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Chapter 7: PROBLEM 7.71 (page 294)

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

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01

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.
02

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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Most popular questions from this chapter

Question: For each alkyl halide and nucleophile:

[1] Draw the product of nucleophilic substitution.

[2] determine the likely mechanism (or) for each reaction.

a.

b.

c.

d.

Question: (a) Rank A, B, and C in order of increasing SN2 reactivity. (b) Rank A, B, and C in order of increasing SN1 reactivity.

Question: For each reaction, use the identity of the alkyl halide and nucleophile to determine which substitution mechanism occurs. Then determine which solvent affords the faster reaction

a.

b.

c.

Question: Determine the mechanism and draw the products of each reaction. Include the stereochemistry at all stereogenic centers.

a.

b.

c.

d.

Question: Draw the products of each nucleophilic substitution reaction.


b.

c.

d.

e.

f.
See all solutions

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