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

Curved arrows are used to illustrate the flow of electrons. Using the provided structures, draw the curved arrows that epict the mechanistic steps for the proton transfer between a hydronium ion and a pi bond. Draw any missing organic structures in the empty boxes. Be sure to account for all lone-pairs and charges as well as bond-breaking and bond-making steps. 2 56°F Mostly cloudy F1 Drawing Arrows > Q Search F2 F3 F4 ▷11 H. H : CI: H + Undo Reset Done DELL

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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