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Chapter 7: PROBLEM 7.71 (page 294)

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

Short Answer

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Step by step solution

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掳>2掳>3掳
  • The rate of the reaction is 2.
02

Mechanism

The reaction鈥檚 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: Draw the products of each nucleophilic substitution reaction.


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Question: When (R)-6-bromo-2,6-dimethylnonane is dissolved in , nucleophilic substitution yields an optically inactive solution. When the isomeric halide (R)-2-bromo-2,5- dimethylnonane is dissolved in under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.

Question: Explain why quinuclidine is a much more reactive nucleophile than triethylamine, even though both compounds have N atoms surrounded by three R groups.
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