(S)-3-Chloro-1-pentene reacts with sodium ethoxide in ethanol to produce 3-ethoxy-1-pentene. The reaction is second order, first order in 3-chloro-1-pentene and first order in sodium ethoxide. In the absence of sodium ethoxide, 3-chloro-1-pentene reacts with ethanol to produce both 1-ethoxy-2-pentene and 3-ethoxy-1-pentene. The first reaction proceeds via an Sn2 mechanism. The stereochemistry of the product is R The second reaction proceeds via an Sy1 mechanism. The stereochemistry of 1-ethoxy-2-pentene is none The stereochemistry of 3-ethoxy-1-pentene is racemic

(S)-3-Chloro-1-pentene reacts with sodium ethoxide in ethanol to produce 3-ethoxy-1-pentene. The reaction is second order, first order in 3-chloro-1-pentene and first order in sodium ethoxide. In the absence of sodium ethoxide, 3-chloro-1-pentene reacts with ethanol to produce both 1-ethoxy-2-pentene and 3-ethoxy-1-pentene. The first reaction proceeds via an Sn2 mechanism. The stereochemistry of the product is R The second reaction proceeds via an Sy1 mechanism. The stereochemistry of 1-ethoxy-2-pentene is none The stereochemistry of 3-ethoxy-1-pentene is racemic

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

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.15P

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