Question

Sort the following compounds by their reactivity toward electrophilic aromatic substitution.

Sort the following compounds by their reactivity toward electrophilic aromatic substitution.

Answer 1

Concepts and reason

The concept used to solve this problem is the concept of ${\rm{EAS}}$ (electrophilic aromatic substitution). The electrophilic aromatic substitution represents an organic reaction, which is characterized by the replacement of an atom attached to the aromatic ring (usually benzene) by an electrophile.

Fundamentals

In the ${\rm{EAS}}$ , the aromatic ring (usually benzene) acts as a nucleophile and replaces a substituent atom with an electrophile. It means benzene tends to donate electrons from inside its ring. Thus, benzene become less reactive in the ${\rm{EAS}}$ when electron-withdrawing groups (deactivating groups) are attached with it. On the other hand, the ring become more activating towards the ${\rm{EAS}}$ when electron-donating group is attached with it.

The functional group present in the aniline and toluene activates the ring toward ${\rm{EAS}}$ . On the other hand, the functional group attached with the fluorobenzene, nitrobenzene and acetophenone deactivates the ring towards the ${\rm{EAS}}$ .

The compounds can be sorted by their reactivity towards electrophilic aromatic substitution in the following order:

Ans:

The compounds can be sorted by their reactivity towards the ${\rm{EAS}}$ in the following order: