When the cleavage of an ether occurs, in step 2, how come the bromide ion does not attack the carbon on the cyclopentane? How come it attacks the CH2 carbon? Does it matter which one is being attacked? EXAMPLE: Cleavage of cyclopentyl ethyl ether by HBr.Step 1: Protonation of the ether to form a good leaving group.Ö-CH₂-CH3cyclopentyl ethyl etherStep 2: Cleavage of the protonated ether.HBr-CH₂-CH3H-Br:HاللهH-CH₂-CH3:Br::Br:CH₂ CH3

The cleavage of ether takes place via Substitution Reaction which is of second Order .

MPLE: Cleavage of cyclopentyl ethyl ether by HBr. 1: Protonation of the ether to form a good leaving group. Ö-CH₂-CH3 H-Br: cyclopentyl ethyl ether 2: Cleavage of the protonated ether. H -CH₂-CH3 H J H -Ọ: + -CH₂-CH3 + :Br: CH₂ CH3

MPLE: Cleavage of cyclopentyl ethyl ether by HBr. 1: Protonation of the ether to form a good leaving group. Ö-CH₂-CH3 H-Br: cyclopentyl ethyl ether 2: Cleavage of the protonated ether. H -CH₂-CH3 H J H -Ọ: + -CH₂-CH3 + :Br: CH₂ CH3

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

Chapter8: Haloalkanes, Halogenation, And Radical Reactions

Section: Chapter Questions

Problem 8.28P

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Concept explainers

Amines

Amines are organic compounds with a nitrogen atom having a lone pair of electrons on it. They are derived from ammonia (NH3) wherein hydrogen atoms are substituted by an aryl or alkyl group.

Question

When the cleavage of an ether occurs, in step 2, how come the bromide ion does not attack the carbon on the cyclopentane? How come it attacks the CH2 carbon? Does it matter which one is being attacked?

EXAMPLE: Cleavage of cyclopentyl ethyl ether by HBr.
Step 1: Protonation of the ether to form a good leaving group.
Ö-CH₂-CH3
cyclopentyl ethyl ether
Step 2: Cleavage of the protonated ether.
H
Br
-CH₂-CH3
H
-Br:
H
الله
H
-CH₂-CH3
:Br:
:Br:
CH₂ CH3

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