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Chapter 16: Q33E (page 524)

Triphenylmethane can be prepared by reaction of benzene and chloroform in the presence of AlCl3. Propose a mechanism for the reaction.

Short Answer

Expert verified

Mechanism followed as shown below.

Step by step solution

01

Reaction of chloroform with aluminium chloride 

When a reaction of chloroform occurs with aluminium chloride, it leads to the formation of dichloro carbocation which acts as an electrophile in reaction with the benzene.

Formation of Electrophile

02

Reaction of benzene with an electrophile

When the dichloro carbocation reacts with benzene, one of the double bond of the aromatic ring breaks and addition of ring occurs followed by the reaction with aluminium chloride which protonates the hydrogen. As a result, the ring regains its aromaticity and the formation of dichloro methyl occurs as shown below.

Formation of (dicholromethyl) benzene

03

Formation of triphenylmethane

Similarly, the reaction of the dicholromethyl benzene with 2 moles of benzene in the presence of aluminium trichloride is shown below

Formation of Triphenylmethane

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