(a) Interpretation: The curved-arrow mechanism for the given reaction is to be stated. The role of weak acid ammonium chloride is also to be stated. Concept introduction: The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

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Answer 1

Question

Chapter 11, Problem 11.70AP

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the given reaction is to be stated. The role of weak acid ammonium chloride is also to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the reaction of aziridine requires a weak acid is to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

The suggestion of using a dilute solution of strong acid HCl as an even better catalyst for given reaction is to be criticized.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

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Students have asked these similar questions

(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enal

Give reasons: (i) Bond length of C = O in carboxylic acids is slightly larger than C = O bond length in carbonyl compounds. (ii) There are two –NH2 groups in semicarbazide. However, only one –NH2 group is involved in the formation of semicarbazones. (iii) Benzoic acid is less soluble in water than acetic acid. (iv) Formic acid is a stronger acid than acetic acid.

Aniline (conjugate acid pKa 4.63) is a considerably stronger base than diphenylamine (pKa 0.79). Account for these marked differences.

Answer 2

Question

Chapter 11, Problem 11.70AP

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the given reaction is to be stated. The role of weak acid ammonium chloride is also to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the reaction of aziridine requires a weak acid is to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

The suggestion of using a dilute solution of strong acid HCl as an even better catalyst for given reaction is to be criticized.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

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Answer 3

Question

Chapter 11, Problem 11.70AP

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the given reaction is to be stated. The role of weak acid ammonium chloride is also to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the reaction of aziridine requires a weak acid is to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

The suggestion of using a dilute solution of strong acid HCl as an even better catalyst for given reaction is to be criticized.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

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Answer 4

Question

Chapter 11, Problem 11.70AP

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the given reaction is to be stated. The role of weak acid ammonium chloride is also to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the reaction of aziridine requires a weak acid is to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

The suggestion of using a dilute solution of strong acid HCl as an even better catalyst for given reaction is to be criticized.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

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Answer 5

Chapter 11, Problem 11.70AP

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the given reaction is to be stated. The role of weak acid ammonium chloride is also to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the reaction of aziridine requires a weak acid is to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Interpretation Introduction

(b)

Interpretation:

The suggestion of using a dilute solution of strong acid HCl as an even better catalyst for given reaction is to be criticized.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Answer 6

Chapter 11, Problem 11.70AP

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the given reaction is to be stated. The role of weak acid ammonium chloride is also to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Answer 7

Chapter 11, Problem 11.70AP

Interpretation Introduction

(a)

Interpretation:

The curved-arrow mechanism for the given reaction is to be stated. The role of weak acid ammonium chloride is also to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Answer 8

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the reaction of aziridine requires a weak acid is to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Answer 9

Interpretation Introduction

(b)

Interpretation:

An explanation as to why the reaction of aziridine requires a weak acid is to be stated.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Answer 10

Interpretation Introduction

(b)

Interpretation:

The suggestion of using a dilute solution of strong acid HCl as an even better catalyst for given reaction is to be criticized.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Answer 11

Interpretation Introduction

(b)

Interpretation:

The suggestion of using a dilute solution of strong acid HCl as an even better catalyst for given reaction is to be criticized.

Concept introduction:

The nitrogen groups are not good leaving groups in the form of negatively charged nitrogen because of stronger basic nature. Even if the ring strain is removed still that is not enough for nitrogen to leave as negative ion. Therefore, acid is used to protonate nitrogen before its elimination so that it will leave as neutral nitrogen.

Answer 12

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Answer 13

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Answer 14

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Answer 15

Ch. 11 - Prob. 11.1P Ch. 11 - Prob. 11.2P Ch. 11 - Prob. 11.3P Ch. 11 - Prob. 11.4P Ch. 11 - Prob. 11.5P Ch. 11 - Prob. 11.6P Ch. 11 - Prob. 11.7P Ch. 11 - Prob. 11.8P Ch. 11 - Prob. 11.9P Ch. 11 - Prob. 11.10P

Solution Summary: The author explains the curved-arrow mechanism for the reaction of aziridine, and the role of weak acid ammonium chloride.

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Chapter 11 Solutions