9.9 Give the structures of A, B and C in the following reactions: B NaOH  Br 2 C (i) CH 3 CH 2 I NaCN A Partial OHhydrolysis CuCN H 2 O/H  NH 3 (ii) C 6 H 5 N 2 Cl  A  B  C 4 B HNO 2 C (iii) CH 3 CH 2 Br KCN A LiAlH 0  C  2  2 O/H HCl B H C  (iv) C6 H 5 NO 2 Fe/HCl A NaNO273 K 3 A NaOBr B NaNO 2 /HCl C (v) CH 3 COOH NH 2 B C 6 H 5 OH C (vi) C6 H 5 NO 2 Fe/HCl A HNO273K 279 Amines Reprint 2025-26

6.9 Which compound in each of the following pairs will react faster in SN2 reaction with –OH? (i) CH3Br or CH3I (ii) (CH3)3CCl or CH3Cl 6.10 Predict all the alkenes that would be formed by dehydrohalogenation of the following halides with sodium ethoxide in ethanol and identify the major alkene: (i) 1-Bromo-1-methylcyclohexane (ii) 2-Chloro-2-methylbutane (iii) 2,2,3-Trimethyl-3-bromopentane. 6.11 How will you bring about the following conversions? (i) Ethanol to but-1-yne (ii) Ethane to bromoethene (iii) Propene to 1-nitropropane (iv) Toluene to benzyl alcohol (v) Propene to propyne (vi) Ethanol to ethyl fluoride (vii) Bromomethane to propanone (viii) But-1-ene to but-2-ene (ix) 1-Chlorobutane to n-octane (x) Benzene to biphenyl. 6.12 Explain why (i) the dipole moment of chlorobenzene is lower than that of cyclohexyl chloride? (ii) alkyl halides, though polar, are immiscible with water? (iii) Grignard reagents should be prepared under anhydrous conditions? 6.13 Give the uses of freon 12, DDT, carbon tetrachloride and iodoform. 6.14 Write the structure of the major organic product in each of the following reactions: (i) CH3CH2CH2Cl + NaI (ii) (CH3)3CBr + KOH (iii) CH3CH(Br)CH2CH3 + NaOH (iv) CH3CH2Br + KCN (v) C6H5ONa + C2H5Cl (vi) CH3CH2CH2OH + SOCl2 (vii) CH3CH2CH = CH2 + HBr (viii) CH3CH = C(CH3)2 + HBr 6.15 Write the mechanism of the following reaction: nBuBr + KCN nBuCN 6.16 Arrange the compounds of each set in order of reactivity towards SN2 displacement: (i) 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane (ii) 1-Bromo-3-methylbutane, 2-Bromo-2-methylbutane, 2-Bromo-3-methylbutane (iii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromo-2-methylbutane, 1-Bromo-3-methylbutane. 6.17 Out of C6H5CH2Cl and C6H5CHClC6H5, which is more easily hydrolysed by aqueous KOH. 6.18 p-Dichlorobenzene has higher m.p. than those of o- and m-isomers. Discuss. 6.19 How the following conversions can be carried out? (i) Propene to propan-1-ol (ii) Ethanol to but-1-yne (iii) 1-Bromopropane to 2-bromopropane Chemistry 190 Reprint 2025-26 (iv) Toluene to benzyl alcohol (v) Benzene to 4-bromonitrobenzene (vi) Benzyl alcohol to 2-phenylethanoic acid (vii) Ethanol to propanenitrile (viii) Aniline to chlorobenzene (ix) 2-Chlorobutane to 3, 4-dimethylhexane (x) 2-Methyl-1-propene to 2-chloro-2-methylpropane (xi) Ethyl chloride to propanoic acid (xii) But-1-ene to n-butyliodide (xiii) 2-Chloropropane to 1-propanol (xiv) Isopropyl alcohol to iodoform (xv) Chlorobenzene to p-nitrophenol (xvi) 2-Bromopropane to 1-bromopropane (xvii) Chloroethane to butane (xviii) Benzene to diphenyl (xix) tert-Butyl bromide to isobutyl bromide (xx) Aniline to phenylisocyanide

8.17 Complete each synthesis by giving missing starting material, reagent or products