Keto-Enol Tautomerism
An extensive introduction to keto-enol tautomerism in aldehydes and ketones, with mechanisms, quizzes, key concepts, references and more.
Read moreEnols and Enolates
Enolates – Formation, Stability, and Simple Reactions
All about enolates Enolates can be formed through removing the proton on carbons adjacent to a carbonyl (i.e. the “alpha-carbon“). The resulting anions are much
Read moreKinetic Versus Thermodynamic Enolates
Kinetic versus Thermodynamic Enolates of Ketones Enolates have a lot in common with alkenes. They are flat and have a C-C pi bond. Zaitsev’s rule
Read moreAldol Addition and Condensation Reactions
Aldol Addition and Condensation Reactions (Base-Catalyzed) The Aldol Addition reaction is the addition of an enolate to an aldehyde (or ketone). Heating with base can result
Read moreReactions of Enols – Acid-Catalyzed Aldol, Halogenation, and Mannich Reactions
Reactions of Enols – Aldol Condensation, Halogenation, Mannich Reaction In a previous post on keto-enol tautomerism, we described the keto and enol forms. In this
Read moreClaisen Condensation and Dieckmann Condensation
The Claisen Condensation (And Its Intramolecular Version, The “Dieckmann” Condensation) The Claisen condensation is one of the fundamental reactions of esters. In the Claisen condensation,
Read moreDecarboxylation
Decarboxylation In this article we’ll cover decarboxylation, most commonly encountered in the context of the loss of CO2 from beta-keto acids (and malonic acids) in the
Read moreThe Malonic Ester and Acetoacetic Ester Synthesis
The Malonic Ester Synthesis And Its Cousin, The Acetoacetic Ester Synthesis In the malonic ester synthesis, a di-ester of malonic acid is deprotonated with a
Read moreThe Michael Addition Reaction and Conjugate Addition
The Michael Addition Reaction (and Conjugate Addition) The Michael reaction (sometimes “Michael Addition”) is the addition of an enolate to an electrophilic alkene, such as
Read moreThe Robinson Annulation
The Robinson Annulation The Robinson Annulation is the name for a process that combines two key reactions you’ve learned previously into one longer sequence. The
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