Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 12, Problem 12.35P
Interpretation Introduction

Interpretation:

The reason for the given order of relative reaction rates of electrophilic addition of Br2 to several alkenes is to be explained.

Concept introduction:

Molecular bromine undergoes anti addition across a C=C double bond. As the electron-rich alkene approaches Br2 molecule, it temporarily generates an electron-poor site on the Br atom closer to the alkene. The subsequent flow of electrons takes place between the electron-rich alkene and the electron-poor Br atom. The presence of an electron donating group attached to the C=C double bond makes it more electron rich which can increase the driving force for the electrophilic addition step.

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Explain why methyl alcohol reacts with HBr faster than other primary alcohols?
H3C CH3 H3C NA C→XT Br Br₂ CH₂Cl₂ H3C Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂. CH3 Br In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br CH3 H3C CH3
Define the Mechanism of the Radical Addition of HBr to an Alkene ?

Chapter 12 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

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