The product formed when L-valine is treated the given set of reagents need to be predicted. Concept introduction: Esterification is a process in which a carboxylic acid reacts with an alcohol in presence of acid to form an ester by loss of water molecule. The general scheme of Fischer esterification can be shown as,

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Answer 1

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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 25, Problem 76PP

(a)

Interpretation Introduction

Interpretation:

The product formed when L-valine is treated the given set of reagents need to be predicted.

Concept introduction:

Esterification is a process in which a carboxylic acid reacts with an alcohol in presence of acid to form an ester by loss of water molecule. The general scheme of Fischer esterification can be shown as,

(b)

Interpretation Introduction

Concept introduction:

Boc-protection of amino group in amino acids is an important reaction in peptide chemistry. This prevents the amino group from involving additional reactions forming by-products. The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group. Boc-protection can be done by reaction of amino acid with di-tert-butyl dicarbonate. The steps involved in Boc-protection of amino acid are,

Nucleophilic attack to form tetrahedral intermediate

Loss of leaving group to reform carbonyl

Proton transfer to give protected amino acid

(c)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

(d)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

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Assign ALL signals for the proton and carbon NMR spectra on the following pages.

7.5 1.93 2.05 C B A 4 3 5 The Joh. 9 7 8 1 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 7 8 0.86 OH 10 4 3 5 1 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 7 8 CI 4 3 5 1 2 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 2.21 4.00 1.5 2.00 2.07 1.0 ppm 2.76

Assign the functional group bands on the IR spectra.

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 25, Problem 76PP

(a)

Interpretation Introduction

Interpretation:

The product formed when L-valine is treated the given set of reagents need to be predicted.

Concept introduction:

Esterification is a process in which a carboxylic acid reacts with an alcohol in presence of acid to form an ester by loss of water molecule. The general scheme of Fischer esterification can be shown as,

(b)

Interpretation Introduction

Concept introduction:

Boc-protection of amino group in amino acids is an important reaction in peptide chemistry. This prevents the amino group from involving additional reactions forming by-products. The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group. Boc-protection can be done by reaction of amino acid with di-tert-butyl dicarbonate. The steps involved in Boc-protection of amino acid are,

Nucleophilic attack to form tetrahedral intermediate

Loss of leaving group to reform carbonyl

Proton transfer to give protected amino acid

(c)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

(d)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

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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 25, Problem 76PP

(a)

Interpretation Introduction

Interpretation:

The product formed when L-valine is treated the given set of reagents need to be predicted.

Concept introduction:

Esterification is a process in which a carboxylic acid reacts with an alcohol in presence of acid to form an ester by loss of water molecule. The general scheme of Fischer esterification can be shown as,

(b)

Interpretation Introduction

Concept introduction:

Boc-protection of amino group in amino acids is an important reaction in peptide chemistry. This prevents the amino group from involving additional reactions forming by-products. The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group. Boc-protection can be done by reaction of amino acid with di-tert-butyl dicarbonate. The steps involved in Boc-protection of amino acid are,

Nucleophilic attack to form tetrahedral intermediate

Loss of leaving group to reform carbonyl

Proton transfer to give protected amino acid

(c)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

(d)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

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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 25, Problem 76PP

(a)

Interpretation Introduction

Interpretation:

The product formed when L-valine is treated the given set of reagents need to be predicted.

Concept introduction:

Esterification is a process in which a carboxylic acid reacts with an alcohol in presence of acid to form an ester by loss of water molecule. The general scheme of Fischer esterification can be shown as,

(b)

Interpretation Introduction

Concept introduction:

Boc-protection of amino group in amino acids is an important reaction in peptide chemistry. This prevents the amino group from involving additional reactions forming by-products. The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group. Boc-protection can be done by reaction of amino acid with di-tert-butyl dicarbonate. The steps involved in Boc-protection of amino acid are,

Nucleophilic attack to form tetrahedral intermediate

Loss of leaving group to reform carbonyl

Proton transfer to give protected amino acid

(c)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

(d)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

Expert Solution & Answer

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Answer 5

Chapter 25, Problem 76PP

(a)

Interpretation Introduction

Interpretation:

The product formed when L-valine is treated the given set of reagents need to be predicted.

Concept introduction:

Esterification is a process in which a carboxylic acid reacts with an alcohol in presence of acid to form an ester by loss of water molecule. The general scheme of Fischer esterification can be shown as,

(b)

Interpretation Introduction

Concept introduction:

Boc-protection of amino group in amino acids is an important reaction in peptide chemistry. This prevents the amino group from involving additional reactions forming by-products. The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group. Boc-protection can be done by reaction of amino acid with di-tert-butyl dicarbonate. The steps involved in Boc-protection of amino acid are,

Nucleophilic attack to form tetrahedral intermediate

Loss of leaving group to reform carbonyl

Proton transfer to give protected amino acid

(c)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

(d)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

Answer 6

Chapter 25, Problem 76PP

(a)

Interpretation Introduction

Interpretation:

The product formed when L-valine is treated the given set of reagents need to be predicted.

Concept introduction:

Esterification is a process in which a carboxylic acid reacts with an alcohol in presence of acid to form an ester by loss of water molecule. The general scheme of Fischer esterification can be shown as,

Answer 7

Chapter 25, Problem 76PP

(a)

Interpretation Introduction

Interpretation:

The product formed when L-valine is treated the given set of reagents need to be predicted.

Concept introduction:

Esterification is a process in which a carboxylic acid reacts with an alcohol in presence of acid to form an ester by loss of water molecule. The general scheme of Fischer esterification can be shown as,

Answer 8

(b)

Interpretation Introduction

Concept introduction:

Boc-protection of amino group in amino acids is an important reaction in peptide chemistry. This prevents the amino group from involving additional reactions forming by-products. The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group. Boc-protection can be done by reaction of amino acid with di-tert-butyl dicarbonate. The steps involved in Boc-protection of amino acid are,

Nucleophilic attack to form tetrahedral intermediate

Loss of leaving group to reform carbonyl

Proton transfer to give protected amino acid

Answer 9

(b)

Interpretation Introduction

Concept introduction:

Boc-protection of amino group in amino acids is an important reaction in peptide chemistry. This prevents the amino group from involving additional reactions forming by-products. The nitrogen atom of carbamate is less nucleophilic than the nitrogen atom of amine because its lone pair is delocalized by the neighboring carboxyl group. Boc-protection can be done by reaction of amino acid with di-tert-butyl dicarbonate. The steps involved in Boc-protection of amino acid are,

Nucleophilic attack to form tetrahedral intermediate

Loss of leaving group to reform carbonyl

Proton transfer to give protected amino acid

Answer 10

(c)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

Answer 11

(c)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

Answer 12

(d)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

Answer 13

(d)

Interpretation Introduction

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 25.2 - Prob. 1CC Ch. 25.2 - Prob. 2CC Ch. 25.2 - Prob. 3CC Ch. 25.2 - Prob. 1LTS Ch. 25.2 - Prob. 4PTS Ch. 25.2 - Prob. 7CC Ch. 25.2 - Prob. 8CC Ch. 25.2 - Prob. 9CC Ch. 25.2 - Prob. 10CC Ch. 25.2 - Prob. 11CC

Concept introduction: Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

Concept introduction: Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

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Chapter 25 Solutions

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.

Concept introduction:

Amino acid has both acidic and basic group, namely carboxylic acid and amine group respectively. Deprotonation or protonation can occur depending upon the conditions. The carboxylic acid is deprotonated in basic condition and amine group is protonated at acidic conditions.