Aldol reaction

Aldol Addition
Reaction type Coupling reaction
Reaction
Ketone or Aldehyde
+
Ketone or Aldehyde
β-hydroxy Aldehyde
or
β-hydroxy Ketone
Conditions
Temperature
-Δ, ~-70°C[a]
Catalyst
OH or H+
Identifiers
Organic Chemistry Portal aldol-addition
RSC ontology ID RXNO:0000016

The aldol reaction (aldol addition) is a reaction in organic chemistry that combines two carbonyl compounds (e.g. aldehydes or ketones) to form a new β-hydroxy carbonyl compound. Its simplest form might involve the nucleophilic addition of an enolized ketone to another:

Prototype aldol reaction

These products are known as aldols, from the aldehyde + alcohol, a structural motif seen in many of the products. The use of aldehyde in the name comes from its history: aldehydes are more reactive than ketones, so that the reaction was discovered first with them.[2][3][4]

The aldol reaction is paradigmatic in organic chemistry and one of the most common means of forming carbon–carbon bonds in organic chemistry.[5][6][7] It lends its name to the family of aldol reactions and similar techniques analyze a whole family of carbonyl α-substitution reactions, as well as the diketone condensations.

  1. ^ Klein, David R. (December 22, 2020). Organic chemistry (4th ed.). Hoboken, NJ: Wiley. p. 1014. ISBN 978-1-119-65959-4. OCLC 1201694230.
  2. ^ Cite error: The named reference Wurtz1872 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference Wurtz1872b was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Wurtz1872c was invoked but never defined (see the help page).
  5. ^ Wade, L. G. (2005). Organic Chemistry (6th ed.). Upper Saddle River, New Jersey: Prentice Hall. pp. 1056–66. ISBN 978-0-13-236731-8.
  6. ^ Smith, Michael B.; March, Jerry (2006). March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. doi:10.1002/0470084960. ISBN 9780470084960.
  7. ^ Mahrwald, R. (2004). Modern Aldol Reactions, Volumes 1 and 2. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA. pp. 1218–23. ISBN 978-3-527-30714-2.


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