Hydrocarbons (Alkane, Alkene and Alkyne) (TEXQSRSINE=T] ONLY ONE CORRECT ANSWER TE YP Y aypssecees Eta Lindlar"s Na/NH 3 A Baa R—-C=C—R A and B are geometrical isomers (R —CH==CH—R) of which type ? (a) 4 is trans, B is cis (b) A and B both are cis (c) A and B both are trans (a) A is cis, Bis trans . Which is most easily dchydrohalogenated ? a (a a) ©)-a att) (ja (@)1 (b) 0 : (lt (d) alll with same case i The relative stability of the compounds given below is in the order. CH; CH; CH, (CH, —C=C—CH, (ll) CH; —C=CH—CH, (iu) CH; CH=CH, (IV) CH, =CH, (a) 1> a> 1H > IV ()IV>IN>1>1 (c) I> >0>1V (ad) >1>1V>I 2 (Sams ATL, BA and Bare: OOOO °OXOOD) wo 4 ). (om CH; cH; NalOg CH, —C=CH—C—CH, ——*~* » Products KMn04 CH; The products are :Hydrocarbons (Alkane, Alkene and Aikyne) 131 li (a)CH;— C— OH'(CH,),C— COOH Il (b) CH, —C—CH, (CH;);C—COOH Il . (c)CH,— C— CH, (CH,),C—CHO (a) None is correct 6. The compound formed when 2-butene is treated with hot alkaline KMn0O, is : (a) Acetaldehyde {b) Acetic acid (c) CH,OH -CH,OH (a) CH; «CH, -CO-CH, 7. Relative stability among conjugated dienes (i), alkenes (ii), alkynes (iii) towards electrophilic addition reaction is in the order : (a) G)> Gli) > Gi) (b) @ > iii) > Gi) (©) Gii) > (i) > @) @) Gi) > Gil) > @ BD,/THF 8. Cr “Hoyo” Product A, A is CH CH; @ (Fon (b) Cr (©) Cox qd) Cr ‘OH ‘OH ‘D D 9. Arrange the following alkanols 1, 2 and 3 in order of their reactivity towards acid catalysed dehydration. ; OH (1)CH;—CH—CH,—CH, Q2)CH; —t—cn, —CH; dx, bn &x, OH (3) (CH,),CH. —ta— CH," — (@)1>2>3 2 (B)2>1%3 ()2>3>1 (d)3>2>1 10. An organic liquid (4), containing C, H and O with the boiling point 78°C and possessing a rather pleasant odour, or heating with concentrated H2SO, gives a gaseous product (B) with the empirical formula CH. (2) decolourises bromine water as well as alkaline KMnO, solution and takes up one mole of Hy (per mole of B) in the presence of finely divided nickel at high temperature. (4) and (B) are : ()C,H,OH,C>Hp _ (6) CHjOH,CpH, (©)C2HsOH,C,Hy (@) (CH; ),CHOH,C3H, Ih. ©) + Bn— A Awill have configuration: :132 GRB Advanced Problems in Organic Chemistry for JEE Br Br : @) cx ) CL {c) both true (d) none is true Br Br 12. CH,CHO+ HC=CD “2, p (major), Pis: . gp , ou (a) CH, CH—C=CH (b) CH, — CH—C=cD il {c) CH; —C—C=CD (d) None of these Br CH; . 13. ‘CHy IE KON 5 Product. The product can be : ” Clls i CH CHs @ Cou co) (Kou © @ Ch, 3 14. Consider the following reaction, CH . CH; CH; CH,CH; base \ . CH,;—C—CH,CH, > ee +, =C te CH, H ‘CH; 1 a) ay Which of the following base will give the best yield of the alkene II as the thajor product ? (a) CH;07 {b)C,H,O7 (©) (CH3)3CO” — (@) (C)Hs)3CO™ 15. IUPAC name of I is: (a) 4, 5-Dimethyioct-4-ene (b) 3, 4-Dimethyloct-5-ene (c) 4, 5-Dimethyloct-5-cne (d) None 16. CH;— CH Cl; CH SE FEH, Product (1) + Product (11) OH ‘What is not true regarding the products ? (@) Product-I and I] are position isomers, (b) Product-I.and II contains the same number of sp? and sp” carbon atoms (c) The yield of the product I and II is same . () Reaction obeys Sayizeft ruleHydrocarbons (Alkane, Alkene and Atkyne) 133 17. Which of the following is not true about geometrical isomers ? (a) They have different physical properties (b) The have different orientations in space (c) They have different connectivity of atoms or groups (d) They are non-interconvertible 18, 2-methy! propene is isomeric with But-l-ene. They can be distinguished by : (a) Baeyer’s reagent (b) Ammonical AgNO, (©) Br, solution : (d)O,,Zn/H,0 19, Which of the following is the structure of propylene chlorohydrin ? (CH, CH— CH, . (b) (Ha CH Cz f ca OH cl OH () CH; —F—CHs (a) CH, —CH—CH, OH HCl , 20: Which alkene on oxidation with acidic KMnO, gives only acetic acid ? (@) CH, =CH—CH, (b)CH,—CH=CH—CH, (6) Ethylene (a) Pentene - 2 . 21. Ethylene reacts with osmium tetroxide to form an osmic ester which on hydrolysis gives : : (a) Fthyl alcohol + Osmic acid (b) Glyoxal + Osmic acid (c) Ethylene glycol + H,0sO, . (d) Glycollic acid + H,OsO, 22. Diborane reacts with terminal alkenes to form trialkylboranes. These react with alkaline hydrogen peroxide to form : (a) Secondary alcohols (b) Tertiary alcohols (c) Isobutyl alcohol (a) Primary alcohols 23. Kharasch effect operates in which of the following ? - (a) CH\CH,CH=CH, + HCI (b) CH,;CH, —CH=CH, +HBr ' (c) CHy;CH=CH — CH, + HBr (a) CH\CH,CH==CH, + HI 24. A hydrocarbon X adds on one mole of hydrogen to gives another hydrocarbon and also decolourises bromine water. ¥ reacts with KMnO, in presence of