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Chemistry LibreTexts

Crossed Aldol Reaction

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Crossed aldol reaction is a variation of aldol reaction.

aldol reaction:

crossedaldolreaction1.png

crossed aldol reaction:

crossedaldolreaction2.png

eg:

crossedaldolreaction3.png

Mechanism:
Step 1: The hydroxide ion deprotanates the enolizable aldehyde reversibly.

crossedaldolreaction4.png

Step 2: Enolate ion 1 preferentially adds to the non-enolizable aldehyde, which has the sterically less hindered and, therefore, more accessible carbonyl carbon.

crossedaldolreaction5.png

Step 3: Alkoxide ion 2 is protonated by water.

crossedaldolreaction6.png

see also crossed aldol condensation


This page titled Crossed Aldol Reaction is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Gamini Gunawardena via source content that was edited to the style and standards of the LibreTexts platform.

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