The structures of cyclohexa-2, 4-dien-1-one and its enol form are to be written, and the special factors that account for the stability of the enol form are to be identified. Concept introduction: Tautomerization is defined as the interconversion of the keto and enol forms. The keto and enol forms are tautomers. The conjugate base of both the keto and the enol forms is enolate. If the enolate accepts a proton from carbon, the keto form is formed, and if the enolate accepts a proton from oxygen, the enol form is formed.

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Answer 1

Question

Chapter 18, Problem 1PP

Interpretation Introduction

Interpretation: The structures of cyclohexa-2, 4-dien-1-one and its enol form are to be written, and the special factors that account for the stability of the enol form are to be identified.

Concept introduction:

Tautomerization is defined as the interconversion of the keto and enol forms. The keto and enol forms are tautomers.

The conjugate base of both the keto and the enol forms is enolate.

If the enolate accepts a proton from carbon, the keto form is formed, and if the enolate accepts a proton from oxygen, the enol form is formed.

Expert Solution & Answer

Answer to Problem 1PP

Solution:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 1

Due to aromaticity.

Explanation of Solution

Under acidic condition, cyclohexa-2, 4-dien-1-one converts to phenol through tautomerism. The structures of cyclohexa-2, 4-dien-1-one and its enol form are as follows:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 2

Ketones are usually more stable than enols. However, in this case, the enol form is more stable because the enol form is phenol, which is aromatic in nature, whereas, in the keto form, there is no aromatic character. Hence, due to its aromaticity, the enol form is more stable.

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Consider a solution of 0.00304 moles of 4-nitrobenzoic acid (pKa = 3.442) dissolved in 25 mL water and titrated with 0.0991 M NaOH. Calculate the pH at the equivalence point

Answer 2

Question

Chapter 18, Problem 1PP

Interpretation Introduction

Interpretation: The structures of cyclohexa-2, 4-dien-1-one and its enol form are to be written, and the special factors that account for the stability of the enol form are to be identified.

Concept introduction:

Tautomerization is defined as the interconversion of the keto and enol forms. The keto and enol forms are tautomers.

The conjugate base of both the keto and the enol forms is enolate.

If the enolate accepts a proton from carbon, the keto form is formed, and if the enolate accepts a proton from oxygen, the enol form is formed.

Expert Solution & Answer

Answer to Problem 1PP

Solution:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 1

Due to aromaticity.

Explanation of Solution

Under acidic condition, cyclohexa-2, 4-dien-1-one converts to phenol through tautomerism. The structures of cyclohexa-2, 4-dien-1-one and its enol form are as follows:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 2

Ketones are usually more stable than enols. However, in this case, the enol form is more stable because the enol form is phenol, which is aromatic in nature, whereas, in the keto form, there is no aromatic character. Hence, due to its aromaticity, the enol form is more stable.

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Answer 3

Question

Chapter 18, Problem 1PP

Interpretation Introduction

Interpretation: The structures of cyclohexa-2, 4-dien-1-one and its enol form are to be written, and the special factors that account for the stability of the enol form are to be identified.

Concept introduction:

Tautomerization is defined as the interconversion of the keto and enol forms. The keto and enol forms are tautomers.

The conjugate base of both the keto and the enol forms is enolate.

If the enolate accepts a proton from carbon, the keto form is formed, and if the enolate accepts a proton from oxygen, the enol form is formed.

Expert Solution & Answer

Answer to Problem 1PP

Solution:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 1

Due to aromaticity.

Explanation of Solution

Under acidic condition, cyclohexa-2, 4-dien-1-one converts to phenol through tautomerism. The structures of cyclohexa-2, 4-dien-1-one and its enol form are as follows:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 2

Ketones are usually more stable than enols. However, in this case, the enol form is more stable because the enol form is phenol, which is aromatic in nature, whereas, in the keto form, there is no aromatic character. Hence, due to its aromaticity, the enol form is more stable.

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Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 4

Question

Chapter 18, Problem 1PP

Interpretation Introduction

Interpretation: The structures of cyclohexa-2, 4-dien-1-one and its enol form are to be written, and the special factors that account for the stability of the enol form are to be identified.

Concept introduction:

Tautomerization is defined as the interconversion of the keto and enol forms. The keto and enol forms are tautomers.

The conjugate base of both the keto and the enol forms is enolate.

If the enolate accepts a proton from carbon, the keto form is formed, and if the enolate accepts a proton from oxygen, the enol form is formed.

Expert Solution & Answer

Answer to Problem 1PP

Solution:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 1

Due to aromaticity.

