Physics

Organic chemistry

Solvent polarity

Hydrolysis

Catalysis

Nucleophile

Computational chemistry

Medicinal chemistry

Component (thermodynamics)

Chemistry

Bromide

Solvent

Solvolysis

Ethanol

SN2 reaction

Thermodynamics

Journal of the Chemical Society. Perkin transactions II

The solvolysis of but-3-enyl bromide at 70 °C follows the SN2 mechanism over a wide variety of solvent as indicated by a sensitivity to changes in solvent nucleophilicity (l value) of 0.99 ± 0.04, specific rates of solvolysis of about on-half of those for the saturated butyl bromide and a kOTs/kBr ratio in ethanol of 12, essentially indentical with the value previously observed for ethanolyses of methyl and ethyl derivatives. There are indications of a minor (about 35%) SN1 component to the solvolysis in 97% TFE, which becomes dominant in 90% HFIP. Kinetic analysis suggest, consistent with previous product studies, only an approximately 4% SN2 component to a dominant SN1 formolysis of the corresponding tosylate.

A study of the mechanism of solvoysis of but-3-enyl bromide (4-bromobut-1-ene) using the extended (two-term) Grunwald–Winstein equation