Q8 P. - Organic Chemistry (Mcmurry)

Question

What product(s) would you expect from reaction of (S)-3-chloro-3-methyloctane with acetic acid? Show the stereochemistry of both reactant and product

Step-by-Step Solution

Answer

Nucleophilic unimolecular substitution reaction S N 1

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 of the reaction of ( S )-3-chloro-3-methyloctane with acetic acid

                                                                       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.