Question:
When phenol is treated with chloroform (\(\text{CHCl}_3\)) in the presence of an aqueous sodium hydroxide solution followed by acidification, a prominent aromatic aldehyde is generated. What is the name of this organic reaction?
When phenol is treated with chloroform (\(\text{CHCl}_3\)) in the presence of an aqueous sodium hydroxide solution followed by acidification, a prominent aromatic aldehyde is generated. What is the name of this organic reaction?
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Use the reagents to easily distinguish between these similar reactions of phenol:
Phenol + \(\text{CHCl}_3 / \text{NaOH} \rightarrow\) Salicylaldehyde (Reimer-Tiemann).
Phenol + \(\text{CO}_2 / \text{NaOH} \rightarrow\) Salicylic Acid (Kolbe's).
Updated On: May 19, 2026
- Kolbe's Reaction
- Reimer-Tiemann Reaction
- Rosenmund Reduction
- Friedel-Crafts Acylation
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The Correct Option is B
Solution and Explanation
Concept:
Treating phenol with chloroform in an alkaline medium introduces a formyl functional group (\(-\text{CHO}\)) ortho to the hydroxyl group. This transformation proceeds via a highly reactive dichlorocarbene (\(:\text{CCl}_2\)) electrophilic intermediate.
Step 1: Trace the reaction mechanism steps.
Phenol reacts with \(\text{NaOH}\) and \(\text{CHCl}_3\) to produce an intermediate benzal chloride derivative on the ring. Subsequent alkaline hydrolysis and acidification yield 2-hydroxybenzaldehyde, commonly known as salicylaldehyde. \[ \text{C}_6\text{H}_5\text{OH} \xrightarrow[\text{(ii) H}^+]{\text{(i) CHCl}_3 + \text{NaOH}} o\text{-HO--C}_6\text{H}_4\text{--CHO} \] This classic synthetic transformation is named the Reimer-Tiemann reaction.
Step 1: Trace the reaction mechanism steps.
Phenol reacts with \(\text{NaOH}\) and \(\text{CHCl}_3\) to produce an intermediate benzal chloride derivative on the ring. Subsequent alkaline hydrolysis and acidification yield 2-hydroxybenzaldehyde, commonly known as salicylaldehyde. \[ \text{C}_6\text{H}_5\text{OH} \xrightarrow[\text{(ii) H}^+]{\text{(i) CHCl}_3 + \text{NaOH}} o\text{-HO--C}_6\text{H}_4\text{--CHO} \] This classic synthetic transformation is named the Reimer-Tiemann reaction.
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