The observation that the N,N,N-trimethylammonium group –N(CH 3 ) 3 , though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained. Concept introduction: In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar. If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles. The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid. To explain: The observation that the N,N,N-trimethylammonium group –N(CH 3 ) 3 , though a meta directing deactivator does not exhibit electron withdrawing resonance effect.

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Answer 1

Question

Chapter 16.SE, Problem 31MP

Interpretation Introduction

Interpretation:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained.

Concept introduction:

In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar.

If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles.

The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid.

To explain:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect.

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Please help me with number 1-3. Thank you so much.

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Answer 2

Question

Chapter 16.SE, Problem 31MP

Interpretation Introduction

Interpretation:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained.

Concept introduction:

In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar.

If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles.

The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid.

To explain:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect.

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Answer 3

Question

Chapter 16.SE, Problem 31MP

Interpretation Introduction

Interpretation:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained.

Concept introduction:

In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar.

If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles.

The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid.

To explain:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect.

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Answer 4

Question

Chapter 16.SE, Problem 31MP

Interpretation Introduction

Interpretation:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained.

Concept introduction:

In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar.

If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles.

The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid.

To explain:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect.

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Answer 5

Chapter 16.SE, Problem 31MP

Interpretation Introduction

Interpretation:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained.

Concept introduction:

In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar.

If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles.

The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid.

To explain:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect.

Answer 6

Chapter 16.SE, Problem 31MP

Interpretation Introduction

Interpretation:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained.

Concept introduction:

In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar.

If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles.

The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid.

To explain:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect.

Answer 7

Chapter 16.SE, Problem 31MP

Interpretation Introduction

Interpretation:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect is to be explained.

Concept introduction:

In planar molecules the overlapping of p orbitals on adjacent carbon atoms takes place leading to the formation of different resonance forms. Resonance is not possible if the molecule is not co-planar.

If the group already present on the benzene ring is electron withdrawing by resonance and/or inductive effect it will deactivate the ring towards electrophiles.

The stability of a resonance hybrid depends on the number of stable individual resonance forms that contribute to the hybrid. More the number, the more stable is the hybrid.

To explain:

The observation that the N,N,N-trimethylammonium group –N(CH₃)₃, though a meta directing deactivator does not exhibit electron withdrawing resonance effect.

Answer 8

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Answer 19

Ch. 16.1 - Prob. 1P Ch. 16.2 - Propose a mechanism for the electrophilic...Ch. 16.2 - How many products might be formed on chlorination...Ch. 16.2 - When benzene is treated with D2SÅª4. deuterium...Ch. 16.3 - Prob. 5P Ch. 16.3 - What is the major monosubstitution product from...Ch. 16.3 - Identify the carboxylic acid chloride that might...Ch. 16.4 - Rank the compounds in each of the following groups...Ch. 16.4 - Predict the major products of the following...Ch. 16.4 - Prob. 10P

Solution Summary: The author explains that nitrogen deactivates the ring towards elelctrophiles since it has an electron withdrawing inductive effect.

Chapter 16 Solutions