Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
bartleby

Concept explainers

Question
Book Icon
Chapter 14, Problem 12P

(a)

Interpretation Introduction

Interpretation:

The product of the given reaction should be given.

Concept introduction:

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

Bromination:

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , additional homework tip  1

2-methyl propane undergoes radical bromination which yields the 2-bromo-2-methylpropane.because bromination will occur where the tertiary radical is present.(Bromination reactions are more selective reaction).

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

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

Thus the mechanism of monobromination of ethane is shown below,

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , 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.

Bromination will occur on tertiary radical than the secondary than primary radical, tertiary radical is more stable radical than the other radicals.

(a)

Expert Solution
Check Mark

Answer to Problem 12P

3-methyl hexane undergoes radical bromination and yields the 3-bromo-3-methylhexane which is shown below

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , additional homework tip  3

Explanation of Solution

3-methyl hexane undergoes radical bromination and yields the 3-bromo-3-methylhexane according to the above mentioned mechanism steps. The reaction is shown below,

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , additional homework tip  4

(b)

Interpretation Introduction

Interpretation:

The product of the given reaction should be given.

Concept introduction:

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

Chlorination:

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , additional homework tip  5

2-methyl propane undergoes radical chlorination and yields the 2-bromo-2-methylpropane and 1-bromo-2-methyl propane.

The mechanism of monochlorination of ethane includes three steps,

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

The mechanism of monochlorination of ethane is shown below,

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , additional homework tip  6

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)

Expert Solution
Check Mark

Explanation of Solution

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , additional homework tip  7

Cyclohexane undergoes radical chlorination; all the carbons in cyclohexane are secondary.  Therefore, it yields the 1-chloro cyclohexane according to the above mentioned mechanism steps. And the reaction is shown above.

(c)

Interpretation Introduction

Interpretation:

The product of the given reaction should be given.

Concept introduction:

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

Chlorination:

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , additional homework tip  8

2-methyl propane undergoes radical chlorination and yields the 2-bromo-2-methylpropane and 1-bromo-2-methyl propane.

The mechanism of monochlorination of ethane includes three steps,

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

The mechanism of monochlorination of ethane is shown below,

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , additional homework tip  9

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.

(c)

Expert Solution
Check Mark

Explanation of Solution

Methyl cyclopentane undergoes radical chlorination; the carbons in cyclopentane are secondary and primary.  Therefore, it yields the four types of chlorocyclopentane according to the above mentioned mechanism steps. And the reaction is shown below

Essential Organic Chemistry, Global Edition, Chapter 14, Problem 12P , additional homework tip  10

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Rank the compounds in each group in order of increasing reactivity towards nucleophilic addition a) b) H3C H i H H H3C CH3
Draw a stepwise mechanism showing how two alkylation products are formed in the following reaction.
What is the major alkene formed when A is treated with POCl3 andpyridine? Explain why the major product is different in these reactions.
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning