Q47aE - 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: 

a)  $C{N}^{-}$

Step-by-Step Solution

Answer

Answer

Step 1: S N 2 reaction

It is a nucleophilic substitution reaction in which an old bond is broken and a new bond has formed both processes occur simultaneously. Hence, it’s a single-step reaction.

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

Step 2: Definition of Nucleophile and Stereochemistry

Nucleophiles are the negatively charged ions or the neutral species having the lone pair of electrons that are 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: