(a) Interpretation: The route of synthesis of 3 - methyl -4- nitropyridine from β - picoline is to be stated. Concept introduction: The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Question

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Answer 1

Question

Chapter 26, Problem 26.17P

Interpretation Introduction

(a)

Interpretation:

The route of synthesis of 3- methyl -4- nitropyridine from β- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(b)

Interpretation:

The route of synthesis of 4- methyl -3- nitropyridine from γ- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(c)

Interpretation:

The route of synthesis of 2-(pyridin-2-yl)acetic acid from α- picoline is to be stated.

Concept introduction:

The nucleophilic substitution reactions depend upon the nucleophilicity and concentration of the nucleophile. There are two types of nucleophilic substitution reaction.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously.

Interpretation Introduction

(d)

Interpretation:

The route of synthesis of 3- aminopyridine from β- picoline is to be stated.

Concept introduction:

The rearrangement in which acyl azides (RCO−N3) undergoes a reaction to form the amines is known as Curtius rearrangement. Acyl azide is heated in benzene or toluene, inert solvent, which results in a loss of nitrogen to form isocyanate (R−N=C=O). The acid or base hydrolysis converts the isocynate products into amines.

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Answer BOTH parts of this question. (a) Briefly explain the origin of amine basicity. Using resonance structures explain why aniline is a weaker base than methylamine. (b) Draw the structure of compound X and provide a curly arrow mechanism for the reduction in Scheme 1. X 1. NaBH4 2. H₂O Scheme 1 OH

(b) Suggest a reasonable biosynthesis for the naturally occurring alkaloid coniine (isolated from hemlock), starting from octanoic acid. Coniine

(a) Which is more reactive towards Electrophilic aromatic substitution (EAS)? (b) Which of the following is a a meta-substituted compound? (c) Which is the least reactive towards Electrophilic aromatic substitution (EAS)? (d) Which is an ortho-substituted compound?

Answer 2

Question

Chapter 26, Problem 26.17P

Interpretation Introduction

(a)

Interpretation:

The route of synthesis of 3- methyl -4- nitropyridine from β- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(b)

Interpretation:

The route of synthesis of 4- methyl -3- nitropyridine from γ- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(c)

Interpretation:

The route of synthesis of 2-(pyridin-2-yl)acetic acid from α- picoline is to be stated.

Concept introduction:

The nucleophilic substitution reactions depend upon the nucleophilicity and concentration of the nucleophile. There are two types of nucleophilic substitution reaction.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously.

Interpretation Introduction

(d)

Interpretation:

The route of synthesis of 3- aminopyridine from β- picoline is to be stated.

Concept introduction:

The rearrangement in which acyl azides (RCO−N3) undergoes a reaction to form the amines is known as Curtius rearrangement. Acyl azide is heated in benzene or toluene, inert solvent, which results in a loss of nitrogen to form isocyanate (R−N=C=O). The acid or base hydrolysis converts the isocynate products into amines.

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Answer 3

Question

Chapter 26, Problem 26.17P

Interpretation Introduction

(a)

Interpretation:

The route of synthesis of 3- methyl -4- nitropyridine from β- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(b)

Interpretation:

The route of synthesis of 4- methyl -3- nitropyridine from γ- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(c)

Interpretation:

The route of synthesis of 2-(pyridin-2-yl)acetic acid from α- picoline is to be stated.

Concept introduction:

The nucleophilic substitution reactions depend upon the nucleophilicity and concentration of the nucleophile. There are two types of nucleophilic substitution reaction.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously.

Interpretation Introduction

(d)

Interpretation:

The route of synthesis of 3- aminopyridine from β- picoline is to be stated.

Concept introduction:

The rearrangement in which acyl azides (RCO−N3) undergoes a reaction to form the amines is known as Curtius rearrangement. Acyl azide is heated in benzene or toluene, inert solvent, which results in a loss of nitrogen to form isocyanate (R−N=C=O). The acid or base hydrolysis converts the isocynate products into amines.

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Answer 4

Question

Chapter 26, Problem 26.17P

Interpretation Introduction

(a)

Interpretation:

The route of synthesis of 3- methyl -4- nitropyridine from β- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(b)

Interpretation:

The route of synthesis of 4- methyl -3- nitropyridine from γ- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(c)

Interpretation:

The route of synthesis of 2-(pyridin-2-yl)acetic acid from α- picoline is to be stated.

