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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

Reaction of phenol with chloroform in the presence of dilute sodium hydroxide finally introduces which one of the following functional groups?

A

-CH₂Cl

B

-COOH

C

-CHCl₂

D

-CHO

Step-by-Step Solution

The reaction described is the Reimer-Tiemann reaction.

  1. Reagents: Phenol is treated with chloroform (CHCl3CHCl_3) in the presence of aqueous sodium hydroxide (NaOHNaOH).
  2. Process: An electrophilic substitution occurs on the aromatic ring. The reaction involves a dichlorocarbene (:CCl2:CCl_2) intermediate. The initial product is a benzal chloride derivative which is hydrolysed in the alkaline medium to form an aldehyde group.
  3. Result: The final acidification yields Salicylaldehyde (2-hydroxybenzaldehyde). Thus, an aldehyde group (CHO-CHO) is introduced, predominantly at the ortho position to the phenolic -OH group.

Note: If carbon tetrachloride (CCl4CCl_4) were used instead of chloroform, the reaction would introduce a carboxyl group (COOH-COOH) yielding salicylic acid.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. 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.

CHEMISTRYAlcohols, Phenols and Ethersreactionphenolchloroformpresencedilute

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