Chapter 13 Hydrocarbons ‘Answer (1) More number of a Hydrogen in alkene less is the heat of hydrogenation Correct order of heat of hydrogenation is Or « OF « CE CL 10H 4acH 3acH 3H Answer (4) Half chair is the least stable of cyclohexane with maximum energy. Answer (2) Rate of abstraction of hydrogen is 1: 3.8 : 5 for 19H : 2° H : 3°H respectively. ee AZ Wow A B Cc D 13 3ax2 5x1 16 3 76 5 6 Answer (1) Cc ae voy i Ptraton A) +o) 22 Peenaton, 70 \ Mechanism => 1,4 addition is followed at high temperature (40°C - 80°C) => In irst step formation of most stable carbocation => In 2% step at high temperature less stable carbocation is formed RP 414 Protonation fe (40"c - 80°C) cl A) Major product Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456442) Hydrocarbons 5, Answer (2) ji rs cH—c— er cH,—c = cH, ie aati 6 Answer (2) CH, =n 7. Answer (3) COOH COONa S104 _,2cH, —(CHO), akene 2/20 H H I i c=o o=c = 7 Se a ag e CH, 2 cH’ cH, eae o=c NcH=ch~ H 1, 4 Cyclohexadiene 8. Answer (2) ° =c—cH, or 9, Answer (2) Electrophilic substitution reaction ql cl —= HS0, cl cl SO.H I a — 180, cl cl This product is not possible due to steric crowding Corporate Office : Aakash Tower, 8, Pusa Road, New Del A Solutions (Part-I) O + Naco I Ho'nig Ge —CH.—CH, ene 10005. Phone : 011-47623456Solutions (Parts!) Hydrocarbons 443 10. "1 12. 13, 14, Answer (1) If alkene have more number of a-Hydrogen, lower will be its heat of hydrogenation, greater, will be stability. => Correct order of stability is O-0-O°0 4-a'H 3-a'H 2-a-' 1a and anal tnd and Resonance No Resonance No Resonance No Resonance Answer (3) Chair form of bromo cyclo hexane is the most stable conformer due to absence of steric strain. => When Bromine present at equatorial position then more will be stability. => Stability order is i Weve Olen ‘Answer (1) In Wurtz reaction, free radical mechanism will be followed hence higher is the stability of free radical carbon greater is the rate of formation of alkane. In smaller ring free radical carbon is less stable due to angular strain. Answer (3) There are four monochloro derivatives. Answer (4) Hy /Pd BaSO, —Lindlar's Catalyst It give cis alkene from alkyne Na/NH, (I) > Alkynes on reduction with sodium in liquid ammonia form trans alkene Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-476234564144 Hydrocarbons Solutions (Parts!) HuPa BasO, ne equivant Chea CH ae ‘C=C. Ne va H c= c=e cH, _NaINH.() (ta, LL a ger > CH. H oe ¢ ae “as 5 ca ait, H” cis H a A = ® ean 15. Answer (3) Hydroboration oxidation reaction Mechanism (Important point) = Syn addition => Product according to anti Markovnikov's rule. BoyTHF . ea Mecnanism pena —( D, a. ‘CH,COOH Syn-addition product 16. Answer (2) Oxidative cleavage of alkynes CHy ~C = C-H—aiingaa, ?CHs - COOH CO, CHCOOH— MH, CH, +1Na,CO, Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456Solutions (Parte!) Hydrocarbons 145 17. Answer (4) Elimination reaction OH i ic; CH,— CH CH CH, eacono HSOue a a (oy CH, ae Mechanism C. cH GH- CH CH, Oo ~ CH CH CH, eee H (hydride shifting) ch, CH, eer cra ou a cH oy a 3 s 18. Answer (4) cH, T chic -cl I A —ineea cH, \ (2) NaNH,(excess) Elmina cH) I cH—c =cH, (6, aH thereto it shows o == Conjugation (Hyper Conjugation) 19. Answer (2) Hi: OF + Br, —— Br 20. Answer (2) ° ° __H.pscaco, cy” (Oars Corporate Office : Aakash Tower, 8, Pusa Road, New Del }10005. Phone : 011-47623456446 Hydrocarbons Solutions (Parts!) at. 22. 23. 