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.

Question

Want to see more full solutions like this?

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.

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

(c) The following data have been obtained for the hydrolysis of sucrose, C12H22O11, to glucose, C6H12O6, and fructose C6H12O6, in acidic solution: C12H22O11 + H2O → C6H12O6 + C6H12O6 [sucrose]/mol dm³ t/min 0 0.316 14 0.300 39 0.274 60 0.256 80 0.238 110 0.211 (i) Graphically prove the order of the reaction and determine the rate constant of the reaction. (ii) Determine the half-life, t½ for the hydrolysis of sucrose.

(III) adsorbent (b) Adsorption of the hexacyanoferrate (III) ion, [Fe(CN)6] ³, on y-Al2O3 from aqueous solution was examined. The adsorption was modelled using a modified Langmuir isotherm, yielding the following values of Kat pH = 6.5: (ii) T/K 10-10 K 280 2.505 295 1.819 310 1.364 325 1.050 Determine the enthalpy of adsorption, AadsHⓇ. If the reported value of entropy of adsorption, Aads Se = 146 J K-1 mol-1 under the above conditions, determine Aads Gº.

with full details solution please

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.

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 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.

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 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.

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 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

Want to see more full solutions like this?

Chapter 18 Solutions