PROBLEM 7.20 - Organic Chemistry

Question

Question: Draw the product of each S_N2  reaction and indicate stereochemistry.

a.

b.

   

Step-by-Step Solution

Answer

ANSWER

a.

b.

           

S N 2 reaction

Several reactions form a primary part of organic reactions, and one of those is the  reaction. The reactant stereochemistry influences the reaction product. Hence, these kinds of reactions are known as stereospecific reactions.

Stereochemistry of reaction

The nucleophile can progress from the substrate’s front part or the back part in an reaction. 

When the attack is from the front, the nucleophile and leaving group are on the same side. 

 For attacks launched from the back, the nucleophile does not proceed from the same side to the leaving group. 

 

 

Predicting the product and stereochemistry of reaction

a. In the reaction given below, the breakage of the C-Br bond and the creation of the C-O bond occur at the same time, leading to the generation of the product. 

 

A molecule comprising an S configuration generates a product with an R configuration on the attack of a nucleophile. The product and stereochemistry of the reaction are mentioned below

Product and stereochemistry of question a 

 

b. In the reaction given below, the breakage of the C-I bond and the formation of the C-CN bond occur simultaneously, leading to product formation. 

 On the attack of a nucleophile, the molecule containing an S configuration creates a product comprising an R configuration.

            Product and stereochemistry of question