(a) (i) How will you bring about the following conversions : (I) Bromobenzene to 1-phenylethanol (II) Benzene to m-nitroacetophenone (ii) An organic compound with the molecular formula $\text{C}_8\text{H}_8\text{O}$ forms 2,4-DNP derivative, reduces Tollens' reagent and undergoes Cannizzaro reaction. On vigorous oxidation with acidic or alkaline $\text{KMnO}_4$ it gives Benzene-1,2-dicarboxylic acid. Identify the compound and write the products when it undergoes Cannizzaro reaction. (iii) Arrange the following compounds in increasing order of their acid strength : $\text{C}_6\text{H}_5\text{COOH}, \text{O}_2\text{N} - \text{CH}_2 - \text{COOH}, \text{CF}_3 - \text{COOH}, \text{HCOOH} OR (b) (i) Write the products formed when benzaldehyde reacts with the following reagents : (I) 2,4-Dinitrophenylhydrazine (II) Acetophenone in the presence of dilute $\text{NaOH}$ followed by heating (ii) Give reasons for the following : (I) Benzoic acid does not undergo Friedel-Crafts reaction. (II) Carboxylic acids have higher boiling point than alcohols of comparable molecular mass. (iii) Write simple chemical test to distinguish between propanal and propanone.