Explanation of Solution

Under acidic condition, cyclohexa-2, 4-dien-1-one converts to phenol through tautomerism. The structures of cyclohexa-2, 4-dien-1-one and its enol form are as follows:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 2

Ketones are usually more stable than enols. However, in this case, the enol form is more stable because the enol form is phenol, which is aromatic in nature, whereas, in the keto form, there is no aromatic character. Hence, due to its aromaticity, the enol form is more stable.

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Answer 5

Chapter 18, Problem 1PP

Interpretation Introduction

Interpretation: The structures of cyclohexa-2, 4-dien-1-one and its enol form are to be written, and the special factors that account for the stability of the enol form are to be identified.

Concept introduction:

Tautomerization is defined as the interconversion of the keto and enol forms. The keto and enol forms are tautomers.

The conjugate base of both the keto and the enol forms is enolate.

If the enolate accepts a proton from carbon, the keto form is formed, and if the enolate accepts a proton from oxygen, the enol form is formed.

Expert Solution & Answer

Answer to Problem 1PP

Solution:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 1

Due to aromaticity.

Explanation of Solution

Under acidic condition, cyclohexa-2, 4-dien-1-one converts to phenol through tautomerism. The structures of cyclohexa-2, 4-dien-1-one and its enol form are as follows:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 2

Ketones are usually more stable than enols. However, in this case, the enol form is more stable because the enol form is phenol, which is aromatic in nature, whereas, in the keto form, there is no aromatic character. Hence, due to its aromaticity, the enol form is more stable.

Answer 6

Chapter 18, Problem 1PP

Interpretation Introduction

Interpretation: The structures of cyclohexa-2, 4-dien-1-one and its enol form are to be written, and the special factors that account for the stability of the enol form are to be identified.

Concept introduction:

Tautomerization is defined as the interconversion of the keto and enol forms. The keto and enol forms are tautomers.

The conjugate base of both the keto and the enol forms is enolate.

If the enolate accepts a proton from carbon, the keto form is formed, and if the enolate accepts a proton from oxygen, the enol form is formed.

Expert Solution & Answer

Answer to Problem 1PP

Solution:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 1

Due to aromaticity.

Explanation of Solution

Under acidic condition, cyclohexa-2, 4-dien-1-one converts to phenol through tautomerism. The structures of cyclohexa-2, 4-dien-1-one and its enol form are as follows:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 2

Ketones are usually more stable than enols. However, in this case, the enol form is more stable because the enol form is phenol, which is aromatic in nature, whereas, in the keto form, there is no aromatic character. Hence, due to its aromaticity, the enol form is more stable.

Answer 7

Chapter 18, Problem 1PP

Interpretation Introduction

Interpretation: The structures of cyclohexa-2, 4-dien-1-one and its enol form are to be written, and the special factors that account for the stability of the enol form are to be identified.

Concept introduction:

Tautomerization is defined as the interconversion of the keto and enol forms. The keto and enol forms are tautomers.

The conjugate base of both the keto and the enol forms is enolate.

If the enolate accepts a proton from carbon, the keto form is formed, and if the enolate accepts a proton from oxygen, the enol form is formed.

Answer 8

Expert Solution & Answer

Answer to Problem 1PP

Solution:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 1

Due to aromaticity.

Answer 9

Expert Solution & Answer

Answer 10

Expert Solution & Answer

Answer 11

Explanation of Solution

Under acidic condition, cyclohexa-2, 4-dien-1-one converts to phenol through tautomerism. The structures of cyclohexa-2, 4-dien-1-one and its enol form are as follows:

Organic Chemistry, Chapter 18, Problem 1PP , additional homework tip 2

Ketones are usually more stable than enols. However, in this case, the enol form is more stable because the enol form is phenol, which is aromatic in nature, whereas, in the keto form, there is no aromatic character. Hence, due to its aromaticity, the enol form is more stable.

Answer 12

Ch. 18 - Prob. 1PP Ch. 18 - Practice Problem 18.2 Would optically active...Ch. 18 - Prob. 3PP Ch. 18 - Practice Problem 18.4 Why do we say that the...Ch. 18 - Prob. 5PP Ch. 18 - Practice Problem 18.6 (a) Write a reaction...Ch. 18 - PRACTICE PROBLEM 18.7 Show how you would use the...Ch. 18 - Practice Problem 18.8 The acetoacetic ester...Ch. 18 - Practice Problem 18.9 In the synthesis of the keto...Ch. 18 - PRACTICE PROBLEM 18.10 How would you use the...

Concept explainers

Answer to Problem 1PP

Explanation of Solution

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Chapter 18 Solutions