Organic Chemistry - Chapter 21 Alpha Carbon Chemistry

This deck consists of vocabulary terms related to alpha carbon chemistry, specifically enols and enolates, sourced from Chapter 21 of Organic Chemistry.

Alpha Carbon

The carbon atom adjacent to a carbonyl group.

Enol

An alkene with a hydroxyl group, in equilibrium with its carbonyl form.

Enolate

A negatively charged species formed by deprotonation of an enol.

Tautomerization

The process of interconversion between two isomers, such as a ketone and an enol.

Aldol Addition

A reaction where an enolate attacks a carbonyl compound to form a beta-hydroxy carbonyl.

Claisen Condensation

A carbon-carbon bond formation reaction involving the reaction of two esters or an ester and a carbonyl compound to form a beta-keto ester.

Haloform Reaction

A reaction where methyl ketones are converted to carboxylic acids using halogen and base.

Michael Reaction

A nucleophilic addition of stabilized enolates to beta positions of alpha, beta-unsaturated carbonyls.

Decarboxylation

The removal of a carboxyl group from a carboxylic acid, releasing carbon dioxide.

LDA (Lithium diisopropylamide)

A strong base used to irreversibly form enolates in organic reactions.

Alpha Halogenation

The reaction of alpha protons in carbonyl compounds with halogens under acidic or basic conditions.

Regioselectivity

The preference of one direction of a chemical reaction over all other possible directions.

Directed Aldol Addition

A strategy to minimize products in a crossed aldol reaction by selectively converting one compound to an enolate.

Enamine

A derivative of an amine formed by the reaction of an aldehyde or ketone with a secondary amine.

Robinson Annulation

A two-step process consisting of Michael addition followed by an intramolecular aldol condensation.

Stabilized Enolate

An enolate that can distribute negative charge across multiple resonance forms, favoring conjugate addition.

1,3-Dicarbonyl Compounds

Organic compounds containing two carbonyl groups separated by one carbon.

Kinetic vs. Thermodynamic Enolate

Kinetic enolates are formed at low temperatures and favor quicker reactions, while thermodynamic enolates are formed at higher temperatures and favor stability.