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: 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, (i) Initiation (ii) Propagation (iii) Termination Thus the mechanism of monobromination of ethane is shown below, 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.

Question

Want to see more full solutions like this?

Answer 1

Question

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

Thus the mechanism of monobromination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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

Choose the best reagents to complete the reaction shown below. L a

Draw the major organic product when this compound is treated with NBS and heat: H3C -CH3

Answer 2

Question

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

Thus the mechanism of monobromination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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!

Answer 3

Question

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

Thus the mechanism of monobromination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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!

Answer 4

Question

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

Thus the mechanism of monobromination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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!

Answer 5

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

Thus the mechanism of monobromination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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

Answer 6

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

Thus the mechanism of monobromination of ethane is shown below,

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

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

Answer 7

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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

Thus the mechanism of monobromination of ethane is shown below,

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.

Answer 8

(a)

Expert Solution

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

Answer 9

(a)

Expert Solution

Answer 10

(a)

Expert Solution

Answer 11

Expert Solution

Answer 12

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

Answer 13

(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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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.

Answer 14

(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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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.

Answer 15

(b)

Expert Solution

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.

Answer 16

(b)

Expert Solution

Answer 17

(b)

Expert Solution

Answer 18

Expert Solution

Answer 19

(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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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

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

Answer 20

(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:

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,

(i) Initiation

(ii) Propagation

(iii) Termination

The mechanism of monochlorination of ethane is shown below,

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.

Answer 21

(c)

Expert Solution

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