acid to give two moles of the same carboxylic acid. The structure of X' is: (a)CH,CH—=CH-CH,CH,CH, - (b) CH,ClCH—=CHCH,CH, (c)€H,CH,CH —CH—=CHCH, © (@)CH, =CH—CH,CHCH, 28, Téentify Z in the sequence / fl CgHs07Nat CH,—CH,—CH=cH, 22, y SBP ™ 7 (@)CH;—CH— CH}, —0— CH CH CH, : ()CH, CH, —CH--O—CHj— CH cH,134 GRB Advanced Problems in Organic Chemistry for JEE ; (c) CH, — (CH, ), -O— CH )7—CHy CH) CH yO Ch 26. CH; —CH=CH, ——>—-» product X, Yis: H202/0H~ (@) CH, —CH— CHD . (0) CH; —CH—CH,OH OH D {c)CH s—FH— CH, (d) none is correct op CCl. 27. CH, =CH— CH=CH, ——*> product. The major product is : (a) Br—CH,—CH=CH—CH, —CCl, (b)CH; =CH—CH—CH,— CCl, Br (c)CH, =CH— CH CHy—Br CCl, (d) none is correct 28 ‘CHs (1) He{OAc)2/H20/THP . ‘@)NaBHg/NaOH/20 Ais: » OH ‘CH; CH; CH, CH; (a) C Son &) © @ cy OH 29. 2-Phenylpropene on acidic hydration gives : {a) 2-Phenyl-2-propanol () 2-Phenyl-1-propanol (©) 3-Phenyl-I-propanol (4) 1-Phenyl-2-propanol : 30. cis-2-Butene on reaction with Br, in CCl, produces mainly : {@) 1-bromo-2-butene (b) 2, 3-dibromobutane ©) meso-2, 3-dibromobutane (@) )2, 3-dibromobutane 31. Which of the following reaction will lead to the creation of two chiral centres in ‘the product ? Ig (a)CH,CH=CHCH, +Br, “45 (6) CH,CH)CH=CH, + Br, SO4> (©) CH;CH=CHCH, +HBr-——> | (@)CH,CH,CH=CH, + HBr —~> 32. The reaction of ethylene with Br, in water in the presence of NaCl gives : {@) 1, 2-dibromoethane (b) 2-bromoethanol (c) 1-bromo-2-chloroethane (d) all of theseHydrocarbons (Alkane, Alkene and Alkyne) 135 33. A hydrocarbon C,H, consumes only one mole of H, on catalytic hydrogenation. The hydrocarbon when heated with hot and concentrated alkaline KMnO, gives cyclohexanone and acetic acid (after acidification). The hydrocarbon is : (a) l-ethylcyclohexene (b) 1, 2-dimethylcyclohexene (©) ethylidenecyclohexane (4) eyclohexylethene 34. Dipole moment of which compound will be maximum ? HC oH Hy H H oH HOH @) = (b) \( © -@) = H cl H cH H cl H H (@) CH, =CH, >CH; —CH=CH, > (CH;),C=" (b) CH, =CH, > CH; —CH=CH, < (CH3),! i (c) CH) =CH, <(CH;),C=CH, ) Boa 2S Aand B are OS ay 0D HOOC COOH . © C) » ¢ ) (a) none is correct OHC CHO136 GRB Advanced Problems in Organic Chemistry for JEE 40. Index of unsaturation (H-deficiency) of CgHjq is ... and if it has a sixcmembered ring, it can be : (a4, C)-cmcu 4, (c= cH, ©4 ( \-ci,—an, (d) All correct 41. Which of the following yields But-2-ene on dehydration with conc. H,So4 ? (a) 2-Methyl-2-butanol (b) 2-Propanol ; (c) 2-Methyt-2-propanol (d) Secondary butyl alcohol 42. An alcohol (4) on dehydration gives (B), which on Ozonolysis gives acetone and __ formaldehyde. (B) decolourises alkaline KMnO, solution but (4) does not. (4) and (B) are respectively : (a) CH,CH,CH,CH,OH and CH,CH,CH=CH, (b) CH,CH, — cH —CH, and CH,—CH=CH—CH, - OH . (d) (CH, ),C—OH and (CH; ),C=CH,, (c)CH;—CH,— cH —CH, and (CH; ),C=CH, OH : 43. Which of the following compound undergoes dehydrochlorination most easily when treated with alcoholic KOH ? (a) Hy cH CH,CI ) CHa CH CoH cH; : a (c)CH, ~CH,—CH,Cl (d) (CH;);C—CI oO . ay a Which is most easily dehydrohalogenated ? @)I “ ®)H (Ml (d) all with same case 45. Cyclohexene on reaction with OsO, followed by reaction with NaHSO, gives : (a) cis-diol (b) trans-diol ’ - (©) epoxy (d) aleohol 46. Among the following incorrect statement (s) is/are : (a) In alkens the boiling point increases with a rise in molecular mass, (b) Branching in an alkane decreases the boiling point. (c) Boiling point of an odd numbered carbon atoms alkane is lower than both of its even numbered neighbours. (d) Melting point of an odd numbered carbon atoms alkane is lower than next even numbered neighbours.Hydrocarbons (Alkane, Alkene and Alkyne) 137 47. Ethylene reacts with Br, to give 1, 2-dibromocthane. The anti-addition takes place due to the formation of which intermediate ? hs . (a)CH,Br—CH, (b)CH,—CH, | (c) BKCH=CH* (d)CH;—CHBr NZ Na 7 Br Br 48. Which of the following reactions will result in the formation of a chiral centre in the product ? _ (a) CHyCH=CH, + HBr—> (b) CH, =CH, + HOBr—> 20; (©) CH,CH,CH=CH, +HBr —>» (4) CH,CH,CH=CH, + HBr—> 49. One mole of a hydrocarbon on ozonolysis yields one mole of glyoxal and two moles of formaldehyde. The hydrocarbon is : (a) CH) =C—C= CH, (b) CH) =CH—-CH=CH, CH, CH; (c) CH, =CH—CH,—CH=CH, (d)CH,;CH=C=CH, 50. A hydrocarbon (A) on chlorination gives (B), which on reacting with alcoholic KOH changes into another hydrocarbon (C). The latter decolorizes Baeyer’s reagent and on ozonolysis forms formaldehyde only (4) is : {a) Methane (b) Ethene (c) Ethane (d) Butane Alkane 1. The smallest alkane which can show optical isomerism possesses : (a) 5 carbon (b) 6 carbon (©) 7 carbon {d) 8 carbon 2. Which of the following alkanes has a meso stereoisomers? @ YY wry on oA 3. Among the following, the compound which has highest boiling point is : (a) 7S : (b) oy, @ ““~Y @ x 4, Propane can be best prepared by the reaction : Et20 (a) CH,CH,1+CH,I1+Na —22> 20. (b) CHyCH,COONa +CH,COONa ———.5 Electrolysis e 20 (©) CH,CH,Br + (CH), Cui 22, NaOH (@) CH,CH,CH,COONa > ; . Ps ;138 GRB Advanced Problems in Organic Chemistry for JEE w © 10. 