EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
2nd Edition
ISBN: 9780393630817
Author: KARTY
Publisher: W.W.NORTON+CO. (CC)
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Question
Chapter 12, Problem 12.35P
Interpretation Introduction
Interpretation:
The reason for the given order of relative reaction rates of electrophilic addition of
Concept introduction:
Molecular bromine undergoes anti addition across a
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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
The relative rates of reaction of ethane, toluene, and ethylbenzene with bromine atoms have
been measured. The most reactive hydrocarbon undergoes hydrogen atom abstraction a million times
faster than does the least reactive one. Arrange these hydrocarbons order of decreasing reactivity.
Define the Mechanism of the Radical Addition of HBr to an Alkene ?
Chapter 12 Solutions
EBK ORGANIC CHEMISTRY: PRINCIPLES AND M
Ch. 12 - Prob. 12.1PCh. 12 - Prob. 12.2PCh. 12 - Prob. 12.3PCh. 12 - Prob. 12.4PCh. 12 - Prob. 12.5PCh. 12 - Prob. 12.6PCh. 12 - Prob. 12.7PCh. 12 - Prob. 12.8PCh. 12 - Prob. 12.9PCh. 12 - Prob. 12.10P
Ch. 12 - Prob. 12.11PCh. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Prob. 12.14PCh. 12 - Prob. 12.15PCh. 12 - Prob. 12.16PCh. 12 - Prob. 12.17PCh. 12 - Prob. 12.18PCh. 12 - Prob. 12.19PCh. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Prob. 12.22PCh. 12 - Prob. 12.23PCh. 12 - Prob. 12.24PCh. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Prob. 12.27PCh. 12 - Prob. 12.28PCh. 12 - Prob. 12.29PCh. 12 - Prob. 12.30PCh. 12 - Prob. 12.31PCh. 12 - Prob. 12.32PCh. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - Prob. 12.37PCh. 12 - Prob. 12.38PCh. 12 - Prob. 12.39PCh. 12 - Prob. 12.40PCh. 12 - Prob. 12.41PCh. 12 - Prob. 12.42PCh. 12 - Prob. 12.43PCh. 12 - Prob. 12.44PCh. 12 - Prob. 12.45PCh. 12 - Prob. 12.46PCh. 12 - Prob. 12.47PCh. 12 - Prob. 12.48PCh. 12 - Prob. 12.49PCh. 12 - Prob. 12.50PCh. 12 - Prob. 12.51PCh. 12 - Prob. 12.52PCh. 12 - Prob. 12.53PCh. 12 - Prob. 12.54PCh. 12 - Prob. 12.55PCh. 12 - Prob. 12.56PCh. 12 - Prob. 12.57PCh. 12 - Prob. 12.58PCh. 12 - Prob. 12.59PCh. 12 - Prob. 12.60PCh. 12 - Prob. 12.61PCh. 12 - Prob. 12.62PCh. 12 - Prob. 12.63PCh. 12 - Prob. 12.64PCh. 12 - Prob. 12.1YTCh. 12 - Prob. 12.2YTCh. 12 - Prob. 12.3YTCh. 12 - Prob. 12.4YTCh. 12 - Prob. 12.5YTCh. 12 - Prob. 12.6YTCh. 12 - Prob. 12.7YTCh. 12 - Prob. 12.8YTCh. 12 - Prob. 12.9YTCh. 12 - Prob. 12.10YTCh. 12 - Prob. 12.11YTCh. 12 - Prob. 12.12YT
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