Concept introduction:

The nucleophilic substitution reactions depend upon the nucleophilicity and concentration of the nucleophile. There are two types of nucleophilic substitution reaction.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously.

Interpretation Introduction

(d)

Interpretation:

The route of synthesis of 3- aminopyridine from β- picoline is to be stated.

Concept introduction:

The rearrangement in which acyl azides (RCO−N3) undergoes a reaction to form the amines is known as Curtius rearrangement. Acyl azide is heated in benzene or toluene, inert solvent, which results in a loss of nitrogen to form isocyanate (R−N=C=O). The acid or base hydrolysis converts the isocynate products into amines.

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Answer 5

Chapter 26, Problem 26.17P

Interpretation Introduction

(a)

Interpretation:

The route of synthesis of 3- methyl -4- nitropyridine from β- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(b)

Interpretation:

The route of synthesis of 4- methyl -3- nitropyridine from γ- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Interpretation Introduction

(c)

Interpretation:

The route of synthesis of 2-(pyridin-2-yl)acetic acid from α- picoline is to be stated.

Concept introduction:

The nucleophilic substitution reactions depend upon the nucleophilicity and concentration of the nucleophile. There are two types of nucleophilic substitution reaction.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously.

Interpretation Introduction

(d)

Interpretation:

The route of synthesis of 3- aminopyridine from β- picoline is to be stated.

Concept introduction:

The rearrangement in which acyl azides (RCO−N3) undergoes a reaction to form the amines is known as Curtius rearrangement. Acyl azide is heated in benzene or toluene, inert solvent, which results in a loss of nitrogen to form isocyanate (R−N=C=O). The acid or base hydrolysis converts the isocynate products into amines.

Answer 6

Chapter 26, Problem 26.17P

Interpretation Introduction

(a)

Interpretation:

The route of synthesis of 3- methyl -4- nitropyridine from β- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Answer 7

Chapter 26, Problem 26.17P

Interpretation Introduction

(a)

Interpretation:

The route of synthesis of 3- methyl -4- nitropyridine from β- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The route of synthesis of 4- methyl -3- nitropyridine from γ- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The route of synthesis of 4- methyl -3- nitropyridine from γ- picoline is to be stated.

Concept introduction:

The chemical reaction in which an electrophile replaces another functional group is called the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The route of synthesis of 2-(pyridin-2-yl)acetic acid from α- picoline is to be stated.

Concept introduction:

The nucleophilic substitution reactions depend upon the nucleophilicity and concentration of the nucleophile. There are two types of nucleophilic substitution reaction.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The route of synthesis of 2-(pyridin-2-yl)acetic acid from α- picoline is to be stated.

Concept introduction:

The nucleophilic substitution reactions depend upon the nucleophilicity and concentration of the nucleophile. There are two types of nucleophilic substitution reaction.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously.

Answer 12

Interpretation Introduction

(d)

Interpretation:

The route of synthesis of 3- aminopyridine from β- picoline is to be stated.

Concept introduction:

The rearrangement in which acyl azides (RCO−N3) undergoes a reaction to form the amines is known as Curtius rearrangement. Acyl azide is heated in benzene or toluene, inert solvent, which results in a loss of nitrogen to form isocyanate (R−N=C=O). The acid or base hydrolysis converts the isocynate products into amines.

Answer 13

Interpretation Introduction

(d)

Interpretation:

The route of synthesis of 3- aminopyridine from β- picoline is to be stated.

Concept introduction:

The rearrangement in which acyl azides (RCO−N3) undergoes a reaction to form the amines is known as Curtius rearrangement. Acyl azide is heated in benzene or toluene, inert solvent, which results in a loss of nitrogen to form isocyanate (R−N=C=O). The acid or base hydrolysis converts the isocynate products into amines.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 26 - Prob. 26.1P Ch. 26 - Prob. 26.2P Ch. 26 - Prob. 26.3P Ch. 26 - Prob. 26.4P Ch. 26 - Prob. 26.5P Ch. 26 - Prob. 26.6P Ch. 26 - Prob. 26.7P Ch. 26 - Prob. 26.8P Ch. 26 - Prob. 26.9P Ch. 26 - Prob. 26.10P

Solution Summary: The author explains the chemical reaction in which an electrophile replaces another functional group is known as electrophic aromatic substitution. The synthesis route for the formation of 3- methyl

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Chapter 26 Solutions