In the Reimer-Tiemann reaction, phenol is refluxed with chloroform and aqueous to yield salicylaldeh — Aromatic Hydrocarbons Chemistry Question
Question
In the Reimer-Tiemann reaction, phenol is refluxed with chloroform and aqueous $NaOH$ to yield salicylaldehyde. What is the active, neutral electrophilic species that attacks the phenoxide ring?
Answer: A
💡 Solution & Explanation
Chloroform is deprotonated by the strong base to form the trichloromethyl anion, which rapidly undergoes alpha-elimination of a chloride ion to generate the neutral, electron-deficient dichlorocarbene ($:CCl_2$).
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