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NEET CHEMISTRYMedium

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.

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