Q3 P. - Organic Chemistry (Mcmurry)

Question

Assign configuration to the following substance, and draw the structure of the product that would result from nucleophilic substitution reaction with  (reddish brown =Br):

Step-by-Step Solution

Answer

Nucleophilic bimolecular substitution reaction S N 2

The reaction is a nucleophilic substitution reaction where bond is broken and another is formed simultaneously. Two reacting species are involved in the rate determining step of the reaction. The term stands for substitution nucleophilic bimolecular.

Inversion of configuration

Inversion of configuration is a process in which the configuration of an atom is changed. If the atom in  question is a stereocenter, inversion of configuration usually changes R absolute configuration  to S, and S into R. Inversion of configuration can also convert cis into trans, or trans into cis.

Show the stereochemistry of both the reactant and product

By identifying the leaving group and chirality center, draw the product carbon skeleton, inverting the configuration at the chirality center, and replace the leaving group (bromide) with the nucleophilic reactant (HS^-). Formation of product of the reactant with its Stereochemistry is shown below.