Question

Question: If the reaction of an alcohol with SOCl₂and pyridine follows an S_N2 mechanism, what is the stereochemistry of the alkyl chloride formed from (R)-butan-2-ol?

Short answer

Answer

The stereochemistry of the alkyl chloride formed from (R)-butan-2-ol is (S)-2-chlorobutane.

Step-by-step solution

Step-by-Step Solution Step 1: Reaction of alcohol

The reaction of alcohol with thionyl chloride in the presence of pyridine results in the formation of alkyl halide. This reaction is followed by an reaction and yields the inversion of the configuration.

Formation of the product

The reaction of (R)-butan-2-ol with ${\mathrm{SOCl}}_2$in the presence of pyridine undergoes the ${\mathrm{S}}_{\mathrm{N}}2$ mechanism and forms the inversion of the configuration, which means that (S)-2-chlorobutane is formed.

The reaction is shown below.

Formation of alkyl halide