Consider the following reaction. CH3 CH3 CH;CH,-C-OH + HBr CH3CH2-C-Br CH3 CH3 (i) By which of the two mechanisms (SN1 or SN2) does the reaction proceeds? (ii) Provide a detailed mechanism for the reaction.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...
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The conversion of alcohols into alkyl halides by reaction with hydrogen halides is an example of a Nucleophilic Substitution Reaction. This kind of reaction can proceed by two different mechanisms depending on the structure of alcohol substrates used. Generally, primary alcohols are substituted via SN2 mechanism, while secondary and tertiary alcohols undergo SN1 mechanism.

Consider the following reaction given in the picture below and the questions in the picture too. 

 

Consider the following reaction.
CH3
CH
CH;CH,-C-OH +
HBr
CH;CH2-Ċ-Br
CH
CH3
(i) By which of the two mechanisms (Sy1 or Sy2) does the reaction proceeds?
(ii) Provide a detailed mechanism for the reaction.
I
Transcribed Image Text:Consider the following reaction. CH3 CH CH;CH,-C-OH + HBr CH;CH2-Ċ-Br CH CH3 (i) By which of the two mechanisms (Sy1 or Sy2) does the reaction proceeds? (ii) Provide a detailed mechanism for the reaction. I
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