Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

Benzene ring in phenol is expected to give the characteristic substitution or replacement reactions, i.e., halogenation, nitration, sulphonation, alkylation, etc. In these reactions, the attacking reagent is electrophile. The phenolic group activates the ortho and para positions in the ring due to conjugation. Disubstitution reactions are quite fast as the electron density in the ring has increased considerably. Phenols do not respond to nucleophilic substitution reactions as it is influenced by phenolic group.

Minor product in the above reaction is:

Options:

A

B

A and B in same quantity

Cannot be determined

Correct Answer:

A

Explanation:

The correct answer is (1) \(A\)

The reaction of chlorobenzene with acetyl chloride in presence of \(AlCl_3\) can also be called as Freidel – Crafts acylation of chlorobenzene.

The Friedel–Crafts reaction is called an organic coupling reaction.

This is because, in the Friedel–Crafts reaction, an organic aromatic substitution occurs which leads to attachment of a substituent to the aromatic ring.

For this reaction, \(AlCl_3\) is used as a catalyst. The role of the catalyst is to extract chlorine atoms from the reactant and generate an electrophile.

Friedel – Crafts reaction is of 2 types - Friedel–Crafts alkylation and Friedel–Crafts acylation.

Friedel-Crafts acylation is a reaction in which the addition of an acyl group to an aromatic ring takes place. The reaction will lead to the aromatic ring being transformed into a ketone.

The \(Cl\) atom in Chlorobenzene is an ortho-para directing group. This is because \(Cl\) has a lone pair. Therefore, in the resonating structures of chlorobenzene, the electrons will be delocalized into the ring and the electron density on ortho and para position will be increased. The electron density will be more at the ortho and para positions as there are resonating structures in which the negative charge is on the ortho para positions.

Hence, the Friedel–Crafts acylation of chlorobenzene will yield us both ortho and para products.

Therefore, the reaction of chlorobenzene with acetyl chloride in the presence of \(AlCl_3\), will yield the products - 2-Chloro Acetophenone and 4-Chloro Acetophenone.