The structural formula of the most stable cyclohexadienyl cation intermediate formed in each of the given reactions is to be written. Whether this carbocation is more or less stable than the cyclohexadienyl intermediate formed by benzene, is to be determined. Concept Introduction: Compounds containing benzene ring undergo electrophilic aromatic substitution reaction with electrophilic reagents. The mechanism of electrophilic aromatic substitution involves two steps. In the first step, an electrophile accepts an electron pair from pi system of benzene giving an intermediate called as cyclohexadienyl cation or arenium ion intermediate. In the second step, the cyclohexadienyl cation intermediate undergoes deprotonation to restore the aromaticity of benzene ring. In order to form cyclohexadienyl cation intermediate, the electrophile must be reactive. Electron donating substituents present on the benzene ring increase the reactivity towards the electrophilic aromatic substitution reactions by stabilizing the cyclohexadienyl cation intermediate. When an electron donating substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be more stable than the cyclohexadienyl intermediate formed by benzene. When an electron withdrawing substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be less stable than the cyclohexadienyl intermediate formed by benzene. Stability of a cyclohexadienyl cation intermediate depends mainly on two factors – its proximity to an electron donating or electron withdrawing group and whether it is an allylic carbocation or not.

Question

Want to see the full answer?

Answer 1

Question

Chapter 13, Problem 55P

Interpretation Introduction

Interpretation:

The structural formula of the most stable cyclohexadienyl cation intermediate formed in each of the given reactions is to be written. Whether this carbocation is more or less stable than the cyclohexadienyl intermediate formed by benzene, is to be determined.

Concept Introduction:

Compounds containing benzene ring undergo electrophilic aromatic substitution reaction with electrophilic reagents.

The mechanism of electrophilic aromatic substitution involves two steps.

In the first step, an electrophile accepts an electron pair from pi system of benzene giving an intermediate called as cyclohexadienyl cation or arenium ion intermediate.

In the second step, the cyclohexadienyl cation intermediate undergoes deprotonation to restore the aromaticity of benzene ring.

In order to form cyclohexadienyl cation intermediate, the electrophile must be reactive.

Electron donating substituents present on the benzene ring increase the reactivity towards the electrophilic aromatic substitution reactions by stabilizing the cyclohexadienyl cation intermediate.

When an electron donating substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be more stable than the cyclohexadienyl intermediate formed by benzene.

When an electron withdrawing substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be less stable than the cyclohexadienyl intermediate formed by benzene.

Stability of a cyclohexadienyl cation intermediate depends mainly on two factors – its proximity to an electron donating or electron withdrawing group and whether it is an allylic carbocation or not.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

What is the molarity of a 0.393 m glucose solution if its density is 1.16 g/mL? MM glucose 180.2 g/mol

The rate constant for the decay of a radioactive element is 2.28 × 10⁻³ day⁻¹. What is the half-life of this element in days?

Handwritten please

Answer 2

Question

Chapter 13, Problem 55P

Interpretation Introduction

Interpretation:

The structural formula of the most stable cyclohexadienyl cation intermediate formed in each of the given reactions is to be written. Whether this carbocation is more or less stable than the cyclohexadienyl intermediate formed by benzene, is to be determined.

Concept Introduction:

Compounds containing benzene ring undergo electrophilic aromatic substitution reaction with electrophilic reagents.

The mechanism of electrophilic aromatic substitution involves two steps.

In the first step, an electrophile accepts an electron pair from pi system of benzene giving an intermediate called as cyclohexadienyl cation or arenium ion intermediate.

In the second step, the cyclohexadienyl cation intermediate undergoes deprotonation to restore the aromaticity of benzene ring.

In order to form cyclohexadienyl cation intermediate, the electrophile must be reactive.

Electron donating substituents present on the benzene ring increase the reactivity towards the electrophilic aromatic substitution reactions by stabilizing the cyclohexadienyl cation intermediate.

