Can cinnamaldehyde undergo self aldol condensation
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No aldol condensation is not possible here, as you would have to extricate an alpha hydrogen(alpha to the carbonyl group), but if you do extricate a hydrogen atom from the alpha position it would result in the formation of Vinylic Carbanion which is very very unstable.
Thus the molecule would not want the alpha hydrogen to get extricated, thus aldol reaction would not proceed as you need to remove the alpha hydrogen in order to proceed forward with the reaction.
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