Structure of the products obtained need to be drawn for the given set of reactions. Concept introduction: Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol. Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone .

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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 22, Problem 86PP

(a)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol. Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

(b)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

Deprotonation of α carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone
(nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

If the starting material has two ester group then intramolecular claisen condensation takes place to form a cyclic structure.

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol.

Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

To Draw : To draw the structure of product for the given transformation

(c)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

When a keto compound is treated with bromine in presence of acid installs α position. The formed brominated compound in presence of pyridine undergoes elimination to form an α,β unsaturated ketone. Treatment of α,β unsaturated ketone with lithium dialkyl cuprate installs alkyl group at the β position via Michael addition. This when treated with methyl iodide installs a methyl group at α position.

(d)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

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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 22, Problem 86PP

(a)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol. Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

(b)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

Deprotonation of α carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone
(nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

If the starting material has two ester group then intramolecular claisen condensation takes place to form a cyclic structure.

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol.

Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

To Draw : To draw the structure of product for the given transformation

(c)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

When a keto compound is treated with bromine in presence of acid installs α position. The formed brominated compound in presence of pyridine undergoes elimination to form an α,β unsaturated ketone. Treatment of α,β unsaturated ketone with lithium dialkyl cuprate installs alkyl group at the β position via Michael addition. This when treated with methyl iodide installs a methyl group at α position.

(d)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

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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 22, Problem 86PP

(a)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol. Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

(b)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

Deprotonation of α carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone
(nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

If the starting material has two ester group then intramolecular claisen condensation takes place to form a cyclic structure.

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol.

Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

To Draw : To draw the structure of product for the given transformation

(c)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

When a keto compound is treated with bromine in presence of acid installs α position. The formed brominated compound in presence of pyridine undergoes elimination to form an α,β unsaturated ketone. Treatment of α,β unsaturated ketone with lithium dialkyl cuprate installs alkyl group at the β position via Michael addition. This when treated with methyl iodide installs a methyl group at α position.

(d)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

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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 22, Problem 86PP

(a)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol. Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

(b)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

Deprotonation of α carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone
(nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

If the starting material has two ester group then intramolecular claisen condensation takes place to form a cyclic structure.

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol.

Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

To Draw : To draw the structure of product for the given transformation

(c)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

When a keto compound is treated with bromine in presence of acid installs α position. The formed brominated compound in presence of pyridine undergoes elimination to form an α,β unsaturated ketone. Treatment of α,β unsaturated ketone with lithium dialkyl cuprate installs alkyl group at the β position via Michael addition. This when treated with methyl iodide installs a methyl group at α position.

(d)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

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Answer 5

Chapter 22, Problem 86PP

(a)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol. Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

(b)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

Deprotonation of α carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone
(nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

If the starting material has two ester group then intramolecular claisen condensation takes place to form a cyclic structure.

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol.

Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

To Draw : To draw the structure of product for the given transformation

(c)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

When a keto compound is treated with bromine in presence of acid installs α position. The formed brominated compound in presence of pyridine undergoes elimination to form an α,β unsaturated ketone. Treatment of α,β unsaturated ketone with lithium dialkyl cuprate installs alkyl group at the β position via Michael addition. This when treated with methyl iodide installs a methyl group at α position.

(d)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

Answer 6

Chapter 22, Problem 86PP

(a)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol. Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

Answer 7

Chapter 22, Problem 86PP

(a)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol. Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

Answer 8

(b)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

Deprotonation of α carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone
(nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

If the starting material has two ester group then intramolecular claisen condensation takes place to form a cyclic structure.

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol.

Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

To Draw : To draw the structure of product for the given transformation

Answer 9

(b)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Claisen condensation is a process where a carbon-carbon bond is formed when reaction occurs between two esters or one ester and carbonyl compound in presence of a strong base to form a β -keto ester or a β -diketone, respectively

Deprotonation of α carbon to form ester enolate

Attach of enolate ion with the carbonyl of ester or ketone
(nucleophilic attack)

Loss of alkoxide ion to reform carbonyl

If the starting material has two ester group then intramolecular claisen condensation takes place to form a cyclic structure.

Ester when treated with aqueous acid undergoes hydrolysis to form carboxylic acid and an alcohol.

Carboxylic acid having a carbonyl group in the β position undergoes decarboxylation to give a ketone.

To Draw : To draw the structure of product for the given transformation

Answer 10

(c)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

When a keto compound is treated with bromine in presence of acid installs α position. The formed brominated compound in presence of pyridine undergoes elimination to form an α,β unsaturated ketone. Treatment of α,β unsaturated ketone with lithium dialkyl cuprate installs alkyl group at the β position via Michael addition. This when treated with methyl iodide installs a methyl group at α position.

Answer 11

(c)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

When a keto compound is treated with bromine in presence of acid installs α position. The formed brominated compound in presence of pyridine undergoes elimination to form an α,β unsaturated ketone. Treatment of α,β unsaturated ketone with lithium dialkyl cuprate installs alkyl group at the β position via Michael addition. This when treated with methyl iodide installs a methyl group at α position.

Answer 12

(d)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

Answer 13

(d)

Interpretation Introduction

Interpretation:

Structure of the products obtained need to be drawn for the given set of reactions.

Concept introduction:

Carbonyl compound when treated with LDA undergoes deprotonation at the α carbon to form enolate. The enolate formed is resonance stabilized as the negative charge will be spread over other atoms too. The resonance stabilized intermediate undergoes reaction with other molecule of carbonyl (same or different) to form the respective products. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance.

Deprotonation of α carbon to form enolate

Nucleophilic attack of enolate

Answer 14

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Answer 15

Expert Solution & Answer

Answer 16

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Answer 17

Ch. 22.1 - Prob. 1CC Ch. 22.1 - Prob. 2CC Ch. 22.1 - Prob. 3CC Ch. 22.1 - Prob. 1LTS Ch. 22.1 - Prob. 4PTS Ch. 22.1 - Prob. 5ATS Ch. 22.1 - Prob. 6CC Ch. 22.1 - Prob. 7CC Ch. 22.1 - Prob. 8CC Ch. 22.2 - Prob. 9CC

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Chapter 22 Solutions