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← IIT-JEE 2007 · Paper 2
ChemistrySingle correct+4 / -1Question 40 of 66

IIT-JEE 2007 · Paper 2, Chemistry question 40

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.)

The electrophile in this reaction is

Choose one option
Answer and worked solution

Official answer: C

The electrophile is dichlorocarbene, formed by α-elimination:
CHClX3+OHX−→CClX3X−+HX2O,CClX3X−→:CClX2+ClX−.\ce{CHCl3 + OH- -> CCl3- + H2O},\qquad\ce{CCl3- -> :CCl2 + Cl-}.
The electron-deficient carbene attacks the phenoxide ring ortho to O⁻.

(C)