Crossed Aldol Reaction

Crossed aldol reaction is a variation of aldol reaction.

aldol reaction:



crossed aldol reaction:



eg:



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



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



Step 3:  Alkoxide ion 2 is protonated by water.



see also crossed aldol condensation

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