24, Answer (3) Nucleophilic addition reaction mesg = neon, a ae egal me ° ° Hexan-2,5-dione Answer (4) When electron releasing group and electron donating groups present in benzene ring then electrophile comes according to electron releasing group. OH OH COOH OOH HINO, No, Answer (4) Electrophilic aromatic substitution reaction cH, oO + OH, ACR neous oY O Mechanism CH,Cly + AIC —+CH,Cl+ AICIz =. O P(e)" Ko pamaaay Oo E or ites or ae -C-O—-OC Answer (1) CoH, —HetantataineKmOL_, (GH, ), CHCOOH + CO, CH,C| It means it is an example of oxidative Cleavage Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456Solutions (Parts!) Hydrocarbons 447 i (CH,),CH C =0 O=C—> (CH,,H-C=CH i | OH H Terminal alkyne give white ppt with Ammoniacal AgNOs. (Cty), CH-C=C-H= AgNO, —s(CH,), CH-C=TAg+ 1H, Wrtepe 25. Answer (2) Hydrolysis of magnesium carbide give propyne Mg,C, —#° 5CH,-C=CH a CH,—C=C—H —2MHC, CH —G— CH, (Y) I cl a cH,—C— cH, ————> CH,—C=CH I Propyme @ a pyme ( 26. Answer (1) CH.-OH CH, ALO, a Dehydration 27. Answer (1) 2, 2- dimethyl butane Structural Formula = }10005. Phone : 011-476234564148) Hydrocarbons 28. 29. 30. Solutions (Part-I) Answer (1) Br o + AgNO,(aq) ——> Oo + NO; Most stable due to aromaticity Br i 2) + AgNO.(aq) ——> A + NO; Antiaromatic Br » A+ vem — A Non aromatic Br + (4) + AgNO.(aq) ——> a Anti Aromatic ‘Answer (1) Oxidative ozonolysis a “ Mo, II c=cHcH, —Y2 2 —c—R+cH,—coo# i (2) H,0,, R “ Answer (3) R CH.—Cl (C)en-tonere 2no,(antyerous or Mechanism HCI+ ZnClp —>H" + ZnCl; 20: OH Ea 1 H—C—H+W—>H-G—H Electrophile Electrophilc substitution reaction ee .CH,-OH Nucleophilic substitution reaction CH-OH _ CHCl Corporate Office : Aakash Tower, 8, Pusa Road, New Del 10005. Phone : 011-47623456Solutions (Parts!) Hydrocarbons 449 31 32. 33. 34. Answer (1) G\ CH,—CH,— CH — CH= CH, “or” ace Gratin 1 Hr hydride shifting CN Yo CH, Electrophitic Oe i GH, omatic substitution Me CH, Et+CH, Answer (4) ° or D.M.F -> Dimethyl Formamide { HC -N a ) a D.M.S.O ~ Dimethyl Sulphoxide (CH, - $ - CH,) Both are polar aprotic solvents which is suitable solvent for Sx2 reaction. Answer (3) CH, - CH, > Ethylene glycol I | OH OH a H. intramolecular H Bonding H H H Gauche form is more stable conformation of ethylene glycol due to presence of intramolecular Hydrogen bonding, Answer (1) cH, CH, Sea Sa a cH, —> cH, © ies aS LN H cH, H Cis-1, 2-dimethyl cyclopropane Corporate Office : Aakash Tower, 8, Pusa Road, New Del }10005. Phone : 011-47623456450 Hydrocarbons Solutions (Parts!) 35. 36. 37. 38. 39, 40. Answer (2) or Conc H, SOJ4, Elimination [E! mechanism} Answer (2) ‘Compound Number of monochloro derivative Product (1) | CH,CH,CH,CH,CH,cH, > 3 (@)| GH=CH.= CH= CH=CH, 4 ch, 2.- methylpentane @ | CH-CH,-CH-CH,-cH, —> 4 I cH, 3 - methylpentane (@ |CH.-CH-CH-CH—> 2 a CH, CH, 2,3-dimethylbutane Answer (4) H,0 t i H=C=C0-H > — > ch, = cH on Ltomerisations ory Ho HgSO/H,SO, : a wd Answer (4) —NOz group is powerful deactivating group. Answer (1) se 2, y= ESCH major product ‘As we know that (Na ethoxide) C,H, -ONa is strong base here. Tertiary butyl bromide undergoes elimination reaction Answer (2) Lin liquid NHs reacts with But-2-yne gives trans-But-2-ene as a product. CH, H Lin liq NH, ™~, “ CH,-C=C-CH, —““> — o=c H cH, trans-but - 2 - ene Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456Solutions (Parts!) Hydrocarbons /154 41. 42. 43. 44, 45. 46. Answer (3) in H H. CH, | CH, cH.