Reason for the preferential of nitration of pyridine at 3 rd position has to be given and also resonance contributors for the intermediate formed by attack of NO 2 + at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

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Answer 1

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Chapter 22, Problem 22.8P

Interpretation Introduction

Interpretation:

Reason for the preferential of nitration of pyridine at 3^rd position has to be given and also resonance contributors for the intermediate formed by attack of NO2+ at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

Expert Solution & Answer

Explanation of Solution

Pyridine is a base, so in the presence of acid it will be protonated. For nitration at the 3^rd position, the additional positive charge is delocalized on three carbon atoms of the pyridine ring. In this case, none of the resonance structures has a +2 charge on the same atom.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 1

For nitration at the 2^nd position or 4^th position, the additional positive charge on the cation intermediate is also delocalized on three atoms of the pyridine ring, but one of the resonance structure has a +2 charge on nitrogen atom. This situation is less stable than that happens for nitration at the 3^rd position.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 2

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Pyridine undergoes electrophilic aromatic substitution preferentially at the 3 position as illustrated by the synthesis of 3-nitropyridine. Under these acidic conditions, the species undergoing nitration is not pyridine, but its conjugate acid. Write resonance contributing structures for the intermediate formed by attack of NO2+ at the 2, 3, and 4 positions of the conjugate add of pyridine. From examination of these intermediates, offer an explanation for preferential nitration at the 3 position.

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Rank the following carboxylic acids derivatives based on their reactivity towards nucleophiles (1-most reactive - 4- least reactive), and describe the structural features you use to detrmine your ranking.

Answer 2

Question

Chapter 22, Problem 22.8P

Interpretation Introduction

Interpretation:

Reason for the preferential of nitration of pyridine at 3^rd position has to be given and also resonance contributors for the intermediate formed by attack of NO2+ at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

Expert Solution & Answer

Explanation of Solution

Pyridine is a base, so in the presence of acid it will be protonated. For nitration at the 3^rd position, the additional positive charge is delocalized on three carbon atoms of the pyridine ring. In this case, none of the resonance structures has a +2 charge on the same atom.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 1

For nitration at the 2^nd position or 4^th position, the additional positive charge on the cation intermediate is also delocalized on three atoms of the pyridine ring, but one of the resonance structure has a +2 charge on nitrogen atom. This situation is less stable than that happens for nitration at the 3^rd position.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 2

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Answer 3

Question

Chapter 22, Problem 22.8P

Interpretation Introduction

Interpretation:

Reason for the preferential of nitration of pyridine at 3^rd position has to be given and also resonance contributors for the intermediate formed by attack of NO2+ at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

Expert Solution & Answer

Explanation of Solution

Pyridine is a base, so in the presence of acid it will be protonated. For nitration at the 3^rd position, the additional positive charge is delocalized on three carbon atoms of the pyridine ring. In this case, none of the resonance structures has a +2 charge on the same atom.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 1

For nitration at the 2^nd position or 4^th position, the additional positive charge on the cation intermediate is also delocalized on three atoms of the pyridine ring, but one of the resonance structure has a +2 charge on nitrogen atom. This situation is less stable than that happens for nitration at the 3^rd position.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 2

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Answer 4

Question

Chapter 22, Problem 22.8P

Interpretation Introduction

Interpretation:

Reason for the preferential of nitration of pyridine at 3^rd position has to be given and also resonance contributors for the intermediate formed by attack of NO2+ at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

Expert Solution & Answer

Explanation of Solution

Pyridine is a base, so in the presence of acid it will be protonated. For nitration at the 3^rd position, the additional positive charge is delocalized on three carbon atoms of the pyridine ring. In this case, none of the resonance structures has a +2 charge on the same atom.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 1

For nitration at the 2^nd position or 4^th position, the additional positive charge on the cation intermediate is also delocalized on three atoms of the pyridine ring, but one of the resonance structure has a +2 charge on nitrogen atom. This situation is less stable than that happens for nitration at the 3^rd position.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 2

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Answer 5

Chapter 22, Problem 22.8P

Interpretation Introduction

Interpretation:

Reason for the preferential of nitration of pyridine at 3^rd position has to be given and also resonance contributors for the intermediate formed by attack of NO2+ at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

Expert Solution & Answer

Explanation of Solution

Pyridine is a base, so in the presence of acid it will be protonated. For nitration at the 3^rd position, the additional positive charge is delocalized on three carbon atoms of the pyridine ring. In this case, none of the resonance structures has a +2 charge on the same atom.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 1

For nitration at the 2^nd position or 4^th position, the additional positive charge on the cation intermediate is also delocalized on three atoms of the pyridine ring, but one of the resonance structure has a +2 charge on nitrogen atom. This situation is less stable than that happens for nitration at the 3^rd position.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 2

Answer 6

Chapter 22, Problem 22.8P

Interpretation Introduction

Interpretation:

Reason for the preferential of nitration of pyridine at 3^rd position has to be given and also resonance contributors for the intermediate formed by attack of NO2+ at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

Expert Solution & Answer

Explanation of Solution

Pyridine is a base, so in the presence of acid it will be protonated. For nitration at the 3^rd position, the additional positive charge is delocalized on three carbon atoms of the pyridine ring. In this case, none of the resonance structures has a +2 charge on the same atom.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 1

For nitration at the 2^nd position or 4^th position, the additional positive charge on the cation intermediate is also delocalized on three atoms of the pyridine ring, but one of the resonance structure has a +2 charge on nitrogen atom. This situation is less stable than that happens for nitration at the 3^rd position.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 2

Answer 7

Chapter 22, Problem 22.8P

Interpretation Introduction

Interpretation:

Reason for the preferential of nitration of pyridine at 3^rd position has to be given and also resonance contributors for the intermediate formed by attack of NO2+ at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

Answer 8

Expert Solution & Answer

Explanation of Solution

Pyridine is a base, so in the presence of acid it will be protonated. For nitration at the 3^rd position, the additional positive charge is delocalized on three carbon atoms of the pyridine ring. In this case, none of the resonance structures has a +2 charge on the same atom.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 1

For nitration at the 2^nd position or 4^th position, the additional positive charge on the cation intermediate is also delocalized on three atoms of the pyridine ring, but one of the resonance structure has a +2 charge on nitrogen atom. This situation is less stable than that happens for nitration at the 3^rd position.

Organic Chemistry, Chapter 22, Problem 22.8P , additional homework tip 2

Answer 9

Expert Solution & Answer

Answer 10

Expert Solution & Answer

Answer 11

Ch. 22.1 - Prob. 22.1P Ch. 22.1 - Write a structural formula for the product from...Ch. 22.1 - Prob. 22.3P Ch. 22.2 - Prob. 22.4P Ch. 22.2 - Predict the major produce(s) of each electrophilic...Ch. 22.3 - In SN2 reactions of haloalkanes, the order of...Ch. 22 - Prob. 22.8P Ch. 22 - Prob. 22.9P Ch. 22 - Addition of m-xylene to the strongly acidic...Ch. 22 - Addition of tert-butylbenzene to the strongly...

Reason for the preferential of nitration of pyridine at 3 rd position has to be given and also resonance contributors for the intermediate formed by attack of NO 2 + at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

Interpretation: Reason for the preferential of nitration of pyridine at 3rd position has to be given and also resonance contributors for the intermediate formed by attack of NO2+ at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.

Explanation of Solution

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Chapter 22 Solutions

Interpretation:

Reason for the preferential of nitration of pyridine at 3^rd position has to be given and also resonance contributors for the intermediate formed by attack of NO2+ at the 2, 3, 4 positions of the conjugate acid of pyridine has to be given.