Question

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 (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

Answer 1

The reagents used for the given conversions are as follows:

(i) Propene to propan-1-ol
(a) HBr/ peroxide, (b) aq KOH
(ii) Ethanol to but-1-yne
(a) P, iodine heat (b) alc. KOH, heat (c) bromine, $CC{l}_4$ (d) $NaN{H}_2/liqN{H}_3$ (2 equiv) (e) excess methyl iodide
(iii) 1-Bromopropane to 2-bromopropane
(a) Alc. KOH heat (b) HBr Markovnikoff's addition
(iv) Toluene to benzyl alcohol
(a) Chlorine, sunlight, (b) aq KOH, heat
(v) Benzene to 4-bromonitrobenzene
(a) Bromine, ferric bromide, (b) Conc. $HN{O}_3+$ conc. $H_{2}S{O}_4$
(vi) Benzyl alcohol to 2-phenylethanoic acid
(a) Thionyl chloride (b) alc KCN (c) $H^{+}$ / water
(vii) Ethanol to propanenitrile
(a) P, $I_2$ heat, (b) alc KCN
(viii) Aniline to chlorobenzene
(a) $NaN{O}_2,HCl$ 273-278 K, (b) $CuCl,HCl$ sandmeyer reaction.
(ix) 2-Chlorobutane to 3, 4-dimethylhexane
Na wurtz reaction
(x) 2-Methyl-1-propene to 2-chloro-2-methylpropane
HCl markownikoff's addition
(xi) Ethyl chloride to propanoic acid
(a) Alc KCN (b) $H^{+},H_{2}O$ hydrolysis
(xii) But-1-ene to n-butyliodide
(a) HBr peroxide (b) NaI acetone
(xiii) 2-Chloropropane to 1-propanol
(a) alc. KOH heat, (b) HBr peroxide (c) alc. KOH, heat
(xiv) Isopropyl alcohol to iodoform
$I_2/NaOH$ heat
(xv) Chlorobenzene to p-nitrophenol
(a) Conc. $HN{O}_3$ + conc. $H_{2}S{O}_4$ (b) aq NaOH (15%), 433 K (c) dil HCl
(xvi) 2-Bromopropane to 1-bromopropane
(a) alc KOH heat (b) HBr peroxide.
(xvii) Chloroethane to butane
Na wurtz reaction
(xviii) Benzene to diphenyl
(a) Bromine, ferric bromide (b) Na Dry ether fitting reaction
(xix) tert-Butyl bromide to isobutyl bromide
(a) Alc KOH, heat (b) HBr peroxide
(xx) Aniline to phenylisocyanide
$CHC{l}_3/KOH$ warm