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← IIT-JEE 2007 · Paper 2
ChemistrySingle correct+4 / -1Question 39 of 66

IIT-JEE 2007 · Paper 2, Chemistry question 39

Passage

Paragraph for Question Nos. 39 to 41

Reimer-Tiemann reaction introduces an aldehyde group, on to the aromatic ring of phenol, ortho to the hydroxyl group. This reaction involves electrophilic aromatic substitution. This is a general method for the synthesis of substituted salicylaldehydes as depicted below.

(Scheme: 4-methylphenol (p-cresol) → intermediate I → II → III, where III is 2-hydroxy-5-methylbenzaldehyde; the last step is acidification.)

(The paragraph is not printed in the official archive copy (which reproduces only the questions with their answers); its text is restored from the JEE 2007 question paper.)

Which one of the following reagents is used in the above reaction?

Choose one option
Answer and worked solution

Official answer: C

Reimer-Tiemann conditions: chloroform with aqueous NaOH. Hydroxide removes a proton from CHClX3\ce{CHCl3}, and the trichloromethyl anion loses chloride to give dichlorocarbene.

(C)