For the following reaction, the cyanide nucleophile could reasonably substitute at either of two positions. One mechanism produces 4-cyanoheptane and dimethylsulfide. The competing mechanism produces 4-methylthioheptane and acetonitrile (CH3CN). In practice, only one substitution is observed. Choose the most likely mechanistic pathway for this reaction and draw both of the products. Select whether it proceeds via an Sn1 or SN2 mechanism. NaCN

For the following reaction, the cyanide nucleophile could reasonably substitute at either of two positions. One mechanism produces 4-cyanoheptane and dimethylsulfide. The competing mechanism produces 4-methylthioheptane and acetonitrile (CH3CN). In practice, only one substitution is observed. Choose the most likely mechanistic pathway for this reaction and draw both of the products. Select whether it proceeds via an Sn1 or SN2 mechanism. NaCN

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter21: Benzene And The Concept Of Aromaticity

Section: Chapter Questions

Problem 21.64P: Following is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is...

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