— C Nox, H H : cH, 2-methyl propane Answer (2) a C— CH, +CH,—CH— CHC | | hy. CH GH— CH,+c, —S> Cry cH, CH cH, e Tertiary butyl Isobutyl %A= = x 100= 35.71 chloride chloride 4 ) ®) 8 %B=7q * 100 = 64.20 minor maior ‘Answer (3) Electrophilic addition reaction = reactivity of electrophilic addition reaction depends upon stability of carbocation order towards reaction with HX is cH .CH, C=C > CH,—CH=CH—CH, > CH, = CH, CH,” Ncn, Answer (2) Anti addition reaction Br Ser Answer (1) a cl lie! () NaN excess). + H—c—C—-H —C=C—CH [consecutive eiminaton HHA ncaa ‘Answer (2) Most powerful electron releasing group increases the electron density in the benzene ring then more will be reactivity towards electrophilic substitution reaction. correct order towards bromination in aqueous solution is S-O-O-6 Phenol Anisole Toluene Benzene Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456452) Hydrocarbons 47. Answer (3) When electron withdrawing group increases, acidic strength also increases. — strength of EWG is NO2>F>Cl NOz—CHz— C= CH is the most acidic in nature 48. Answer (2) HI-+ Red P is very good reducing agent cH, cH, \ Hit Red p | cH—o-1 + 2, cH—c—# | | cH, CH Butane 49. Answer (2) ol CH, cH, CH, CH, Hy CH, Is al Sec le aces c—¢ =— cc + CH—Cx CH # Pas ad m ™~ Lo cH, cH, cHy cH, cH. oH 1 2 There are 3 possible monochlorides products chiral Contre 50. Answer (3) = Elimination reaction » CHs0-K* (Potassium methoxide) is strong base leads elimination cH, H CH. CH—CH,—cH, ——*_» “c=o~ i KOCH UN > Br H cH trans but - 2 —ene. 51. Answer (3) Electrophilic addition reaction cH, CH, b Ho HSO,ai ‘OH major product 52. Answer (2) Hydroboration — oxidation reaction = Product according to anti-Markovnikov's rule (1) Hy THE = CH, —CH=CH, —“5%""_. cH, cH, cH, OH CH CH= CH, LR Che ~ CH — CH, —O Solutions (Part-I) Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456Solutions (Part!) 53. 54, 58. 56. => Oxymercuration - Demercuration = Product according to Markovnikov's Rule OH ef I CH,— CH = cH, UH ACEES, oy cH — cH, (8) (2) NaBH OFF Answer (1) ‘Syn-hydroxylation 4.KMn0OH OF nal aTrL oa oF Answer (1) Electrophilic substitution reaction. Electrophile attack aecorting | to electron releasing group (-OH). OH Cone. HNO, Spetysonaiea No, a 4- oes ‘Answer (4) Pa " % ® 8 © => Oxidative cleavage of alkene in the presence of acidic KMnOs. ° 4 —2eHg ®) (A) (c) anowor(2) Hoffmann Elimination " Sc OH — methylidene cyclo hexane Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456 Hydrocarbons /153454) Hydrocarbons Solutions (Parts!) 87. 58. 59, 60. 61. ‘Answer (2) Those alkene which have more number of a-Hydrogen lower will be its heat of Hydrogenation CH CH, = c=c has 12-alpha hydrogen, therefore it has least heat of hydrogenation a Ss cH, CH, Answer (2) Diastereomers : Those compounds which have no mirror images of each other are called diastereomer. cH, OH cH Fn ae 7 Chiral centres Answer (3) Reductive ozonolysis =CH=C=C(CHy), —pallee > CH CHO + CO, + CHJCOCH, Answer (1) Those compound which have greater number of a-Hydrogen greater is hyper conjugation. Hence reactivity increases towards electrophilic substitution reaction Order of reactivity towards electrophilic aromatic substitution reaction is a: ort a. a 3-a 2-a 1-0 No-o Hydrogen Hydrogen Hydrogen Hydrogen Answer (3) cH, CH; O | 1 oi ‘Anyd. AICI, c—CH, +CH,—C— C — Cl ————> I | CH, cH, Mechanism Formation of electrophile ; : fs (CHa; —C— C+ AlCl, ———> (CH3, —c— c —Smmsement, Cy. E + co | a I a cH, Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456Solutions (Parts!) Hydrocarbons /155 CH, | c—CH, C oreo CJ by é , 1H, cH, 62. Answer (2) Higher is the number of Carbon atom greater will be its heat of combustion. 