Organic Chemistry Plus Mastering Chemistry with Pearson eText -- Access Card Package (9th Edition) (New in Organic Chemistry)

9th Edition

ISBN: 9780321971128

Author: Leroy G. Wade, Jan W. Simek

Publisher: PEARSON

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Textbook Question

Chapter 4, Problem 4.58SP

lodination of alkanes using iodine (I₂) is usually an unfavorable reaction. (See Problem4-17, for example.) Tetraiodomethane (Cl₄) can be used as the iodine source for iodination in the presence of a free-radical initiator such as hydrogen peroxide. Propose a mechanism (involving mildly exothermic propagation steps) for the following proposed reaction. Calculate the value of ∆H for each of the steps in your proposed mechanism.

Chapter 4, Problem 4.58SP, lodination of alkanes using iodine (I2) is usually an unfavorable reaction. (See Problem4-17, for , example 1

The following bond-dissociation energies may be helpful:

Chapter 4, Problem 4.58SP, lodination of alkanes using iodine (I2) is usually an unfavorable reaction. (See Problem4-17, for , example 2

Formula Formula Bond dissociation energy (BDE) is the energy required to break a bond, making it an endothermic process. BDE is calculated for a particular bond and therefore consists of fragments such as radicals since it undergoes homolytic bond cleavage. For the homolysis of a X-Y molecule, the energy of bond dissociation is calculated as the difference in the total enthalpy of formation for the reactants and products. X-Y → X + Y BDE = Δ H f X + Δ H f Y – Δ H f X-Y where, ΔHf is the heat of formation.

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Chapter 4, Problem 4.57SP

Chapter 5.2, Problem 5.1P

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Chapter 4 Solutions

Organic Chemistry Plus Mastering Chemistry with Pearson eText -- Access Card Package (9th Edition) (New in Organic Chemistry)

Ch. 4.3A - Draw Lewis structures for the following free...Ch. 4.3B - a. Write the propagation steps leading to the...Ch. 4.3C - Prob. 4.3P Ch. 4.3C - Prob. 4.4P Ch. 4.4 - The following reaction has a value of G =...Ch. 4.4 - Under base-catalyzed conditions two molecules of...Ch. 4.5B - When ethene is mixed with hydrogen in the presence...Ch. 4.5B - For each reaction, estimate whether S for the...Ch. 4.7 - a. Propose a mechanism for the free radical...Ch. 4.7 - a. Using bond-dissociation enthalpies from...

Ch. 4.8 - The reaction of tert-butyl chloride with methanol...Ch. 4.8 - Under certain conditions, the bromination of...Ch. 4.8 - When a small piece of plat num is added to a...Ch. 4.10 - Prob. 4.14P Ch. 4.10 - Prob. 4.15P Ch. 4.12 - The bromination of methane proceeds through the...Ch. 4.12 - a. Using me BDEs in Table4-2 (page 167 ), compute...Ch. 4.13A - What would be the product ratio in the...Ch. 4.13A - Classify each hydrogen atom in the following...Ch. 4.13B - Use the bond-dissociation enthalpies in Tabte4-2...Ch. 4.13B - Prob. 4.21P Ch. 4.13B - Prob. 4.22P Ch. 4.14 - a. Compute the heats of reaction for abstraction...Ch. 4.14 - 2,3-Dimethylbutane reacts with bromine in the...Ch. 4.14 - Prob. 4.25P Ch. 4.15 - Prob. 4.26P Ch. 4.15 - Prob. 4.27P Ch. 4.16A - Prob. 4.28P Ch. 4.16A - Prob. 4.29P Ch. 4.16B - Prob. 4.30P Ch. 4.16C - Prob. 4.31P Ch. 4.16C - Acetonitrile (CH3C N) is deprotonated by very...Ch. 4.16D - Prob. 4.33P Ch. 4 - The following reaction is a common synthesis used...Ch. 4 - Consider the following reaction-energy diagram. a....Ch. 4 - Draw a reaction-energy diagram for a one-step...Ch. 4 - Draw a reaction-energy diagram for a two-step...Ch. 4 - Prob. 4.38SP Ch. 4 - Treatment of tert-butyl alcohol with concentrated...Ch. 4 - Label each hydrogen atom in the following...Ch. 4 - Prob. 4.41SP Ch. 4 - Prob. 4.42SP Ch. 4 - Prob. 4.43SP Ch. 4 - Prob. 4.44SP Ch. 4 - Prob. 4.45SP Ch. 4 - Prob. 4.46SP Ch. 4 - For each compound, predict the major product of...Ch. 4 - When exactly 1 mole of methane is mixed with...Ch. 4 - Prob. 4.49SP Ch. 4 - Prob. 4.50SP Ch. 4 - Prob. 4.51SP Ch. 4 - When dichloromethane is treated with strong NaOH,...Ch. 4 - Prob. 4.53SP Ch. 4 - When a small amount of iodine is added to a...Ch. 4 - Prob. 4.55SP Ch. 4 - When healthy, Earths stratosphere contains a low...Ch. 4 - Prob. 4.57SP Ch. 4 - lodination of alkanes using iodine (I2) is usually...

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Solution Summary: The author proposes a mechanism for the given reaction and calculates the value of Delta H for each of the steps.

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