Why would concentrated HBr be an inappropriate catalyst for the dehydration of alcohols?The conjugate base Br- is a good nucleophile and would attack the carbocation to form an alkyl bromideO HBr is strongly acidic, so the water molecule would not be a good leaving group after alcohol protonation.O HBr would be more likely to promote rearrangement of the carbocation intermediateHBr is too weakly acidic to protonate alcohols

Alcohols upon dehydration to give alkenes It is an example for elimination reactions Generally…

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Why would concentrated HBr be an inappropriate catalyst for the dehydration of alcohols?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter13: Substitution

Section: Chapter Questions

Problem 26E

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Question

Why would concentrated HBr be an inappropriate catalyst for the dehydration of alcohols?
The conjugate base Br- is a good nucleophile and would attack the carbocation to form an alkyl bromide
O HBr is strongly acidic, so the water molecule would not be a good leaving group after alcohol protonation.
O HBr would be more likely to promote rearrangement of the carbocation intermediate
HBr is too weakly acidic to protonate alcohols

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