11. 12. 13, (a) Me,CD on heating? (b) Me,COD (a) CH,CH,COOH 0 ll ° {| (c) CH; —C—CH,—C—OH Na . a_O-aG Product, find the product : fa) Cl —Cl © ~OO- a auth Product : Br @ BRAY MgBr (c) CH;—CH=CH), » Me ;CMgCl on reaction with DO produces : (©) (CD3);CD_— d) (CD3);COD . Which of the following carboxylic acids undergoes decarboxylation most easily ° (b) CH, —C—-COOH i @) (O)-0H ¢) BM. MeBr @ ZN |. Which of the following alkyl bromides may be used for the synthesis of 2, 3-dimethyl butane by Wurtz reaction? (a) AB (©) Isobuty! bromide Which of the following methods of alkane synthesis involves the electrochemical oxidation of alkanoate ion? (@) Kolbe’s method {c) Frankland method The reactivity of alkyl halides for Wurtz. reaction is : {a) 1°>2°>3° — (b) 32> 2°> 1° Which of the following is planar and cannot form conformational isomer? @) (OA Br wA (d) s-butyl bromide (b) Wurtz method (d) Corey-House method (c) 2°>3°>1° (d) 19> 3°>2° of] @ CO Which of the folowing reactions has zero activation energy? (@) CH,+CI° — Cn; +HCI ) cr—cl 5 2cr2 Hydrocarbons (Alkane, Alkene and Alkyne) 139 (c) CH} + °CH; —> CH,--CH, (d) CHS +Cl—cl —> CH,—cl+cl" 14. Photochemical fluorination is explosive while iodination is too slow to occur. The reason for this is : (a) bond dissociation energy of /, is minimum. () formation of CH; —F is most exothermic. (©) formation of H—F is most exothermic while formation of HI is endothermic. (d) F, has lower bond dissociation energy than Cl, and Br). 15. Which statement is incorrect about free radical halogenation of alkanes? {a) The number of product molecules formed by one photon is very high (b) If, is added, initially the rate of reaction decreases, then it increases (c) Inhibitors combine with free radical and terminate the chain reaction (d) Presence ofPh—G—0--0—F Ph inhibit the free radical reaction. oO O° : 16. Which of the following is not the chain propagation step in the chlorination of alkane? (a) R* +S80,Cl, —> (b) *SO,Cl —> SO, +CI" () Cl’ +R—H —> (@) R—O—O—R +2R—H —> 2ROH+2R" 17. An alkane cannot be chlorinated by using which of the following reagents? (a) Cl,/hv (b) HCI (©) SO,Cl, (@) t-Bu—O—CI 18. The correct order of heat of combustion of the following hydrocarbon is : Pent-1-ene Pentane neopentane isopentane @”) @ () 3) (a) P>O>R>S (b) Q>S>R>P () P>Q>S>R @) S>R>Q>P 19. Formation of free radical takes place with absorption of minimum energy in the formation of : Br Or Os © x @ +» 20. Formation of free radical is easiest in : @ “Aa ) Sp, © F @”~, 21. The correct order of relative density of following alkanes is : DW DAR AAW WS (P) @ ® © (a) P>S>Q>R (b+) R>S>Q>P () R>Q>S>P @) S>R>Q>P: 140 GRB Advanced Problems in Organic Chemistry for JEE 22. What is the chief product obtained when n-butane’ is treated with Br, in the presence of light at 130°C? : ay 0) Yer & bo @ “sr Br 23. The number of possible enantiomeric pairs that can be produced during monochlorination of 2-methyl butane is (a) 3 (b) 4 (c) 2 @i 24. For the given reaction how many products will obtain (all isomers)? KK 22, Products @1 (b) 6 @4 @ 3 25. How many total products will be obtained by monochlorination of 2-methyl butane and how many can be separated by fractional distillation? (@) 6,4 {b) 5,4 (c) 6,2 {d) 4,2 How many monobrominated products will be obtained by above reaction? (@) 6 (b) 4 { ©5 (d) 3 cH, : HD _ Brhy 27. HC-+-H Prodixcts : CoHs boy CH; CH; @ Hr? @ D (©) Both (a) and (b) (d) None of these H3C Br Br ‘CH . CoHs C.Hs CH, RyQ2 - 28. we—e—# +CCly Ty > Produet = . 