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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.

Pyridine undergoes electrophilic aromatic substitution preferentially at the 3 position as illustrated by the synthesis of 3-nitropyridine. NO2 H,SO, + HNO3 + H2O 300°C Pyridine 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 NO,+ at the 2, 3, and 4 positions of the conjugate acid of pyridine. From examination of these intermediates, offer an explanation for preferential nitration at the 3 position.

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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), 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.