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](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fc6d45b7c-770b-4dbe-b3cf-74fe1dfded8d%2F0ea03617-2593-41f1-83ba-2f97c12a1671%2F89kakso_processed.png&w=3840&q=75)
Transcribed Image Text:CI
OTos
Br
CI
A
B
D
Expert Solution
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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:
- 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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