldol mechanism

    Crossed (Mixed) Aldol Reactions

    The following strategies are preferred for forming a single major product:

    1. Using LDA to form the enolate.

    crossed aldol reaction using LDA

    2. The nucleophile has the only enolizable hydrogens and the other molecule is the better electrophile.

    crossed aldol reaction 02

    Intramolecular Aldol Reactions

    -Generally only 5- or 6-membered rings will form

    intramolecular aldol reaction