Q47cE - Organic Chemistry (Mcmurry)

Question

Question: Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles with (R)-2-bromooctane: 

(c) $C{H}_3{S}^{-}$

Step-by-Step Solution

Answer

Answer

Step 1: S N 2 reaction

This is a nucleophilic substitution reaction in which an old bond is broken and a new bond is formed simultaneously. The response is one-step because there is only one bond to form.

The two reacting species are involved in the rate-determining steps.

Step 2: Definition of Nucleophiles and Stereochemistry

Nucleophiles are the negatively charged ions or the neutral species having the lone pair of electrons ready for bonding.

Stereochemistry - It is a study of the arrangement of atoms in a space that forms a molecule 

Step 3: Species react faster with 2-Bromoctane

2-bromoctane is a secondary bromoalkane, so the reaction proceeds with the inversion of configuration that the chirality of the carbon atom is changed as shown: