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.

Question

34. Give the expected major product of each of the following reactions. Conc. HI a. CH3CH2CH2OH b. (CH3)2CHCH2CH2OH Conc. HBr H Conc. HI C. OH Conc.HCI d. (CH3CH2)3COH

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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