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The ${\mathbf{S}}_{\mathbf{N}}\mathbf{1}$ reaction is a nucleophilic substitution reaction where carbon-halogen bond is broken which results in positively charged carbon and then nucleophile attacks the carbocation and forms a new bond. Only one reacting species is involved in the rate determining step of the reaction. The term${\mathrm{S}}_{\mathrm{N}}1$ stands for substitution nucleophilic unimolecular. The hydrolysis of tert-butyl bromide with aqueous NaOH solution is an example of${\mathrm{S}}_{\mathrm{N}}1$ reaction.

Stereochemistry

In this ${\mathrm{S}}_{\mathrm{N}}1$reaction, attack by acetate can occur on either side of the planar, achiral carbocation intermediate, resulting in a mixture of both the R and S enantiomeric acetates. The ratio of both the enantiomer is probably 50:50.