Intext 10.2 Why is sulphuric acid not used during the reaction of alcohols with KI? (0.3 Write structures of different dihalogen derivatives of propane. (4 Among the isomeric alkanes of molecular formula C,H,,, identify the one that on photochemical chlorination yields _19-A single monochloride. (i) Three isomeric monochlorides. i) Four isomeric monochlorides. 10.§Draw the structures of major monohalo products in each of the following reactions: CH,¢ CH, oe m “br heat or, | ) + SOCl, —> wer oe | CHOH CH, “4 | a) Cr + Ho Ay “i ae ‘+ HI —> OH FA heat _ ) CH,CHBr + Nal —> Cryta, $9 O + Br,Exercises and classi! ‘ -10. Name the following halides according to TUPAC eee cal ae them alkyl, allyl, benzyl (primary, secondary, tertiary), viny! @ (CHJ,CHCH(CI)CH, (i) CH,CH,CH(CH,)CH(C,HJCI (ii) CH,CH,C(CH,),CH,1 (iv) (CH),CCH,CHIBNC,H, (v)_ CH,CH(CH,)CH(BNCH,, (vi) CH,C(C,H,),CH,Br (vii) CH,C(CI(C,HCH,CH, (viii), CH,CH=C{CI)CH,CHICH,), (ix) CH,CH=CHC(Br)(CHJ), (x) p-CIC,H,CH,CH(CH,), (x) m-CICH,C,H,CH,C(CH,), (ii) o-Br-C,H,CH(CH,)CH,CH, 1 Give the IUPAC names of the following compounds: (@ CH,CH(CNCH(BNCH, (i) CHF,CBrCIF (ii) CICH,C=CCH,Br Gv) (CCL),CCI (¥) CH,C(p-CIC,H),CHBACH, (vi) (CH,),CCH=CIC,H,-p 10.97" Write the structures of the following organic halogen compounds. (i) 2-Chloro-3-methylpentane (iii). 1-Chloro-4-ethyleyclohexane (iv) 2-@-Chiorophenyl)-1-iodooctane {v) Perfluorobenzene (vi) 4-tert-Butyl- 3-lodoheptane 3 (vii) 1-Bromo-4-sec-butyl-2-methylbenzene (viii) 1,4-Dibromobut-2-ene (i) p-Bromochlorobenzenewa Which one of the following has the highest dipole moment? §) CHCl, (i) CHI, Gy cor, : 4 hydrocarbon CH, does not react with chlorine in dark but gives a single monochloro compound C,H,CI in bright sunlight. Identify the hydrocarbon. Write the Isomers of the compound having formula C,H,Br. 49c7 Write the equations f Preparation of 1-iodobutane from ak @Tbutanol "\s)-Teniowboonne uty But-1-ene. oe wna are ambident nucleophiles? Explain with an example. 49-6°wnieh compound in each of the following pairs will react faster in ,2 reaction ( with “OH? a yea or (CH, wea ir CH,Cl 10.0 Predict./all the~alkenes that would be formed by dehydrohalogenation of the ~ following halides with sodium ethokide in ethanol and identify the major alkene: ww “Bromo- l-methylcyclohexane ¢{i) 2-Chloro-2-methylbutane ) 2,2,3-Trimethyl-3-bromopentane. 10.11 How will you bring about the following conversions? i) Ethanol to but-L-yne oy) thane to beeuaeteens 1] Propene to eee (ivf Toluené to benzyl alcohol 6) Propene to_propyne (yi Ethanol to ethyl Muoride (vii) Bromomethane ‘to propanone HB Bien (0 but-2-ene "(oF 1-Chlorobuane to moctane € Benzene to biphenyl. “12 Explain why (thea i) alkyl halides, though polar, are imm pole moment of chlorobenzene is lower than that of cyclohexyl chloride? ible with water? 4iff) Grignard reagents should be prepared under anhydrous conditions? YA3 Give the uses of freon 12, DDT, carbon tetrachloride and iodoform. AO.1. rite the structure of the major organic product in each of the following reactions: Z ~ 1 cH,cH,0 cl + Nar —29etone, CHy~ CM, - tm, —L heat Am (onycrr « won and, ene CLCMs) a heat we H,CH(Br)CH,CH, + Nao —WwWater Uny- on (ony 1 (iy €H,CH,Br + KCN eqenencl CMs th, LN OYEHONa + CHCl ———> ig —O CMs (i)/CH,CH,CH,OH + SOCI, ie then, cu,- ‘ fuv-cn,cu,cu = CH, + HBr —Peroxce en on ONY, a CH,CH = C(CH, + HBr ————">_ Cu, Ck — CU) 4948 Write the mechanism of the following reaction: | EtOH-H,O. nBuCN Br + KCN _EtOHTLO , (16 Arrange the compounds of each set in order of reactivity towards S,2 displacement: _Atf 2-Bromo-2-methylbutane, 1-Bromopentane, 2-Bromopentane j OB 4 jbutane. 2-Bromo-2-methylbutane, 3-Bromo-2-methylbutane ” 1-Bromo-: “a methylbuta!(ii) 1-Bromobutane, 1-Bromo-2,2-dimethylpropane, 1-Bromio-2- -methylbutang,, 1-Bromo-3-methylbutane. - 3 £7 Out of C,HjCH,CI and C,H,CHCIC,H,, which is more easily hydrolysed by aqueotis KOH. 1918 p-Dichlorobenizene has higher m.p. and solul Discuss. vio.19 amen following conversions can. be carried out? bility thah those of o- ahd i-isoin ‘opene to propan-1-ol Ethanol to but-l-yneg,. at “(iy 1-Bromopropane to 2-bromopropane\_——~ ) Toluene to benzyl alcohol —\———; Lewy ‘Benzene to 4-bromonitroberizene \—— fenzyl alcohol to 2-phenylethanoie acid ~~ phi) Ethanol to propanenitrile \-— ar iline to chlorobenzene. ~~ 2-Chlorobutane to 3, ‘s-illinethythdcind7" <{ 2-Methyl-1-propene to s-chiovo-2-methyipiopiina_ 7 thyl chloride to propanoic acid) ——! Bh be -ene to n-butyliodide_——~ «bai 2-Chloropropane to 1-propanol (xiy) Isopropyl alcohol to iodoform hy Chlorobenzene to p-nitrophenol ~~ -baxff 2-Bromopropane to, 1-bromopropane \” (xvi Chloroethane to bile C Br Benzene to diphenyl, (ix) tert-Butyl bromide to isobutyl bromide Aniline to phenylisocyanide.—~ “20 The treatment of alkyl chlorides with aqueous KOH leads to the formation of alcohols but in the presence of alcoholic KOH, alkenes = are major products. Explain, Primary alkyl halide C,H,Br (a) reacted with alcoholic KOH to give compound (b). Compound (b) is reacted with HBr to give (c) which is an isomer of (a). When {a) is reacted with sodium metal it gives compound (d).'C,H,, which is different from the compound formed when n-butyl bromide is reacted with sodium. _Give the structural formula of (a) and write the equations for all, the reactions. / 10-22 What happens when (Sr butyl chloride is treated with alcoholic KOH, Ad tmanes is treated with Mg in the presence of dry ether, ) chlorobenzene is subjected to hydrolysis, (iy¥ethyl chloride is treated with aqueous KOH, m4 methyl bromide is treated with sodium in ‘the Presence of dry ether. (_ waretny! chloride is treated with KCN?