9.8 Accomplish the following conversions: (i) Nitrobenzene to benzoic acid (ii) Benzene to m-bromophenol (iii) Benzoic acid to aniline (iv) Aniline to 2,4,6-tribromofluorobenzene (v) Benzyl chloride to 2-phenylethanamine (vi) Chlorobenzene to p-chloroaniline (vii) Aniline to p-bromoaniline (viii) Benzamide to toluene (ix) Aniline to benzyl alcohol.

7.23 Give IUPAC names of the following ethers: 7.24 Write the names of reagents and equations for the preparation of the following ethers by Williamson’s synthesis: (i) 1-Propoxypropane (ii) Ethoxybenzene (iii) 2-Methoxy-2-methylpropane (iv) 1-Methoxyethane 7.25 Illustrate with examples the limitations of Williamson synthesis for the preparation of certain types of ethers. 7.26 How is 1-propoxypropane synthesised from propan-1-ol? Write mechanism of this reaction. 7.27 Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give reason. 7.28 Write the equation of the reaction of hydrogen iodide with: (i) 1-propoxypropane (ii) methoxybenzene and (iii) benzyl ethyl ether. 7.29 Explain the fact that in aryl alkyl ethers (i) the alkoxy group activates the benzene ring towards electrophilic substitution and (ii) it directs the incoming substituents to ortho and para positions in benzene ring. 7.30 Write the mechanism of the reaction of HI with methoxymethane. 7.31 Write equations of the following reactions: (i) Friedel-Crafts reaction – alkylation of anisole. (ii) Nitration of anisole. (iii) Bromination of anisole in ethanoic acid medium. (iv) Friedel-Craft’s acetylation of anisole. 7.32 Show how would you synthesise the following alcohols from appropriate alkenes? CH3 OH (i) OH (ii) OH (iii) (iv) OH 7.33 When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place: Give a mechanism for this reaction. (Hint : The secondary carbocation formed in step II rearranges to a more stable tertiary carbocation by a hydride ion shift from 3rd carbon atom. Chemistry 224 Reprint 2025-26 Answers to Some Intext Questions 7.1 Primary alcohols (i), (ii), (iii) Secondary alcohols (iv) and (v) Tertiary alcohols (vi) 7.2 Allylic alcohols (ii) and (vi) 7.3 (i) 4-Chloro-3-ethyl-2-(1-methylethyl)-butan-1-ol (ii) 2, 5-Dimethylhexane-1,3-diol (iii) 3-Bromocyclohexanol (iv) Hex-1-en-3-ol (v) 2-Bromo-3-methylbut-2-en-1-ol 7.4 OH CH2 C OCH3 7.5 (i) CH3 CH CH3 (ii) O OH (iii) CH3 CH2 CH CH2 OH CH3 7.7 (i) 1-Methylcyclohexene (ii) A Mixture of but-1-ene and but-2-ene. But-2-ene is the major product formed due to rearrangement to give secondary carbocation.

6.22 What happens when (i) n-butyl chloride is treated with alcoholic KOH, (ii) bromobenzene is treated with Mg in the presence of dry ether, (iii) chlorobenzene is subjected to hydrolysis, (iv) ethyl chloride is treated with aqueous KOH, (v) methyl bromide is treated with sodium in the presence of dry ether, (vi) methyl chloride is treated with KCN? Answers to Some Intext Questions 6.1 6.2 (i) H2SO4 cannot be used along with KI in the conversion of an alcohol to an alkyl iodide as it converts KI to corresponding acid, HI which is then oxidised by it to I2. 6.3 (i) ClCH2CH2CH2Cl (ii) ClCH2CHClCH3 (iii) Cl2CHCH2CH3 (iv) CH3CCl2CH3 191 Haloalkanes and Haloarenes Reprint 2025-26