MCQEasyJEE 2024Aryl Halides

JEE Chemistry 2024 Question with Solution

Given below are two statements: one is labelled as Assertion AA and the other is labelled as Reason RR: Assertion AA: Aryl halides cannot be prepared by replacement of hydroxyl group of phenol by halogen atom. Reason RR: Phenols react with halogen acids violently.

  • A

    Both AA and RR are true but RR is NOT the correct explanation of AA

  • B

    AA is false but RR is true

  • C

    AA is true but RR is false

  • D

    Both AA and RR are true and RR is the correct explanation of AA

Answer

Correct answer:C

Step-by-step solution

Standard Method

Given: Assertion AA states that aryl halides cannot be prepared by replacement of hydroxyl group of phenol by halogen atom. Reason RR states that phenols react with halogen acids violently.

Find: Which option correctly describes the truth values of AA and RR.

Assertion AA is true. In phenol, the OH-OH group is attached to an aromatic ring, and the bond acquires resonance stabilization with the benzene ring. Because of this, direct replacement of the hydroxyl group by a halogen atom does not occur easily.

Reason RR is false. Phenols do not react violently with halogen acids such as HCl\text{HCl}, HBr\text{HBr}, or HI\text{HI} under normal conditions to give aryl halides by simple replacement of the hydroxyl group.

Therefore, assertion AA is true but reason RR is false. The correct option is C.

Detailed Explanation

Given:

  • Assertion AA: Aryl halides cannot be prepared by replacement of hydroxyl group of phenol by halogen atom.
  • Reason RR: Phenols react with halogen acids violently.

Find: The correct relation between assertion and reason.

  1. Analyze Assertion AA: Phenols have a hydroxyl group attached directly to the benzene ring. The OH-OH group is resonance stabilized, so the CO\text{C}-\text{O} bond is strengthened and is not easily broken for substitution by halide ion.
  2. Hence, direct conversion of phenol into aryl halide by replacing OH-OH with halogen is not feasible by the usual halogen acid method.
  3. Therefore, Assertion AA is true.
  4. Analyze Reason RR: The statement says phenols react violently with halogen acids. This is incorrect. Phenols generally do not undergo such reaction with halogen acids to form aryl halides.
  5. Therefore, Reason RR is false.

A representative statement from the solution is:

Phenol (C6H5OH)+HXNo Reaction\text{Phenol } (\text{C}_6\text{H}_5\text{OH}) + \text{HX} \rightarrow \text{No Reaction}

Thus, the final conclusion is that Assertion AA is true but Reason RR is false, so the correct option is C.

Common mistakes

  • Assuming phenol behaves like an alcohol is incorrect because the hydroxyl group in phenol is attached to an aromatic ring and is resonance stabilized. Do not apply the same substitution logic used for aliphatic alcohols.

  • Thinking that halogen acids readily convert phenol to aryl halides is wrong because phenols do not undergo simple replacement of OH-OH by halogen with HX\text{HX}. Check whether the substrate is aliphatic or aromatic first.

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