PROBLEM 7.71 - Organic Chemistry

Question

Question: Draw a stepwise, detailed mechanism for the following reaction.

Step-by-Step Solution

Answer

ANSWER

Bimolecular substitution reactions

The bimolecular substitution reaction is the part of the substitution reaction in which the strong nucleophile attacks the leaving group center. 

The following points are shown:

• The bimolecular substitution reaction follows the substrate order as $1°>2°>3°$

• The rate of the reaction is 2.  

Mechanism

The reaction’s substrate has two chloride groups. So, the nucleophile (methylamine) attacks the carbon bearing the chloride bond (C-Cl). Since the chloride ion is a good leaving group, the methylamine is substituted at the place of Cl. 

 The substrate now has one Cl remaining; the substituted methylamine attacks the other carbon (C-Cl) and forms intramolecular bonding. The methylamine cyclizes after leaving the chloride ion and forms the final product with a salt (by-product).

Representation of reaction mechanism