63. Answer (1) Higher is the negative heat of formation greater will be stability Heat of formation (K cal’mol) = -3.343 \~Y -2.405 \Yy/ ~1.362 aA = 0.280 64. Answer (4) The most stable conformation of cyclo hexane is the chair conformation => There is no angle or torsional strain in the chair form of cyclohexane. axial position equatorial positior => There are 6 equatorial and 6 axial hydrogen. 65. Answer (2) Wurtz reaction 4 oH, CH, H | ate CHC Br Sora CHa Cae o— cH, cH, H HCH, 66. Answer (4) cH, H CH, H cH, cH, 1 ot It 1 I CH—C— C—CH,+cl—> cH,—c— C— CH,Cl+ CHC — C—CH, ve ie | ee | HCH, HCH, cou Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456456 Hydrocarbons Solutions (Parts!) 67. 68, 69. 70. 1 Answer (1) (+ roe ae Or a Br rt Rocleophil reaction attack. ‘major product ‘Answer (1) When trans-But-2-ene reacts with cold dilute KMnOx give racemic mixture =2 Syn hydroxylation is possible OH OH oH, cH. cH, cH H — otal * : ns la Pee KMnO, vy ~ “ a a ee H Su Hieron or cH, cH Enantiomer pair or (4) Racemic mixture. ‘Answer (1) C=C—H c cr (Nant Cr oo (Op--00, anti addition reaction CH.—CH—C=c—cH, ENE S cH— CH UH a oa N H cH, (trans)pent -2-ene Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456Solutions (Parts!) Hydrocarbons /157 72. 73. 74, 75. 76. 77. Answer (2) cl COONa Gone HNO, Fee, ~Hs0, ae Conc HNO, Sa cya “concH.s0,” rec Aand B are position isomers. Answer (4) Ifalkene has greater number of « - Hydrogen minimum will be heat of hydrogenation. cH, cH, Nanni c=c thas minimum number cndalison > of heat of hydrogenation. ‘Answer (1) Those conformers which have intramolecular hydrogen bonding are the most stable conformers, H id Intramolecular H-Bonding, H ‘Answer (2) Gx Lou vtn, Lg > r—on, Answer (1) CH,-CH- cH, +c, > cH,- ~CH-CH,— cH, CH, 1-Chioro-2-methylpropane ‘Answer (3) => Electrophilic addition reaction = Product formed according to stable carbocation. Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456458 Hydrocarbons Solutions (Parts!) 78. 79, 80. x 1 C\— c= core — CN- tcc, Mechanism CD- c= 08-004 ae (Op o-oo, Benzylic Carbocation O~ GH — CH, ~ CH: -( Nucleophilic attack) at stable C’. x Answer (4) x CH, = CH, +X, 24H, -CH, k Mechanism CH, = CH, +X,———>_ CH, - CH, +X” 7 Halonium ion aw CH, = CH, +X ———> CH, - CH, T 6 i Answer (3) Malate Sa Kc 280 Br CH, ~Br—Moe"_5 TH, - MgBr —2° CH, -D+Mg a 8 - oD Clihv Nay ether CH,-D TE 2cH,— cl ESTEE CH, - CH, Dy reaction bb (oy ©) Answer (1) Consecutive elimination Br Br ! \ AlcKOHia H,C-CH,-CH, jana? CH:= C= CH, AleKOW!A CHy-CH—CH Nang CH-C=CH Br Br Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456Solutions (Parts!) Hydrocarbons /159 81 82. 83. Br I CH,-CH.- ai Nanna (CH,-C=CH Br Br 1 cH-c-cH, AHH oH cock c Br ‘Answer (1) H- CH, - CH, <—— H-C. <6 acidic hydrogen Answer (4) 1, 4 addition of HBr at R.T.P A+ teed, Corporate Office : Aakash Tower, 8, Pusa Road, New Del }10005. Phone : 011-47623456460 Hydrocarbons Solutions (Parts!) 84, Answer (2) CH,H Nt i oreo Hh, Onn -CH, i ¢ i ay Hydride Shifting CH, fs T He " (Olniaewans (Olstaccane : poe OF 85. Answer (1) Cyclopropane undergo hydrogenation due to high angular strain cH, +H, —> CH,-CH,-CH,-CH,-CH, cH, Corporate Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Phone : 011-47623456