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Crossed Aldol Condensation

[ "article:topic", "authorname:ggunawardena" ]
  • Page ID
    39390
  • Crossed aldol condensation is a variation of aldol condensation.

    aldol condensation:

     

    crossed aldol condensation:

    eg:

    Mechanism

    Step 1:  The hydroxide ion deprotonates 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.

     

     

    Step 4: Aldol 3 is an enolizable aldehyde.  A small amount of it is converted to the corresponding enolate ion (4) by the hydroxide ion.

     

     

    Step 5: Enolate ion 4 loses a hydroxide ion.

     

     

    Step 1 through 3 are a crossed aldol reaction, steps 4 and 5 a 1,2-elimination via E1cB mechanism. Thus, crossed aldol condensation is crossed aldol reaction followed by 1,2-elimination.