7 y CH; CH; | (a) an cl (b) CHCl, ‘CH, . (©) Both (a) and (b) (a) None of theseHydrocarbons (Alkane, Alkene and Alkyne) 141 Hc. 2 cu, Br, by, 29. “> Product : WOH CH; ore | (a) Hyco CH,Br (b) CH, — CH; H Br. @ A* @ XK 30. How many alkane of molecular weight 100 are chiral? fa) 1 (b) 2 ©3 4 31, Which one is the correct energy profile for CI” +CI” —> Cl,? Energy Energy (b) Reaction co-ordinate Reaction co-ordinate Energy (©) (d) All of these Reaction co-ordinate 32. Which of the following is the correct statement regarding relative acidic character of cyclopropane and propane? : (@) Cyclopropane is more acidic than propane (b) Propane is more acidic-than cyclopropane (¢) Both are equally acidic (d) Both are neutral Fi iL 33. Ph—-CH—CH,—CH, 2s Products 2%", Fractions, iv Distillation . CH, ‘No. of products and no. of fractions are respectively : (a) 6,5 (b) 6,4 (©) 5,4, (d) 6,3142 GRB Advanced Problems in Organic Chemistry for JEE 34. Which of the following cycloalkanes has lowest heat of combustion per —CH,— group per mole? a7 ) oo © © @ C 35. Which of the following alky! halides is not suitable for Corey-House synthesis of alkanes? @ CHI OA OAN OX iT Br 36. The relative reactivity of 1°H, 2°H and 3°H in bromination reaction has been found to be 1 : 82 : 1600 respectively. In the reaction, y a» +Bry -, Xet Ape (4) (@) The percentage yield of (4) and (B) are expected to be : (2) 99.4%, 0.6% {b) 50%, 50% (©) 0.6%, 99.4% (d) 80%, 20% 37. The relative reactivity of 1°, 2° and 3° hydrogens in chlorination reaction has been found to be 1 : 3.8 : 5. In the reaction, Mae hay Ey cl ) ®) © (P) The ratio of the amount of the product (4), (2), (C) and (D) is expected to be : (a) 1:3.8:5:1 (b) 3:7.6:5:6 (c) 3:7.6:5:3 . (d) 1:7.6:5:1 38. Which of the following is the free radical chain reaction? (a) 2CH3I+2Na ——» CH,—CH, +2Nal (6) CH, +Cl, > CH,CI+HCI ee (©) 2CH,COONa —*> CH;—CH, +2CO, +2NaOH+H, (@) All of the above 3. Ll» +HBr — Product : . Br @ A oA © A oA Br Br .Hydrocarbons (Alkane, Alkene and Alkyne) 143 40. ~V RCN, 20s—Ak05, Major product : @) CO o) “AF OAV @) Co 4b, AWA 220 hs, . ) Mi ew My © Ay @ wedy 43. Bear, SARE Product : > OA o) oZX @ wC=c=cH, 4. The bond dissociation énergy of the C—H bond for the compound Hy\C—H HyC—CH,—H nc~cr—cr,—a Van (P) (R decrbades in the ordel ® “ (a) P>Q>R>S (b) S>R>Q>P (c) S>P>Q>Rk (d) Q>P>S>R 45. Which of the following carboxylic acids is difficult to decarboxylate? - @) J, 0) “or ©) ae @ ony mn 46. The method of estimation of active hydrogen ii in a compound by reaction with L. CHMgl is known as : (a) Zerewitinoff method (b) Hinsberg method (c) Zeisel method (d) Victor Meyer's method144 GRB Advanced Problems in Organic Chemistry for JEE SH Hs“ Hy/Ni 47. S=0 9 ‘The end products of the reactions are : (@ SH and \gy (b) >—S—CH;—CH;—SH sa SH © x and H,0 @> and ig’ 48, Consider the following reaction : PhyC—O—O—CPhy + CCly ——§£_—> A - The major products formed in this reaction are : @ XX. and CHC; (by x and CHCl cl on 1H ~ ) Hand x (@) No reaction ' 49, Ar , Find out number of monochlorinated products (including stereoisomers) which ‘are possible in the above reaction : (a) 2 (b) 3 @4 (@) 5 (CH, 50. Ch, Hy, Pd . 3 Products of the above reaction will be : (a) racemic mixture (b) diastereomers (c) meso (d) structural isomer D NHz—NH; 5h. Cr MEE, Product 30 D femit (@) Both (6) and (e)- D CH; Hy Hy @) @) 2 © Hy Hy HC CMe; - CMe; CMe; “nyHydrocarbons (Alkane, Alkene and Alkyne) 145 53. On catalytic reduction with H,/Pt how many alkenes will give n-butane? @ 1 (b) 2 ©3 (d) 4 H. D sa, ‘= <, Hy/Ni 3 Product of above reaction will be : (a) racemic mixture , _ (b) diastereomers. (c) meso (d) constitutional isomers Hy CH; - 55. “ed ARN, D Product of above reaction will be : (a) racemic mixture (b) diastereomers (c) meso (d) constitutional isomers Pram (mete P : @ cy @) Ci © ag (d) None of these 57. FROM, Product: @ cr b), CL © Cr (d) None of these Br—Hy Hy —Br NA NYE, Major product : Cc. Br Ncrt—Br ‘ Br ‘Br “OC ob Br: ‘Br : Br. Br © XX @ \ a . . Br Br Br 59. Arrange the following alkanes in decreasing order of their heat of combustion : - Hs cat—cH, YN YN CH, w wr) @) (a X>Y¥>Z (BR) Z>X>¥ ()Z>¥>X =) X>Z>¥ 58.146 GRB Advanced Problems in Organic Chemistry for JEE Alkene and Alkyne 60. Which of the following is the major product when 1-butanol is heated with concentrated H,SO,? (a) 1-butene (b) Cis-2-butene + @) Trans-2-butene (G) All of these Hi 61. Cone. HPO OH - Ht @) Ay () © ys @ »y , ° 62. In the reaction e CoH0' Vby ©:H;08 The major product obtained is : (a) Ay ©) HY Hs (©) A “ @ NG . . “on . * 63, sk one Ha804, Major product : =< & Xv © SK © None of thesé 64. [ )—cu—on SE HPOL, Major product : , wDeo of oof 65. The major product of the following reaction is : . BLA Jer Na/Ether Br, hv Alc. KOH : oC) ot ott @ Cr jHydrocarbons (Alkane, Alkene and Alkyne) 147 (c) Both (a) and (b) COOH KOH 67. CH; —CH— CH— CH, ——_> Product : ” I Electrolysis. COOH coo°K® coo°K® @ Neots of oh ol co0°Na® | . @. Electrolysis, wajoe : ‘COO*Na® | oD cS “Oe © . (dd) | ou CH3 CH3 OOOO et erin (a) LiAIH, (b) Hy/Ni (©) NaBH, (d) H;, Pd —BaSO, 0°kK® ; . : 70. Electrolysis, Product : toa exe . ~ Ou 0 @) () CoD (@) None of these148 | 71. Th. 73. 