Match List-I (organic transformation) with List-II (reagents) and choose the correct option. List-I A. \ce{C6H6 -> C6H5OH} (benzene to phenol) B. \ce{CH3COOH -> CH3CH2OH} C. \ce{CH3CH2CH2OH -> CH3CH=CH2} D. \ce{C6H5CH(CH3)2 -> C6H5OH} (cumene to phenol) List-II (I) (i) Oleum; (ii) \ce{NaOH}, heat; (iii) \ce{H+} (II) (i) \ce{O2}; (ii) \ce{H2O}/\ce{H+} (III) (i) \ce{CH3OH}, \ce{H+}; (ii) \ce{H2}, catalyst (IV) (i) conc. \ce{H2SO4}, heat; (ii) \ce{H+}/\ce{H2O}

Solution & Explanation

\textbf{Answer:} (B) A-II, B-III, C-IV, D-I \textbf{Solution:} A. Phenol from benzene/cumene via aerial oxidation — the cumene process uses (i) \ce{O2} then (ii) \ce{H2O}/\ce{H+}, which hydrolyses cumene hydroperoxide to phenol and acetone. So A matches (II). B. Carboxylic acid to alcohol: \ce{CH3COOH} is first esterified with \ce{CH3OH}/\ce{H+} and the ester is then reduced with \ce{H2}/catalyst to \ce{CH3CH2OH}. So B matches (III). C. Dehydration of 1-propanol to propene needs conc. \ce{H2SO4}, heat; the \ce{H+}/\ce{H2O} step represents the acid-catalysed mechanism. So C matches (IV). D. Phenol via the benzenesulphonic-acid route: (i) oleum (sulphonation), (ii) \ce{NaOH}, heat (alkali fusion to sodium phenoxide), (iii) \ce{H+} (acidification). So D matches (I). Hence A-II, B-III, C-IV, D-I.