JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Phenol treated with chloroform in presence of sodium hydroxide, which further hydrolyzed in presence of an acid results
- ASalicylic acid
- BBenzene-1,2-diol
- C2-Hydroxybenzaldehyde
- DBenzene-1,3-diol
View written solutionFree
Correct answer: C
- Identify the reaction
Phenol treated with chloroform () in the presence of sodium hydroxide (), followed by hydrolysis/acidification, is the Reimer–Tiemann reaction.
- What happens in Reimer–Tiemann reaction?
In this reaction, phenol first forms phenoxide ion in basic medium:
Chloroform in strong base generates dichlorocarbene (), which acts as the electrophile.
The formyl group is introduced mainly at the ortho position of phenol, and after hydrolysis gives o-hydroxybenzaldehyde.
- Main product formed
Thus, phenol gives:
This compound is 2-hydroxybenzaldehyde (also called salicylaldehyde).
- Check the options
- A: Salicylic acid This is formed in the Kolbe reaction using , not here. Incorrect.
- B: Benzene-1,2-diol Catechol, not formed in Reimer–Tiemann reaction. Incorrect.
- C: 2-Hydroxybenzaldehyde Correct.
- D: Benzene-1,3-diol Resorcinol, not formed here. Incorrect.
- Final answer
The product obtained is 2-hydroxybenzaldehyde.
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