In the Reimer-Tiemann reaction, phenol is refluxed with chloroform and aqueous NaOH to yield salicyl — 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: C
💡 Solution & Explanation
Chloroform is deprotonated to form the trichloromethyl anion, which rapidly undergoes alpha-elimination of a chloride ion to generate neutral, highly reactive, electron-deficient dichlorocarbene (:CCl2).
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