Aldol

In organic chemistry, an aldol describes a structural motif consisting of a 3-hydroxy ketone or 3-hydroxyaldehyde. Aldols are usually the product of aldol addition. When used alone, the term "aldol" may refer to 3-hydroxybutanal.[1]

Generalized structure of the aldol moiety: When R3 is -H, it is a β-hydroxy aldehyde, otherwise it is a β-hydroxy ketone.

Stereochemistry
Isomers of generalized aldol.

Despite having only two functional groups, many aldols can have complicated structures arising from the relative positions of the OH group and the substituent between it and the carbonyl.[2] Controlling reactions in order to favor the formation of one of these isomers is of great interest in the area of asymmetric synthesis.

Reactions

The chemistry of aldols is dominated by one reaction, dehydration:

RC(O)CH2CH(OH)R' → RC(O)CH=CHR' + H2O

Hydroxypivaldehyde is a rare example of a relatively robust aldol.

References
  1. "Cid 21282929".
  2. Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, ISBN 978-0-471-72091-1
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