The aromatic compounds bromobenzene, toluene, phenol, aniline, nitrobenzene and p-bromotoluene are to be ranked in the expected order of their reactivity towards Friedal-Crafts alkylation. Which of them are unreactive is also to be stated. Concept introduction: Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain a meta directing substituent group are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene. As an exception, the aromatic rings that are either substituted by a strongly electron-withdrawing groups such as carbonyl or basic amino group that can be protonated do not react in Friedal crafts reaction, as they deactivate the ring. To rank: The aromatic compounds bromobenzene, toluene, phenol, aniline, nitrobenzene and p-bromotoluene in the expected order of their reactivity towards Friedal-Crafts alkylation. Further to state which of them are unreactive.

Question

A. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?

Answer 1

Question

Chapter 16.SE, Problem 52AP

Interpretation Introduction

Interpretation:

The aromatic compounds bromobenzene, toluene, phenol, aniline, nitrobenzene and p-bromotoluene are to be ranked in the expected order of their reactivity towards Friedal-Crafts alkylation. Which of them are unreactive is also to be stated.

Concept introduction:

Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain a meta directing substituent group are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.

As an exception, the aromatic rings that are either substituted by a strongly electron-withdrawing groups such as carbonyl or basic amino group that can be protonated do not react in Friedal crafts reaction, as they deactivate the ring.

To rank:

The aromatic compounds bromobenzene, toluene, phenol, aniline, nitrobenzene and p-bromotoluene in the expected order of their reactivity towards Friedal-Crafts alkylation. Further to state which of them are unreactive.

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A. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?

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