EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 9781319188962
Author: VOLLHARDT
Publisher: VST
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Chapter 3, Problem 25P
Interpretation Introduction

Interpretation:Potential-energy/reaction-coordinate diagrams for the two propagation steps of the radical bromination of benzene should be sketched.

Concept introduction: Analogous to hydrocarbons the benzene can also undergo initiation to generate bromine radicals; propagation of radicals formed and finally termination. This sequence can be outlined as follows:

Step1: Initiation via homolytic cleavage of BrBr bond: Br2 initiates the reaction; undergoes homolysis and forms bromine radical atom. Energy for homolytic cleavage is provided by the heat or ultraviolet light.

  EBK ORGANIC CHEMISTRY, Chapter 3, Problem 25P , additional homework tip  1

Step2: Propagation: In first of the propagation steps, bromine radical from step 1 abstracts hydrogen radical from C6H6 as follows:

  EBK ORGANIC CHEMISTRY, Chapter 3, Problem 25P , additional homework tip  2

In subsequent propagation step,phenyl radical abstracts Br· radical from another Br2 , and liberates bromobenzene and new bromine radical.

  EBK ORGANIC CHEMISTRY, Chapter 3, Problem 25P , additional homework tip  3

Step3: Termination: Bromine radicals generated in propagation steps get quenched upon combination with one another illustrated as follows:

  EBK ORGANIC CHEMISTRY, Chapter 3, Problem 25P , additional homework tip  4

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When an unknown amine reacts with an unknown acid chloride, an amide with a molecular mass of 163 g/mol (M* = 163 m/z) is formed. In the infrared spectrum, important absorptions appear at 1661, 750 and 690 cm. The 13C NMR and DEPT spectra are provided. Draw the structure of the product as the resonance contributor lacking any formal charges. 13C NMR DEPT 90 200 160 120 80 40 0 200 160 120 80 40 0 DEPT 135 T 200 160 120 80 40 0 Draw the unknown amide. Select Dow Templates More Frage
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