74, 7. GAB Advanced Problems in Organic Chemistry for JEE nn Which reagent will be used for the above conversion? (@) Na/Lig. NH; (b) H,, Pd—CaCO, (©) Li, Ph—NH, @) Hy, Pt H . Li Lig NH, Major product : HH . HH La) HOH @ Jd ® dj © cy @ js 3 Beta NH, Major product : Hy Is Hy (a) ) @ (@) None of these Which of the following has zero dipole moment? CHC CH CHC, J" @ JS ©) HW. ONH Ww Noh CH, Is CHs. H ©: a a“ @ ad Ay Non Which of the following is correct order of stability of alkene? (2) CHy—CH=CHy < \=/ < eX < SS : (6) CHy—CH=Ciy < N= <\, < DC a © KX <<’ < CH CH=CH, (@ \=/ < CHy—CH=CH, < =X < aNHydrocarbons (Alkane, Alkene and Alkyne) : 149 716. Which of the following alkenes is most reactive towards electrophilic addition reaction? {a) H,C=CH, (b) CH; —CH=CH, HG. © =CH; @ H,C=cH—Cl Hy 77. Propene reacts with Br, to give 1, 2-dibromopropane. The anti-addition takes place duc to the formation of intermediate : Br | . & (@) CH, —CH—CH, (b) HyC—CH—CH2 . N\BZ Bi “ @ S (©) H;C—CH—CH,—Br ° — @) Noneof these 78. Consider the following reaction : cH, He—F— CH=CH + HCl —> CH; . ! The major product obtained in the reaction is : cl CH; CH; Cl ~ : rd , @) Hee CH—CH, () Bice CH—CH, ' CH, cH, CH, ; © ney owen (@) None of these CH 79, Which of the following reactions is expected to give a fairly ood yield of » (CHy);6-—CH=CH,? : 30H . oe (a) H;C—E-—CH-CH, (b) sc H—CH, 5 | 2804 : cH; 20, setone_ 150 GRB Advanced Problems in Organic Chemistry for JEE CH: IC] ACH . a H3Br © oe (a) He ptt, e > fina CH3 Me,CO 80. on—\—crcu—c, 89, Major product : cl Ci. @ on) —bion, @) ont) bcm —ony © on) circu, (@ None of these 81. wc—o¢ \—camcr—ony EBS, Major product : ir @ nico (cr. Laon ir neohome ©) Both (a) and (b) in same amount ‘@ None of the above 82. HyC=CH—C=CH + HCl —o X;'X" is: a . | @) HYC—CH—C=CH e) HsC=CH—F— CH : cl a a lL: | (©) CH, —CH—CSCH @ CH, —CH—F=CH, re! 83. Arrange the following reactions in decreasing order of electrophilic addition reaction: CH, CH, CH. veer, 2 . aH, ae cay on, —6F cCHy— ) @ CC) @) P>O>R @O>R>P =) R>Q>P (@) P=Q=R 4. Hydrocarbons (Alkane, Alkene and Alkyne) 181 84, AZ BE Mele) , Major product : Br ° ir @) No () a © C4 (d) None of these 85. The reactivity of alkene Hs Cy H;C—CH=CH, ° poh HC—¢ CH=CH H3C ony : (x) vy (2) towards hydrogen is : (@-X>Y>Z° )Y>X>Z © Z>X>¥ WG Y>Z>X CH; ‘ 86. HyC—CHC—C_ 1 EP B88, product :” : Ww Isoquinoline HO “CH, (a) an optically active compound (b) an optically inactive compound (c) aracemic mixture (d) a diastereomeric mixture 87.2 Cy Cone. Hy80s, ,_PUHa, » A and B respectively are : OOOO OOO) BH; .THF Hg(Ac);, H20 ae CH H202/OH NaBH, OH 88. B A A and B are respectively : Hs (a) CX both 0) (cou both 1H . © CX, and ( )-cri08 (a) ( )-cr,o1 and CX, H ” at152 GRB Advanced Problems in Organic Chemistry for JEE 89. What reagent is needed to accomplish the following synthesis? CH; Hy. CH HAG yal -> oy Na Hon H . e @ HIO (b) KMn0,,0H = (c) 03, Zn/H,0 (d) Ph—CO,H 90. Which compound will yield 5-keto-2-methy! hexanal upon treatment withO3? 3 Hs Hy Hs : Hy : Hy @ &) () {d) Hy CHy Ht . 91. on OL, Major product : ” Cemex emis, 2 B950+ , Major product : Peroxide, 93. HyC—CH=CH, + HCl —"*s Product, the intermediate of reaction is : (@) CH,CH—CH, (6) CH —CH,—CH, (© CH,—CH—CH, . .@ CH, —cH,—CH, (CHBr; + Alc. KOH 94. (ES jor product : iT jr Br Br ) xX ) oO ox deo Oo ir Br BrHydrocarbons (Alkane, Alkene and Alkyne) 153 CHCh+Al.KOH 9. {| Y}_CHCh + Ale KOH, ior product N | H 1 1 of, wt. oS ot (a) ( a Oe w WAG HyCH; | 96. NBS, y Ale. KOH, Hg (OAe)p Ph-CHOH 2; NaBHs, OH \CH,—Ph CH, H—CH; @ o ® ly —CH;,—O—CHz— Ph ‘H==CH) © o © CHj—Ph Hg, Ni . 