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PROBLEM 7.71

Expert-verified
Organic Chemistry
Found in: Page 294

Short Answer

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

ANSWER

See the step by step solution

Step by Step Solution

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
  • 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

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