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a. Propose a mechanism for the following reaction: b.

Chapter 13, Problem 37P

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QUESTION:

a. Propose a mechanism for the following reaction:

b. Given that the \(\Delta H^{\circ}\) value for the reaction is \(-42\ \mathrm{kcal} / \mathrm{mol}\) and the bond dissociation energies for the \(\mathrm{C}-\mathrm{H}, \mathrm{C}-\mathrm{Cl}, \text { and } \mathrm{O}-\mathrm{H}\) bonds are \(101,\ 85, \text { and } 105\ \mathrm{kcal} / \mathrm{mol}\) respectively, calculate the bond dissociation energy of the \(O-C l\) bond.

Equation Transcription:

°

Text Transcription:

delta H degree

-42 kcal/mol

C-H, C-Cl, and O-H

101, 85, and 105 kcal/mol

O-Cl

Questions & Answers

QUESTION:

a. Propose a mechanism for the following reaction:

b. Given that the \(\Delta H^{\circ}\) value for the reaction is \(-42\ \mathrm{kcal} / \mathrm{mol}\) and the bond dissociation energies for the \(\mathrm{C}-\mathrm{H}, \mathrm{C}-\mathrm{Cl}, \text { and } \mathrm{O}-\mathrm{H}\) bonds are \(101,\ 85, \text { and } 105\ \mathrm{kcal} / \mathrm{mol}\) respectively, calculate the bond dissociation energy of the \(O-C l\) bond.

Equation Transcription:

°

Text Transcription:

delta H degree

-42 kcal/mol

C-H, C-Cl, and O-H

101, 85, and 105 kcal/mol

O-Cl

ANSWER:

Solution 37P

(a)

Mechanism:

Step 1:

In the first step of the reaction tert-butyl hypochlorite decomposes under thermal condition to generate tert-butyl peroxide. This is the initiation step.

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