97. o Mele” Product : ° O © o 6 S «a nova 98. Fastest rate of electrophilic addition takes place in : @) wil \-¢ \ cuore () on \-¢_\-crmey154 GRB Advanced Problems in Organic Chemistry for JEE © HC CH=CH : @ CH==CH, < 99. Which of the following will be the correct product of reaction? Cone. H3PO4 mei a fa) p OH © a OH ory 100. Give the reagent that would best accomplish the following reaction : H s O-OE" “Ny “OH (a) Cold KMn0, (b) CF,CO;H, H®/H,0 J (©)'0;, Zn—H,0 (d) KMnO,, 4, OH 101. Arrange the following ajkenes in increasing order of their enthalpy of hydrogenation (— AH) : Gercsomor (@) R (b) —_ ea NaBH, OH , BH. THF BH. THF > So © O 10>, NaOH @ oO #0, NaOH 104, Give the major product of the following reaction mut CN dwt . ir HAC Ph , 108. =< ee, ' H H : Ph . Ph it 1 H-+-Cl @ a4 . © utc CH3 CHy Ph H--Cl (©) Ph—C=C—CH3 @ H--CCh . CHy 106. Give the major product of following reaction156 GRB Advanced Problems in Organic Chemisty for YEE" + 107. Which of the following products is not formed in following reaction? Ve Hg (OAc), H20 ——o > Major luct : 08. ry NaBD,, OH ior pros (@) “ (b) Cho © Ce. @ Oe * , Hg (OAc), CHOH Pci Hehe SOK ‘Major product : one NaBHy, OH 3 ee Ph, 1H—CH, @ ) = cH’ ‘on cH’ “iy Soe (©) (d) None of these ‘cay Yocny cH. \ Hg (OAc), D,O . . 110, PaO app, OH Major product D CHy * : CH: Hy—D CH: 5 CHS ‘OH CHY ‘oH CH: Hy—D , CH fa © @ cay Sp cay Sop Phy S=ct EEO Major product : ” cy Ph. 1H Ph Ct ® SC oOo x CHs Nout CHy H;—OHHydrocarbons (Alkane, Alkene and Aikyne) 157 - Ph. Hy—Cl Ph Hyz—OH (d) CH: is cen Bs Major product : ny, H,0,/0H HH Ph. CH.—-CHs Ph CH, ) x ®) x cH, cH” ‘ou cHY y iy . 1H mda oS tycn, \ owen © CHS D 113, Which of the following reagents will bring about volowig transformations? HQ, u (a) C1,/H,0 (b) PBr;/H® 3 8 (©) Hg(OAc);, H,0/NaBH,,OH (4) BH .THF, H,0,/0H 114. Which molecule will give following dicarboxylic acid upon treatment with acidic solution of KMn0,? 0 for fonts 115. Which of the following reagents would best accomplish the following transformations? Bk 2, Ay158 GRB Advanced Probiems in Organic Chemistry for JEE (a) Excess B,H,;NaOH/H,0, followed by 0sO, e . (b) Excess Hg(OAc);/H,0; NaBH,, OH followed by cone. HjSO,, A 9 (©) 03, Zn/H,0 followed by Hg(OAc), /H,0; NaBH, OH (d) 0s0,; NaHSO, followed by NaOH 116. What is the product of the following sequence of reaction? '=CH NaNH,/NHy, H,Pd-BaSO, BH. THF eee = H,0/0H “ORES GIS 117. Which would produce chiral molecule after treatment with Lindlar catalyst? oF ow (s ok= = 118. Which of the following compounds was starting material for the oxidation shown below? Compouna MOO, a +00. 119. How is the following transformation best carried out? i (a) 0s0,; NaHSO, (b) H)S0,/H,0 (©) HeS0,/H,S0, (@) HIO,Hydrocarbons (Alkane, Alkene and Alkyne) 159 120. The product of following reaction can be best described as : HBr (a) a racemic mixture (b) a single enantiomer (c) a pair of diastereomers (d) an achiral molecule ta, AZ SBS, x HE y BS, 7, zis: HyO2, A H3 @ lL] ) XK on @ OQ 122. Product of following reaction can be best described as : BryCCl fCCly s s rc (a) meso product (b) a pair of enantiomers (c) structural isomer (d) a pair of diastereomers 123. Which of the following reactions results in the formation of a pair of diastereomers? HG, a Hy a (a) oy BS ) a ae 1G, a HG, Ht _ HBr SZ BH. — aS © SY 705, bv @ . w0nbH ww AAs, BaCS2, Major product : @ (Xe © w An, 0 p Ann, @ ~O y CH: 125, OX —HBS, Major product : OK, Ose OCBa OCT . Br Br Br Br160 GRB Advanced Problems in Organic Chemistry for JEE 126. JS HB, Major product: rr Br : Br 127. Ha MOle) Product : PRO, “SD 0 Q 6 g “ QO =O & CH3 Stereochemistry of the product are : (a) diastereomers . (b) meso (c) racemic mixture (@) pure enantiomersHydrocarbons (Alkane, Alkene'and Alkyne) : 161 Cy 2NaNH2 |. Ha, Pd-CaCO3 130. Ph—CH=CH— Ph ca X ——> YZ aN product (Z) of the re reaction. ve vo {a) =C ws a =< » Smart (4) Ph—C=C—Ph Pi KX Eres CREO, ne MOE ioe —7CPBA(] Mole) HX oC oh, a 133. wie Watico;” ” ; i H3 134. Or Oe, NaHSO, Hs162 . GRB Advanced Probiems in Organic Chemistry for JEE 135. Which of the following is major product of reaction shown below? CBs © oh 136. A triene treated with ozone followed by CH; —S—~CH; to give following three products. What is the structure of triene? 9 0 Product = waa moe DA, HO 9% 6D oO 137. If the following compound is treated with Pd/C in excess of H, gas, how many stereoisomers of the product will be obtained? @ 1 * (b) 2 (3 @4 CH; CH, . 8° (ee | Product : “pb CH; CH, ff @pre mere of FB @ Altofthese CH, CH; CH; Hs 139. Bade . #;02°0H CH, CH; H H H o bf o@l, oGh oe . OH \__/OH D OHHydrocarbons (Alkane, Alkene and Alkyne) 163 140. An organic compound C,H, on reductive ozonolysis gives HCHO, CO, and CH,CHO. Find structure of compound. (a) HyC=CH—CH=CH, (b) CH; -CH=C=CH, © La . . @ HyxC—C=2C—CH, HCHO, H® 141. CY Ho” Major product : ro) a ) he © CT, @ ag today hry ay Reagents (A) and (B) in above reaction : {a) CF,CO3H, H,0; (b) CF,CO3H, HIO, (c) CF,CO3H; 03, MeS (d) All of the above 143. Which reaction will occur at the fastest rate? HH 1. Hg (Ac) RHE OAD 464 : mS > wap,®OH Major product H HH 0 @® ) O ©) a) OQ f HBr 145. Se “ey » Comment on optical nature of product.164 * GRB Advanced Problems in Organic Chemistry for JEE {a) Racemic mixture (b) Enantiomer (©) Diastereomer (d) Optically inactive ° 146. Arrange the following compounds in decreasing order of rate of electrophilic addition reaction. i =CHy o ‘CH eo ‘CH, 3 ‘H==CH) CH; H ve ve o @ ® (2) Q>S>P>R (b) S>O>R>P (c) P>O>R>S (@) R>Q>S>P Identify products Y and Z. Hs CH; So So oF @ and SS ©) SS and Ow H ‘0 0 : H . CH; : H : ~ (© Both are {0 (@) Both are wo So SS H ‘0 m-CPBA wall] CO “a product : . HHHydrocarbons (Alkane, Alkene and Alkyne) HI (excess) 1 19. 