Related Experiment Video
Updated: Apr 26, 2026

Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
Published on: February 20, 2020
The Lewis base-catalyzed silylation of alcohols--a mechanistic analysis
Pascal Patschinski1, Cong Zhang, Hendrik Zipse
1Department of Chemistry, Ludwig-Maximilians-Universität , 81377 München, Germany.
Abstract:
Reaction rates for the base-catalyzed silylation of primary, secondary, and tertiary alcohols depend strongly on the choice of solvent and catalyst. The reactions are significantly faster in Lewis basic solvents such as dimethylformamide (DMF) compared with those in chloroform or dichloromethane (DCM). In DMF as the solvent, the reaction half-lives for the conversion of structurally similar primary, secondary, and tertiary alcohols vary in the ratio 404345:20232:1. The effects of added Lewis base catalysts such as 4-N,N-dimethylaminopyridine (DMAP) or 4-pyrrolidinopyridine (PPY) are much larger in apolar solvents than in DMF. The presence of an auxiliary base such as triethylamine is required in order to drive the reaction to full conversion.
Related Concept Videos
Conversion of Alcohols to Alkyl Halides
α-Alkylation of Ketones via Enolate Ions
Base-Catalyzed Aldol Addition Reaction
Acid Halides to Esters: Alcoholysis
Preparation of Alcohols via Addition Reactions
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
Crossed Aldol Reaction Using Strong Bases: Directed Aldol Reaction

