JEE Main · 2006 · 30 Apr 2006 · Offline · Alcohols Phenols and Ethers

The electrophile involved in the above reaction is

(A)dichloromethyl cation $(C \oplus HCl_{2})$
(B)dichlorocarbene(: $CCl_{2}$ )✓ Correct
(C)trichloromethyl anion $(CCl_{3} ⊖)$
(D)formyl cation $(C + HO) (\oplus)$

Answer: (B)

Solution

The reaction depicted is the Reimer-Tiemann reaction, in which chloroform is first deprotonated by the strong base and then loses chloride to generate the reactive electrophile. That electrophile is dichlorocarbene,

: CC l_{2}

, a neutral, electron-deficient carbon species that attacks the phenolate ring, leading after hydrolysis to the ortho-aldehyde. The electrophile involved is therefore dichlorocarbene,

: CC l_{2}

JEE Main · 2006 · 30 Apr 2006 · Offline · Single correct option

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