The mechanism for the given reaction has to be proposed. Concept introduction: Carboxylic acid shows nucleophilic acyl substitution reaction. The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon. The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form. The H 2 O group gets eliminated from the tetrahedral intermediate to again from the carboxylic acid.

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Answer 1

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 11, Problem 52P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction has to be proposed.

Concept introduction:

Carboxylic acid shows nucleophilic acyl substitution reaction. The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon. The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form. The H2O group gets eliminated from the tetrahedral intermediate to again from the carboxylic acid.

(b)

Interpretation Introduction

Interpretation:

To predict the reside of labeled oxygen in the product when a carboxylic acid is dissolved in isotopically labeled methanol and acid catalyst is added to it.

Concept introduction:

Carboxylic acid reacts with alcohol in the presence of a strong acid to form an ester. Carbonyl oxygen of carboxylic acid gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Alcohol can act as a nucleophile which gets attached to the carbonyl carbon after that tetrahedral intermediate is formed. A proton is removed from alkoxy group (−OR) group then the hydroxy group gets eliminated to form an ester.

(c)

Interpretation Introduction

Interpretation:

To predict the labeled reside in the product when ester is dissolved in isotopically labeled water(H2O18) and acid catalyst is added to them.

Concept introduction:

Ester undergoes hydrolysis when dissolved in water with acid. Carbonyl oxygen of ester gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Water can act as a nucleophile which gets attached to the carbonyl carbon of ester after that tetrahedral intermediate is formed. A proton is removed from −OH2 group then the alkoxy (−OR) group gets eliminated to producecarboxylic acid and water.

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Answer 2

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 11, Problem 52P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction has to be proposed.

Concept introduction:

Carboxylic acid shows nucleophilic acyl substitution reaction. The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon. The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form. The H2O group gets eliminated from the tetrahedral intermediate to again from the carboxylic acid.

(b)

Interpretation Introduction

Interpretation:

To predict the reside of labeled oxygen in the product when a carboxylic acid is dissolved in isotopically labeled methanol and acid catalyst is added to it.

Concept introduction:

Carboxylic acid reacts with alcohol in the presence of a strong acid to form an ester. Carbonyl oxygen of carboxylic acid gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Alcohol can act as a nucleophile which gets attached to the carbonyl carbon after that tetrahedral intermediate is formed. A proton is removed from alkoxy group (−OR) group then the hydroxy group gets eliminated to form an ester.

(c)

Interpretation Introduction

Interpretation:

To predict the labeled reside in the product when ester is dissolved in isotopically labeled water(H2O18) and acid catalyst is added to them.

Concept introduction:

Ester undergoes hydrolysis when dissolved in water with acid. Carbonyl oxygen of ester gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Water can act as a nucleophile which gets attached to the carbonyl carbon of ester after that tetrahedral intermediate is formed. A proton is removed from −OH2 group then the alkoxy (−OR) group gets eliminated to producecarboxylic acid and water.

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Answer 3

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 11, Problem 52P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction has to be proposed.

Concept introduction:

Carboxylic acid shows nucleophilic acyl substitution reaction. The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon. The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form. The H2O group gets eliminated from the tetrahedral intermediate to again from the carboxylic acid.

(b)

Interpretation Introduction

Interpretation:

To predict the reside of labeled oxygen in the product when a carboxylic acid is dissolved in isotopically labeled methanol and acid catalyst is added to it.

Concept introduction:

Carboxylic acid reacts with alcohol in the presence of a strong acid to form an ester. Carbonyl oxygen of carboxylic acid gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Alcohol can act as a nucleophile which gets attached to the carbonyl carbon after that tetrahedral intermediate is formed. A proton is removed from alkoxy group (−OR) group then the hydroxy group gets eliminated to form an ester.

(c)

Interpretation Introduction

Interpretation:

To predict the labeled reside in the product when ester is dissolved in isotopically labeled water(H2O18) and acid catalyst is added to them.

Concept introduction:

Ester undergoes hydrolysis when dissolved in water with acid. Carbonyl oxygen of ester gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Water can act as a nucleophile which gets attached to the carbonyl carbon of ester after that tetrahedral intermediate is formed. A proton is removed from −OH2 group then the alkoxy (−OR) group gets eliminated to producecarboxylic acid and water.

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Answer 4

Question

Definition Definition Class of organic compounds that contain a carboxyl group ( - COOH ) and has a general formula R - COOH or R - CO 2 H , where R refers to the alkyl, alkenyl, aryl, or other groups. They can undergo different chemical reactions, such as acid-base reactions, esterification, and oxidation. These are essential components of living organisms, playing important roles in metabolic processes, signaling, and as pharmaceuticals.

Chapter 11, Problem 52P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction has to be proposed.

Concept introduction:

Carboxylic acid shows nucleophilic acyl substitution reaction. The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon. The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form. The H2O group gets eliminated from the tetrahedral intermediate to again from the carboxylic acid.

(b)

Interpretation Introduction

Interpretation:

To predict the reside of labeled oxygen in the product when a carboxylic acid is dissolved in isotopically labeled methanol and acid catalyst is added to it.

Concept introduction:

Carboxylic acid reacts with alcohol in the presence of a strong acid to form an ester. Carbonyl oxygen of carboxylic acid gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Alcohol can act as a nucleophile which gets attached to the carbonyl carbon after that tetrahedral intermediate is formed. A proton is removed from alkoxy group (−OR) group then the hydroxy group gets eliminated to form an ester.

(c)

Interpretation Introduction

Interpretation:

To predict the labeled reside in the product when ester is dissolved in isotopically labeled water(H2O18) and acid catalyst is added to them.

