Identify the cyclohexyl substrate which would undergo the fastest E2 with base.

Fundamentals Of Analytical Chemistry
9th Edition
ISBN:9781285640686
Author:Skoog
Publisher:Skoog
Chapter30: Kinetic Methods Of Analysis
Section: Chapter Questions
Problem 30.2QAP
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Identify the cyclohexyl substrate which would undergo the fastest E2 with base.

CI
OTos
Br
CI
A
B
D
Transcribed Image Text:CI OTos Br CI A B D
Expert Solution
Step 1
  • E2 elimination is a one step concerted mechanism reaction in which dehydrohalogenation (or any other leaving group) occurs to yield the corresponding alkene. 
  • It is a bimolecular reaction. It is a second order reaction.
  • The bond anti- to Carbon-halogen (or any other leaving group) migrates so as to give the elimination product. 
Step 2

The anti- bonds in the given molecules A-D are:

Chemistry homework question answer, step 2, image 1

  • In molecules B and C, the anti- bond cannot assist the elimination reaction as the hydrogen is not trans- to leaving group. 
  • In molecules A and D, the hydrogen is trans- to leaving group, so they will show fast elimination. 
  • Among A and D, as -OTs in D is a better leaving group, so the reaction will be fastest. 
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