In the Reimer-Tiemann reaction, phenol is heated with chloroform and aqueous to yield salicylaldehyde as the major product. What is the active electrophilic species generated in situ that attacks the

Question

In the Reimer-Tiemann reaction, phenol is heated with chloroform and aqueous $NaOH$ to yield salicylaldehyde as the major product. What is the active electrophilic species generated in situ that attacks the phenoxide ring?

Prashant Kotian · Accepted Answer

Correct answer: C. In the highly alkaline medium, chloroform () is deprotonated to form the trichloromethyl anion (), which rapidly undergoes alpha-elimination of a chloride ion to generate the neutral, electron-deficient dichlorocarbene (). This neutral singlet carbene acts as the highly reactive electrophile that attacks the electron-rich phenoxide ring.

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