The Williamson ether synthesis is an SN2 reaction The Williamson ether synthesis uses a base and an alkyl halide to convert an alcohol into a symmetrical or an unsymmetrical ether. The base deprotonates the alcohol to form an alkoxide that undergoes a nucleophilic substitution (SN2) reaction with the alkyl halide,...

The Wittig reaction uses triphenylphosphine (PPh3), a base, and a 1° or 2° alkyl halide to convert an aldehyde or ketone to an olefin. First a phosphonium salt is made when the PPh3 attacks the alkyl halide, releasing a halide ion in the process. The α-hydrogen is then deprotonated by...

The Wolff-Kishner reduction uses hydrazine, a base, and a high-boiling solvent to convert an aldehyde or ketone to an alkane. The hydrazine first attacks the ketone or aldehyde, releasing water to form a hydrazone intermediate. Subsequent proton transfer steps result in the release of nitrogen gas and the formation of...

The Wolff rearrangement uses either catalytic silver oxide, heat, or light to convert an α-diazo ketone to a ketene. In a one-step reaction, the catalyst initiates a 1,2-shift to release nitrogen gas and produce ketene. Due to the release of nitrogen gas, this reaction should not be performed in a...

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...