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When we are reacting 2 moles of an aldehyde /ketone ( with alpha H ) with OH- as base to form aldol first step is formation of Enolate ion by reaction of OH- with acidic alpha H, second step is reaction of Enolate ion with second molecules of aldehyde ( we know we took OH- as base because it doesn't react with all molecules of aldehyde converting them into Enolate , so an Enolate ion will be surrounded by aldehydes) . So here comes my doubt Enolate ion react from carbon end on the carbonyl group .We know carbonyl group is a hard electrophile And enolate ion has a property that it reacts with oxygen end with a hard nucleophile because polarity is a more important factor and carbon end with soft nucleophiles this property is beautifully illustrated in alpha alkylation of carbonyl groups. So why in aldol reaction even though carbonyl group is attacked the Carbon end attack is more prominent .

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    $\begingroup$ Consider the molecule created if it does. Is this a stable species? Or is it soemthing that will break down quickly to recreate the enolate? Is it possibile that this happens all the time and is in equilibrium with enolate + aldehyde but it just does not lead to any product ? $\endgroup$
    – Waylander
    Sep 27 at 21:27

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