Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
Question
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Chapter 14, Problem 17P

(a)

Interpretation Introduction

Interpretation:

The numbers of chlorination products obtained from radical chlorination of methyl cyclohexane has to be given.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

In a halogenation reaction, one or more halogen atoms are introduced into an organic compound. Generally, these reactions are initiated in the presence of light or heat.

Chlorination:

Essential Organic Chemistry (3rd Edition), Chapter 14, Problem 17P , additional homework tip  1

2-methylpropane undergoes radical chlorination which yields the 2-chloro-2-methylpropane and 1-chloro-2-methylpropane.

The mechanism of monochlorination of ethane (as an example) includes three steps,

  1. (i) Initiation
  2. (ii) Propagation
  3. (iii) Termination

The mechanism of monochlorination of ethane is shown below,

Essential Organic Chemistry (3rd Edition), Chapter 14, Problem 17P , additional homework tip  2

In a halogenation reaction, one or more halogen atoms are introduced into an organic compound. Generally, these reactions are initiated in the presence of light or heat

(b)

Interpretation Introduction

Interpretation:

The number of monochlorination products obtained from the radical chlorination of methyl cyclohexane should be given when all stereoisomers are included.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

In a halogenation reaction, one or more halogen atoms are introduced into an organic compound. Generally, these reactions are initiated in the presence of light or heat.

Chlorination:

Essential Organic Chemistry (3rd Edition), Chapter 14, Problem 17P , additional homework tip  3

2-methylpropane undergoes radical chlorination which yields the 2-chloro-2-methylpropane and 1-chloro-2-methylpropane.

The mechanism of monochlorination of ethane (as an example) includes three steps,

  1. (i) Initiation
  2. (ii) Propagation
  3. (iii) Termination

The mechanism of monochlorination of ethane is shown below,

Essential Organic Chemistry (3rd Edition), Chapter 14, Problem 17P , additional homework tip  4

In a halogenation reaction, one or more halogen atoms are introduced into an organic compound. Generally, these reactions are initiated in the presence of light or heat

Chiral: Four different atoms attached to a carbon atom is called chiral molecule.

Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.

Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.

Diastereomers: A compound which is non-superimposable and non-mirror image is called enantiomers

Total number of stereoisomers = 2n

Where n is the number of chiral centers.

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