The Wurtz coupling uses sodium metal and two alkyl halides to make a new carbon-carbon bond. First, a metal-halogen exchange forms a carbanion that then attacks the second alkyl halide in SN2 fashion. Reagents: Sodium Metal, Solvent (THF, Et2O, Dioxane, Xylenes) Reactant: Alkyl Halide Product: Alkane Type of Reaction: Metal-Catalyzed...

The Yamaguchi Esterification converts a Carboxylic Acid to an Ester. First, Triethylamine (Et3N) deprotonates the Carboxylic Acid, which then attacks the Yamaguchi reagent (2,4,6-Trichlorobenzoyl chloride) to produce an acid anhydride. The Yamaguchi reagent is released when the acid anhydride is attacked by 4-dimethylaminopyridine (DMAP). The alcohol displaces DMAP and a...

The Biginelli reaction is a one-pot (three-component) procedure that in the presence of an acid catalyst, converts a β-keto ester, an aryl aldehyde, and urea to a hexahydropyrimidine derivative. First, urea reacts with the aldehyde affording an aminal, which dehydrates to an N-acyliminium ion. The enol form of the β-keto...

The Dakin-West reaction uses a base to convert an amino acid and anhydride to an acylamino ketone. Acylation of both the nitrogen atom and the carboxylic acid group occur first, followed by an intramolecular acyl substitution, producing a protonated oxazolone intermediate. Further acylation of the oxazolone, acetoxy group additions, and...

The intramolecular condensation of a diester, producing a cyclic β-keto ester, is called the Dieckmann condensation. The base abstracts an α-proton from one of the esters, yielding an enolate ion that attacks the other ester, forming a tetrahedral intermediate. Alkoxide ion is released, followed by the formation of a second...

Proceeding through a concerted, aromatic transition state, the Diels-Alder [4π+2π] cycloaddition uses heat to form a cyclohexene derivative from an electron rich (s-cis) diene and an electron poor dienophile (referred to as the normal electron-demand Diels-Alder reaction). Benefits include the conservation of the starting dienophile’s stereochemistry and the high regioselectivity...