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NEET CHEMISTRYHydrocarbonsMedium

Question

The reaction of toluene with Cl2Cl_2 in presence of FeCl3FeCl_3 gives ‘X' and the reaction in presence of light gives 'Y'. 'X' and 'Y' are respectively:

A

X= Benzal chloride, Y= o-chlorotoluene

B

X= m-chlorotoluene, Y= p-chlorotoluene

C

X= o and p-chlorotoluene, Y= trichloromethyl benzene

D

X= Benzyl chloride, Y= m-chlorotoluene

Step-by-Step Solution

  1. Reaction producing X (Electrophilic Aromatic Substitution): When toluene reacts with chlorine (Cl2Cl_2) in the presence of a Lewis acid catalyst like iron(III) chloride (FeCl3FeCl_3) or iron (FeFe), an electrophilic substitution reaction occurs on the benzene ring. The methyl group (CH3-CH_3) is an ortho-para directing group. Therefore, the entering chlorine atom attacks the ortho and para positions relative to the methyl group, yielding a mixture of o-chlorotoluene and p-chlorotoluene . C6H5CH3+Cl2FeCl3oClC6H4CH3+pClC6H4CH3C_6H_5CH_3 + Cl_2 \xrightarrow{FeCl_3} o-ClC_6H_4CH_3 + p-ClC_6H_4CH_3

  2. Reaction producing Y (Free Radical Substitution): When the reaction is carried out in the presence of light (hνh\nu) or heat, the conditions favour a free radical mechanism. This leads to substitution in the alkyl side chain (benzylic position) rather than the ring, similar to the halogenation of alkanes . The hydrogen atoms of the methyl group are replaced by chlorine atoms. Depending on the extent of reaction, mono-, di-, or tri-chlorinated products (benzyl chloride, benzal chloride, or benzotrichloride) are formed. Option 3 specifies trichloromethyl benzene (benzotrichloride), which is the product of exhaustive side-chain chlorination. C6H5CH3+3Cl2hνC6H5CCl3+3HClC_6H_5CH_3 + 3Cl_2 \xrightarrow{h\nu} C_6H_5CCl_3 + 3HCl

  3. Conclusion: X is the mixture of ring-substituted isomers (o and p-chlorotoluene), and Y is the side-chain substituted product (trichloromethyl benzene).

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Hydrocarbons. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYHydrocarbonsreactiontoluenepresencereactionpresence

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