ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
2nd Edition
ISBN: 9780393664034
Author: KARTY
Publisher: NORTON
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Chapter 11, Problem 11.56P
Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the reaction of but-1-ene-3-yne with HBr, producing 4-bromobuta-1, 2-diene is to be drawn.

Concept introduction:

The pi bond of an alkene or an alkyne is an electron-rich region. It undergoes electrophilic addition reaction when treated with a Bronsted acid. The addition of proton in the first step leads to the formation of a carbocation intermediate. The carbocation may undergo a rearrangement if it leads to a more stable carbocation. In the second step, the conjugate base of the acid adds to the carbocation.

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Chapter 11 Solutions

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