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← JEE Advanced 2013 · Paper 2
ChemistryMultiple correct+3 / -1Question 26 of 60

JEE Advanced 2013 · Paper 2, Chemistry question 26

In the following reaction, the product(s) formed is(are)

p-Cresol (4-methylphenol) treated with CHCl₃ and OH⁻ gives ?Candidate products: P 2-hydroxy-5-methylbenzene-1,3-dicarbaldehyde; Q 4-(dichloromethyl)-4-methylcyclohexa-2,5-dien-1-one; R 4-(dichloromethyl)-4-methylcyclohexa-2,5-dien-1-ol; S 2-hydroxy-5-methylbenzaldehyde.
Choose one or more options
Answer and worked solution

Official answer: B, D

Reimer-Tiemann on p-cresol. Dichlorocarbene attacks the phenoxide mainly ortho to O⁻, giving 2-hydroxy-5-methylbenzaldehyde (S, major).

Abnormal product. Attack at the para carbon, which carries the methyl, cannot rearomatise; it gives the dienone 4-(dichloromethyl)-4-methylcyclohexa-2,5-dienone (Q, minor).

(B), (D)

Topics:PhenolsNamed reactions
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