To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide. Concept introduction: Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present. Symmetrical ketone=Symmetrical α position =one enolate ion Unsymmetrical Ketone=Unymmetrical α position = two enolate ion To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

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Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21.1, Problem 6CC

(a)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(b)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(c)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(d)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21.1, Problem 6CC

(a)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(b)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(c)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(d)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21.1, Problem 6CC

(a)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(b)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(c)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(d)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 21.1, Problem 6CC

(a)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(b)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(c)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(d)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 5

Chapter 21.1, Problem 6CC

(a)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(b)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(c)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

(d)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Answer 6

Chapter 21.1, Problem 6CC

(a)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Answer 7

Chapter 21.1, Problem 6CC

(a)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Answer 8

(b)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Answer 9

(b)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Answer 10

(c)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Answer 11

(c)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Answer 12

(d)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Answer 13

(d)

Interpretation Introduction

Interpretation:

To draw all resonance structures of enolate ion formed from the given set of compounds and predict whether a substantial amount of starting ketone will be present with enolate after equilibrium when treated with sodium ethoxide.

Concept introduction:

Keto-enol isomerization is possible when a keto group present in the compound has a movable hydrogen atom in the next carbon attached to the carbonyl group. This occurs generally in almost all keto compounds where a chemical equilibria is present between the keto and enol form of the compound. Conversion of keto to its enol form is known as keto-enol tautomerisation. This conversion occurs in presence of acid or base. The ion fomed after the deprotonation using base at the α position leads to enolate ion. If the negative charge is delocalized in the resonance structures means a substantial amount of starting ketone will be present.

Symmetrical ketone=Symmetrical α position =one enolate ion

Unsymmetrical Ketone=Unymmetrical α position = two enolate ion

To Draw : The resonance structure of enolate ion and predict whether substantial amount of starting ketone will be present after equilibrium if sodium ethoxide is used as base.

Answer 14

Expert Solution & Answer

Answer 15

Expert Solution & Answer

Answer 16

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Answer 17

Ch. 21.1 - Prob. 1CC Ch. 21.1 - Prob. 2CC Ch. 21.1 - Prob. 3CC Ch. 21.1 - Prob. 1LTS Ch. 21.1 - Prob. 4PTS Ch. 21.1 - Prob. 5ATS Ch. 21.1 - Prob. 6CC Ch. 21.1 - Prob. 7CC Ch. 21.2 - Prob. 8CC Ch. 21.2 - Prob. 9CC

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Chapter 21 Solutions