Concept introduction:

Ester undergoes hydrolysis when dissolved in water with acid. Carbonyl oxygen of ester gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Water can act as a nucleophile which gets attached to the carbonyl carbon of ester after that tetrahedral intermediate is formed. A proton is removed from −OH2 group then the alkoxy (−OR) group gets eliminated to producecarboxylic acid and water.

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Answer 5

Chapter 11, Problem 52P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction has to be proposed.

Concept introduction:

Carboxylic acid shows nucleophilic acyl substitution reaction. The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon. The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form. The H2O group gets eliminated from the tetrahedral intermediate to again from the carboxylic acid.

(b)

Interpretation Introduction

Interpretation:

To predict the reside of labeled oxygen in the product when a carboxylic acid is dissolved in isotopically labeled methanol and acid catalyst is added to it.

Concept introduction:

Carboxylic acid reacts with alcohol in the presence of a strong acid to form an ester. Carbonyl oxygen of carboxylic acid gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Alcohol can act as a nucleophile which gets attached to the carbonyl carbon after that tetrahedral intermediate is formed. A proton is removed from alkoxy group (−OR) group then the hydroxy group gets eliminated to form an ester.

(c)

Interpretation Introduction

Interpretation:

To predict the labeled reside in the product when ester is dissolved in isotopically labeled water(H2O18) and acid catalyst is added to them.

Concept introduction:

Ester undergoes hydrolysis when dissolved in water with acid. Carbonyl oxygen of ester gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Water can act as a nucleophile which gets attached to the carbonyl carbon of ester after that tetrahedral intermediate is formed. A proton is removed from −OH2 group then the alkoxy (−OR) group gets eliminated to producecarboxylic acid and water.

Answer 6

Chapter 11, Problem 52P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction has to be proposed.

Concept introduction:

Carboxylic acid shows nucleophilic acyl substitution reaction. The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon. The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form. The H2O group gets eliminated from the tetrahedral intermediate to again from the carboxylic acid.

Answer 7

Chapter 11, Problem 52P

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction has to be proposed.

Concept introduction:

Carboxylic acid shows nucleophilic acyl substitution reaction. The acid protonates the oxygen of carboxylic acid which results in increased electrophilicity of the carbonyl carbon. The water molecule acts as a nucleophile and gets attached to the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate is formed stays in equilibrium with protonated and unprotonated form. The H2O group gets eliminated from the tetrahedral intermediate to again from the carboxylic acid.

Answer 8

(b)

Interpretation Introduction

Interpretation:

To predict the reside of labeled oxygen in the product when a carboxylic acid is dissolved in isotopically labeled methanol and acid catalyst is added to it.

Concept introduction:

Carboxylic acid reacts with alcohol in the presence of a strong acid to form an ester. Carbonyl oxygen of carboxylic acid gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Alcohol can act as a nucleophile which gets attached to the carbonyl carbon after that tetrahedral intermediate is formed. A proton is removed from alkoxy group (−OR) group then the hydroxy group gets eliminated to form an ester.

Answer 9

(b)

Interpretation Introduction

Interpretation:

To predict the reside of labeled oxygen in the product when a carboxylic acid is dissolved in isotopically labeled methanol and acid catalyst is added to it.

Concept introduction:

Carboxylic acid reacts with alcohol in the presence of a strong acid to form an ester. Carbonyl oxygen of carboxylic acid gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Alcohol can act as a nucleophile which gets attached to the carbonyl carbon after that tetrahedral intermediate is formed. A proton is removed from alkoxy group (−OR) group then the hydroxy group gets eliminated to form an ester.

Answer 10

(c)

Interpretation Introduction

Interpretation:

To predict the labeled reside in the product when ester is dissolved in isotopically labeled water(H2O18) and acid catalyst is added to them.

Concept introduction:

Ester undergoes hydrolysis when dissolved in water with acid. Carbonyl oxygen of ester gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Water can act as a nucleophile which gets attached to the carbonyl carbon of ester after that tetrahedral intermediate is formed. A proton is removed from −OH2 group then the alkoxy (−OR) group gets eliminated to producecarboxylic acid and water.

Answer 11

(c)

Interpretation Introduction

Interpretation:

To predict the labeled reside in the product when ester is dissolved in isotopically labeled water(H2O18) and acid catalyst is added to them.

Concept introduction:

Ester undergoes hydrolysis when dissolved in water with acid. Carbonyl oxygen of ester gets protonated by the acid resulting in increased electrophilicity of the carbonyl carbon. Water can act as a nucleophile which gets attached to the carbonyl carbon of ester after that tetrahedral intermediate is formed. A proton is removed from −OH2 group then the alkoxy (−OR) group gets eliminated to producecarboxylic acid and water.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 11.1 - The aromas of many flowers and fruits are due to...Ch. 11.1 - Name the following compounds:Ch. 11.1 - Prob. 3P Ch. 11.2 - Prob. 4P Ch. 11.2 - Prob. 5P Ch. 11.4 - a. What is the product of the reaction of acetyl...Ch. 11.4 - Prob. 7P Ch. 11.5 - Using the pKa values listed in Table 11.1, predict...Ch. 11.6 - Starting with acetyl chloride, what neutral...Ch. 11.6 - Prob. 10P

Solution Summary: The author explains the nucleophilic acyl substitution reaction of carboxylic acid, which results in increased electrophilicity of the carbonyl carbon. The tetrahedral intermediate stays in equilibrium with proto

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Chapter 11 Solutions