0A oa I I (a) MM wA © aw : @ mw T 150, What is the final product of the following reaction? . oO @ Jay 0) MS oO © H @ epg" ‘ i 151. Which of the following is not formed in given reaction? NBS CCl,” HS 9 9 wt 152, Which of the following is major product? _HCL(I Mole) “Tow Temperature” Temperate Ci Cf wr Qa « 153. Select the reagent for following transformation : +-c=ci—— a (a) Hj-Pd, HCHO, H,SO0, (b) Hy, Pd-BaSO,; Hg(OAc)2, H,0, NaBH,, OH ° (©) BH3, H,02, OH, Pd-C (d) Hg*?, H,S0,, H2, Pd-BaSO,166 : GRB Advanced Problems in Organic Chemistry for JEE 154. Select the starting material for following reaction : i He (OAc), 140 , : . ~ NaBH ‘OH (a) ot () (a) Both (a) and (b) 155, Select the best starting material ‘or the following reaction : , : a § H 9 On 20-0 Bch cB cy 156. Choose the best reagent to carry out the following transformations : 3 te H OH (a) Lindlar catalyst; NaNH,/NH; (), 1-bromopropane (b) NaNH,/NH, (), 1-bromopropane; Lindlar catalyst (©) NaNH,/NH, (0), 1-bromopropane; Li/NH3 (J) (d) Alll of the above . 57. Which of the following will be most reactive in the addition reaction with HBr? (a) CH;—C==C—CH, . ) As ) O @ SIT. 158. Consider the ee rearrangement reaction. eae mk on Hj;C—C:Hydrocarbons (Alkane, Alkene and Alkyne) 167 | Which of the following reaction co-ordinates best represents overall reaction? wh ® | Wn Reaction co-ordinate Reaction co-ordinate . | © | @ Reaction co-ordinate Renoton co-ordinate 159. Compound (¥) 22729, YC Ww Find the structure of (X). @) 1S (b) oT (©) wy @ cr < CH)—CH,—Cl (a) (b) 1 rg {c) : (@ 0. \—cu=cr{_) BBY, Major product: . PY @) m—pcon{ ) &) mr—cHy—cH{ , : © Coane) (4) Both (a) and (b) ‘Br . .168 GRB Advanced Problems in Organic Chemistry for JEE 162. The product of following reaction can be : Agi @ <~ am) \H © Oy @ << h CHyHydrocarbons (Alkane, Alkene and Alkyne) 169 CHB, Me;CO"K® @ ©) oe rc Br Br ‘Br* om ce Bry + HO 166. ——s pH Product : B21 th » Product : ts CH, CHy Hs oFEE Ss oa © MEER o MERE CHy CH; H 168, Rates of hydration of the following alkenes are : CH;—O—CH=CH, F—CH=CH, CH,;—CH—CH, @) (@) ®) &S-cn=cr, 3) (a) P>Q>R>S . (bt) S>R>Q>P (©) P>S>R>Q ‘ (d) R>S>P>Q 169, Rates of hydrohalogenation of the following alkenes are : (\-ci-on¢_ cu—cn=cr/_) @) @) CH;—C—CH=CH, “Cy —CH=CH—CH, Hs aR) S) (@) P>Q>R>S (bt) O>P>R>S (©) O>P>S>R - @ P>Q>S>R170 GRB Advanced Problems in Organic Chemistry for JEE 170. Rates of addition of Cl, /H,0 of the following alkenes aré : 9° CH CH,=CH, CH,=CH—C—H CH,—CH,—CH—CH, CH;—C=CH, (P) @) 4 () (S) (a) S>R>P>Q ‘ (bt) S>P>Q>R (c) P>Q>R>S (@) P>Q>S>R Red hot i. 3CH,—_C=CH ———> “Gib.” tube Hs Hy o( 00 © a oC HC ~ CHs NaNH2/NH3(!) CH3CH2Br Li, NH3() 172.CH,CH,C=CH 2, SO, HO @ aa (b) CH,CH,CH=CH, Sa CH3CHa, PERCH (©) Pay @ =a ‘CH)CH3 H H 173.CHCH,CH, —C—H+CH,—ca=cu N& NH, : OH . iC . C. @) wh ‘cH; © On, 1H Cc. © (YF en @ ~~ OH HT 174, The products of the following I and II sequences are related as : (a) diastereomers (b) identical (c) enantiomers : (4) geometrical isomers CoyHydrocarbons (Alkane, Alkene and Alkyne) m1 =CH Brz, H20 175. —e Br Br C=CH c=c™ {Nea (a) (b) Br Br Br C=CH ©) @ Yor KNH) Hy “Br/CCly KNH) 176, HC=CH ——_—_——> 4 ——_-» 8 > C —_> D Ci—(CH2},—Cl Pa-CaCO3. * (Mole) Na, NH3(/) —— E; Eis: “CO CO {c) Ca (d) None of these 177. Which is the most suitable reagent among the following to distinguish compound (3) from rest of the compound? 1.CH,;—C=C—CH, 2. CH; —CH,—CH, —CH 3.CHjCH, —C==CH 4,CH;—CH=CH) | >. @) Br; inCCl, (b) Br, in CH;COOH (c) Alk.KMnO, (d) AgNO3/NH,OH 178. Two gases P and Q both decotourise aqueous bromine but only one of them gives white ppt with Tollen’s reagent. P and Q are likely to be : (a) H,C=CH, and CH;—C==sC—CH, (b) HC==CH and CH;—CH,—C=:CH (©) HC=CH and CH;—C=CH : (d) CHj;—CH,—C==CH and CH; —C==C—CH, [-472 GRB Advanced Problems in Organic Chemistry for JEE _BH THE 179. Sy aes 7008 @) ©) © @ WY Asa “~ ( H 180. Which of the following hydrocarbons should be choosen as a starting material to prepare 3-hexanone by the hydration? @) AFH 6) ANS : L, m AO @AFVY Br Za, dust, oust et ea Bi Br x Bi yo (a) c=, (b) Jo “) H-—C=C—H (d) CH;—CH HBr oH” Nee 182. Among the following compounds which one cannot decolourise alkaline | KMn0O, solution? (@) HC=CH (b) CH; —CH, —OH oO (c) CH; —C—H (® CH;—CH, '=CH NaNH Dz mr | pm 74 Pemaso? 