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

Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.) m-Chlorobenzoic acid

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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