When an electron donating substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be more stable than the cyclohexadienyl intermediate formed by benzene.

When an electron withdrawing substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be less stable than the cyclohexadienyl intermediate formed by benzene.

Stability of a cyclohexadienyl cation intermediate depends mainly on two factors – its proximity to an electron donating or electron withdrawing group and whether it is an allylic carbocation or not.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 13, Problem 55P

Interpretation Introduction

Interpretation:

The structural formula of the most stable cyclohexadienyl cation intermediate formed in each of the given reactions is to be written. Whether this carbocation is more or less stable than the cyclohexadienyl intermediate formed by benzene, is to be determined.

Concept Introduction:

Compounds containing benzene ring undergo electrophilic aromatic substitution reaction with electrophilic reagents.

The mechanism of electrophilic aromatic substitution involves two steps.

In the first step, an electrophile accepts an electron pair from pi system of benzene giving an intermediate called as cyclohexadienyl cation or arenium ion intermediate.

In the second step, the cyclohexadienyl cation intermediate undergoes deprotonation to restore the aromaticity of benzene ring.

In order to form cyclohexadienyl cation intermediate, the electrophile must be reactive.

Electron donating substituents present on the benzene ring increase the reactivity towards the electrophilic aromatic substitution reactions by stabilizing the cyclohexadienyl cation intermediate.

When an electron donating substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be more stable than the cyclohexadienyl intermediate formed by benzene.

When an electron withdrawing substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be less stable than the cyclohexadienyl intermediate formed by benzene.

Stability of a cyclohexadienyl cation intermediate depends mainly on two factors – its proximity to an electron donating or electron withdrawing group and whether it is an allylic carbocation or not.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 13, Problem 55P

Interpretation Introduction

Interpretation:

The structural formula of the most stable cyclohexadienyl cation intermediate formed in each of the given reactions is to be written. Whether this carbocation is more or less stable than the cyclohexadienyl intermediate formed by benzene, is to be determined.

Concept Introduction:

Compounds containing benzene ring undergo electrophilic aromatic substitution reaction with electrophilic reagents.

The mechanism of electrophilic aromatic substitution involves two steps.

In the first step, an electrophile accepts an electron pair from pi system of benzene giving an intermediate called as cyclohexadienyl cation or arenium ion intermediate.

In the second step, the cyclohexadienyl cation intermediate undergoes deprotonation to restore the aromaticity of benzene ring.

In order to form cyclohexadienyl cation intermediate, the electrophile must be reactive.

Electron donating substituents present on the benzene ring increase the reactivity towards the electrophilic aromatic substitution reactions by stabilizing the cyclohexadienyl cation intermediate.

When an electron donating substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be more stable than the cyclohexadienyl intermediate formed by benzene.

When an electron withdrawing substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be less stable than the cyclohexadienyl intermediate formed by benzene.

Stability of a cyclohexadienyl cation intermediate depends mainly on two factors – its proximity to an electron donating or electron withdrawing group and whether it is an allylic carbocation or not.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 13, Problem 55P

Interpretation Introduction

Interpretation:

The structural formula of the most stable cyclohexadienyl cation intermediate formed in each of the given reactions is to be written. Whether this carbocation is more or less stable than the cyclohexadienyl intermediate formed by benzene, is to be determined.

Concept Introduction:

Compounds containing benzene ring undergo electrophilic aromatic substitution reaction with electrophilic reagents.

The mechanism of electrophilic aromatic substitution involves two steps.

In the first step, an electrophile accepts an electron pair from pi system of benzene giving an intermediate called as cyclohexadienyl cation or arenium ion intermediate.

In the second step, the cyclohexadienyl cation intermediate undergoes deprotonation to restore the aromaticity of benzene ring.

In order to form cyclohexadienyl cation intermediate, the electrophile must be reactive.

Electron donating substituents present on the benzene ring increase the reactivity towards the electrophilic aromatic substitution reactions by stabilizing the cyclohexadienyl cation intermediate.

