During the Reimer-Tiemann reaction, phenol is converted to salicylaldehyde using chloroform () and a — Alcohols Phenols and Ethers Chemistry Question
Question
During the Reimer-Tiemann reaction, phenol is converted to salicylaldehyde using chloroform ($CHCl_3$) and aqueous $NaOH$. What is the specific electrophilic intermediate generated in situ that attacks the aromatic ring?
Answer: B
💡 Solution & Explanation
In the Reimer-Tiemann reaction, the strong base ($NaOH$) deprotonates chloroform, followed by alpha-elimination of a chloride ion to generate dichlorocarbene ($:CCl_2$). This neutral, electron-deficient species acts as the active electrophile attacking the electron-rich phenoxide ring.
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