Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 9, Problem 9.18P

(a)

Interpretation Introduction

Interpretation:

The alkyl halide has to be selected from the given set of alkyl halides, which shows the greater rate of SN2 reaction with KN3 in acetone.

Concept Introduction:

  • SN2 reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.
  • Better leaving group is good for SN2 reaction because removal of leaving group also be in rate determining step in SN2 reaction.

(b)

Interpretation Introduction

Interpretation:

The alkyl halide has to be selected from the given set of alkyl halides, which shows the greater rate of SN2 reaction with KN3 in acetone.

Concept Introduction:

  • SN2 reaction: It is a nucleophilic substitution reaction in which the rate determining step depends on both alkyl halide and the nucleophile present. The bond making and the bond breaking process happens simultaneously in this reaction, which results in the inversion of configuration.
  • Rate= k[alkylhalide]×[nucleophile]
  • Structure of the substrate plays a major role in SN2 reaction. If the substrate is more substituted the rate of the reaction becomes slower. Since the mechanism of SN2 reaction proceeds through backside attack on the substrate it depends on steric factor of reactant and nucleophile.
  • Polar aprotic solvent is good for SN2 reaction because it is not interact with nucleophile.
  • Less basic good or moderate nucleophile is good for SN2 reaction because it is not abstract a proton only attacks the positive center only.
  • Better leaving group is good for SN2 reaction because removal of leaving group also be in rate determining step in SN2 reaction.

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Chapter 9 Solutions

Organic Chemistry

Ch. 9.9 - Prob. CQCh. 9.9 - Prob. DQCh. 9.10 - Prob. 9.9PCh. 9 - Prob. 9.10PCh. 9 - Prob. 9.11PCh. 9 - Prob. 9.12PCh. 9 - Prob. 9.13PCh. 9 - Prob. 9.14PCh. 9 - Prob. 9.15PCh. 9 - Treatment of 1-aminoadamantane, C10H17N, with...Ch. 9 - Prob. 9.17PCh. 9 - Prob. 9.18PCh. 9 - Prob. 9.19PCh. 9 - Prob. 9.20PCh. 9 - Attempts to prepare optically active iodides by...Ch. 9 - Draw a structural formula for the product of each...Ch. 9 - Prob. 9.23PCh. 9 - Alkenyl halides such as vinyl bromide, CH2=CHBr,...Ch. 9 - Prob. 9.25PCh. 9 - Prob. 9.26PCh. 9 - Prob. 9.27PCh. 9 - Show how you might synthesize the following...Ch. 9 - Prob. 9.29PCh. 9 - 1-Chloro-2-butene undergoes hydrolysis in warm...Ch. 9 - Prob. 9.31PCh. 9 - Prob. 9.32PCh. 9 - Solvolysis of the following bicyclic compound in...Ch. 9 - Which compound in each set undergoes more rapid...Ch. 9 - Prob. 9.35PCh. 9 - Prob. 9.36PCh. 9 - Draw structural formulas for the alkene(s) formed...Ch. 9 - Prob. 9.38PCh. 9 - Following are diastereomers (A) and (B) of...Ch. 9 - Prob. 9.40PCh. 9 - Elimination of HBr from 2-bromonorbornane gives...Ch. 9 - Which isomer of 1-bromo-3-isopropylcyclohexane...Ch. 9 - Prob. 9.43PCh. 9 - Prob. 9.44PCh. 9 - Draw a structural formula for the major organic...Ch. 9 - When cis-4-chlorocyclohexanol is treated with...Ch. 9 - Prob. 9.47PCh. 9 - The Williamson ether synthesis involves treatment...Ch. 9 - The following ethers can, in principle, be...Ch. 9 - Prob. 9.50PCh. 9 - Prob. 9.51PCh. 9 - Prob. 9.52PCh. 9 - Prob. 9.53PCh. 9 - Prob. 9.54PCh. 9 - Write the products of the following sequences of...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.59PCh. 9 - Another important pattern in organic synthesis is...Ch. 9 - Using your reaction roadmap as a guide, show how...Ch. 9 - Prob. 9.62PCh. 9 - Prob. 9.63PCh. 9 - Prob. 9.64P
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