When an electron donating substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be more stable than the cyclohexadienyl intermediate formed by benzene.

When an electron withdrawing substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be less stable than the cyclohexadienyl intermediate formed by benzene.

Stability of a cyclohexadienyl cation intermediate depends mainly on two factors – its proximity to an electron donating or electron withdrawing group and whether it is an allylic carbocation or not.

Answer 6

Chapter 13, Problem 55P

Interpretation Introduction

Interpretation:

The structural formula of the most stable cyclohexadienyl cation intermediate formed in each of the given reactions is to be written. Whether this carbocation is more or less stable than the cyclohexadienyl intermediate formed by benzene, is to be determined.

Concept Introduction:

Compounds containing benzene ring undergo electrophilic aromatic substitution reaction with electrophilic reagents.

The mechanism of electrophilic aromatic substitution involves two steps.

In the first step, an electrophile accepts an electron pair from pi system of benzene giving an intermediate called as cyclohexadienyl cation or arenium ion intermediate.

In the second step, the cyclohexadienyl cation intermediate undergoes deprotonation to restore the aromaticity of benzene ring.

In order to form cyclohexadienyl cation intermediate, the electrophile must be reactive.

Electron donating substituents present on the benzene ring increase the reactivity towards the electrophilic aromatic substitution reactions by stabilizing the cyclohexadienyl cation intermediate.

When an electron donating substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be more stable than the cyclohexadienyl intermediate formed by benzene.

When an electron withdrawing substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be less stable than the cyclohexadienyl intermediate formed by benzene.

Stability of a cyclohexadienyl cation intermediate depends mainly on two factors – its proximity to an electron donating or electron withdrawing group and whether it is an allylic carbocation or not.

Answer 7

Chapter 13, Problem 55P

Interpretation Introduction

Interpretation:

The structural formula of the most stable cyclohexadienyl cation intermediate formed in each of the given reactions is to be written. Whether this carbocation is more or less stable than the cyclohexadienyl intermediate formed by benzene, is to be determined.

Concept Introduction:

Compounds containing benzene ring undergo electrophilic aromatic substitution reaction with electrophilic reagents.

The mechanism of electrophilic aromatic substitution involves two steps.

In the first step, an electrophile accepts an electron pair from pi system of benzene giving an intermediate called as cyclohexadienyl cation or arenium ion intermediate.

In the second step, the cyclohexadienyl cation intermediate undergoes deprotonation to restore the aromaticity of benzene ring.

In order to form cyclohexadienyl cation intermediate, the electrophile must be reactive.

Electron donating substituents present on the benzene ring increase the reactivity towards the electrophilic aromatic substitution reactions by stabilizing the cyclohexadienyl cation intermediate.

When an electron donating substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be more stable than the cyclohexadienyl intermediate formed by benzene.

When an electron withdrawing substituent is attached to the benzene ring, the cyclohexadienyl cation intermediate formed will be less stable than the cyclohexadienyl intermediate formed by benzene.

Stability of a cyclohexadienyl cation intermediate depends mainly on two factors – its proximity to an electron donating or electron withdrawing group and whether it is an allylic carbocation or not.

Answer 8

Expert Solution & Answer

Answer 9

Expert Solution & Answer

Answer 10

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 11

Ch. 13.2 - Based on Hammonds postulate which holds that the...Ch. 13.3 - Prob. 2P Ch. 13.3 - Using : O =N+= O : as the electrophile, write a...Ch. 13.4 - Prob. 4P Ch. 13.5 - Prob. 5P Ch. 13.6 - Prob. 6P Ch. 13.6 - Write a reasonable mechanism for the formation of...Ch. 13.6 - tert-Butylbenzene can be prepared by alkylation of...Ch. 13.6 - Prob. 9P Ch. 13.7 - The reaction shown gives a single product in 88...

Want to see the full answer?

Chapter 13 Solutions