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ChemistrySingle correct+3 / -1Question 36 of 54

JEE Advanced 2017 · Paper 1, Chemistry question 18

Passage

Answer Q.34, Q.35 and Q.36 by appropriately matching the information given in the three columns of the following table.

Columns 1, 2 and 3 contain starting materials, reaction conditions, and type of reactions, respectively.

Column 1 Column 2 Column 3
(I) Toluene (i) NaOH/ BrX2\ce{Br2} (P) Condensation
(II) Acetophenone (ii) BrX2\ce{Br2}/ hνh\nu (Q) Carboxylation
(III) Benzaldehyde (iii) (CHX3CO)X2O\ce{(CH3CO)2O}/ CHX3COOK\ce{CH3COOK} (R) Substitution
(IV) Phenol (iv) NaOH/ COX2\ce{CO2} (S) Haloform

The only CORRECT combination in which the reaction proceeds through radical mechanism is

Choose one option
Answer and worked solution

Official answer: D

Toluene (I) with BrX2/hν\ce{Br2}/h\nu (ii) undergoes free-radical side-chain substitution (R), giving benzyl bromide by a radical chain mechanism.

(D)