8 _End prodhict B is: €D=CD, Ph D Y \ 4 (a) 0) C=C vw OM PR © c=c (d) Ph—C=CD vb “pd Phat a 184. C= 2 Py Nr The major product is : Ph H a) Yo=c (b) Ph—C==C—Ph PK” SNH (©) Ph—C=CH (d) None of theseHydrocarbons (Alkane, Alkene and Alkyne) : 173 (Sia)2, BH P 185. Ph——C ==CH- P and Q are respectively : ° ° ll (@) Ph—C—CH, and Ph—CH, —C—H ° (b) Ph—CH,—-CHO and Ph—C—CH, ° ° Ul Il (c) Ph—C—CH, and Ph—C—CH, (@) Ph—CH,—CHO and PhCH —CHO BH3. 186.CH, —C=C—CH, _BHSTHE Major product : CH3COOH Il (a) CH;—CH,—C—CH; (b) CH;CH;CH; oH . . , CH. CH yi Ky _ Cis © c=C @O Yn nce H 4 187. Which of the following molecules is not linear? (a) 0 (b) H.C: © HC=C—C=CH _ @) HC=cH 188. Which of the following reagents can be distinguish propyne from properie? (@) Br), CCl, (b) Dilute KMnO, (©) Conc. H,S0, (@ AgNO, in NH,OH 189, Which alkyne gives 3-ethylbexane on catalytic hydrogenation? S S @ (by Il (c) os (d) Allof these 190, Which rection yields the major product shown? HH 1,0 Be"? 120 @ >= sno? () >= ino, Bi ir © > = Vk @ >= ae? : ct if174 . GRB Advanced Problems in Organic Chemistry for JEE 191, Ph—-C=C—H 2. Major product : Cys I I (@) Ph—C=CHHI (b) Ph—CH—CH, —I (©) Ph—C=C—I @ I-c=c—H ‘ si =C—CHy 92, — To carry out above conversion which reagent will be used? (@) CHBr,/NaOH,Na/NH,()) _—_(b) Na/NH,(), CHBr,/NaOH (©) Hy/Pd-BaSO,,CHBr;/NaOH (4) H,/Pd-CaCO, CHC), /KOH 193, ( aon + CHCl“, Major product : H cl @ (b) ‘CHCh, ‘CH,CH,CI cl 1 a 194, (O)-cr=cr—no, Bes 1-24, Major product: (a) Ph—CH,—CH,—NO, (6) Ph—CH,—CH,—NH, (c) Ph—CH,—CH,—-NH—OH — (d) (cc —No, “ H,0/H,SO, 195.CH,-—CH,—O—CH=CH, —————> The product/s formed in the reaction is/are : (@) CH, —CH, —O—CH,—CH, OH on | (b) CH; —CH, -O—CH— CH, (©) CH,—CH,—OH and HO—CH—CH, oO tl (@ CHCH,—OH and CH;,—C—HHydrocarbons (Alkane, Alkene and Alkyne) 175 mC es EL O YH oO of 0 0D OH mn VY -L.NAHCOs, Major product : T T I . OCOONa (&) (rood Na’ @ (roo T I 198. Gua, Major product : CCl, . 1 . 4 cl @ ©) CL © Cw @ . i 199. Which of the following compounds * produces-1, 5-cyclooctanedione on ozonolysis? mO OD 0D oC H am) —BuICCh , Major product : i i . ‘N Ne . . @ Co (b) OO (©) se (d) All of these Bra. © © [GRB Advanced Problems in Organic Chemistry for JEE na ©, Major product : ‘OH Crk 202. “il, HCLU Mole) , Major product : 204, H,C=CH, +CO+H, |] ) Ay oN, ow @) 1 ch 203. O + Bry (1 Mole)—©C!y Major product : Br, . B Br Br _- OC 9 D Ae G ‘Br ‘Br Bi Br . Co2(Co}g 100°C, High P OH . . w A ) a" of=o oA" Oo 205. =r -HOCL, Major product : CHy CH, CH,—OH CHs, CHy—Cl @ ® HY” No} Hy” Non CH. CH,—Cl cit—on o. si OX “C cathe 4, Major product :Hydrocarbons (Alkane, Alkene and Alkyne) das () to matorrate: How > + i — >> Major product : @ 8h () ne we {@) No reaction on Bs ENO, y, vis A 2S qT COOH ° 1 I {c) 0 @ yo Oo” . of CH; a “3 + ie H —45. Major product : OCH; CH; ore nO @178 GRB Advanced Problems in Organic Chemistry for JEE HO QO ‘ 211. + ‘OH —45 Major product : 55S 212. ys +Cibh, Es, Major product : . a ort ort © we ® x : 1 Hh, OCH; 213. ~a-22., Major product: OCH OCH; @) CH . (>) H2 OCH; OCH; I CHI © @ : ‘CHa I 214. Find out nature of product obtained by selective bromination of following reactant : Hy Bry — hy - We CH, , (a) Meso. (b) Diastereomers, {c) Enantiomers (d) Homomers179 Hydrocarbons (Alkane, Alkene and Alkyne) 215. Devise a synthesis of following compound from cyclopentane : ox ‘Br Br Cl, ale.KOH Bry Bry C250? Br2,CClg (a) —> ——> (b) — by CCl Br, (d) None of these . Br_alc. KOH NBS © CCl 216. Which of the following alkene will give enantiomeric product on reaction with HBr? ahr oA, oJ o> = 217. Draw the product of following reaction with stereochemistry : H HAC “a OH HCo , OH 218. Devise synthesis of following compound from cyclohexene : CN of “ HBr (a) Addition of HCN 2 Hz NaCN, NBS HCN H®/H20 (©) > @ 4,3, > - 2HCL 219, 4-————> Cl cL Reactant ‘A’ is:180 GRB Advanced Problems In Organic Chemistry for JEE @ . © ay (@) Allof these AN’ CFs 220. one HBr 2.1,0 x COOH On ) 0) Crs uN cl cl © CFs (@) None of these 221. * Suggest the product of following reaction : z 1 HgOAC , lB NaBHy | Los A, (@) Allof these . 22, p= 2 @ c=C, Ne uw” Ncw, oh é Y fa v mn H3 Hy 1 2. Which of the following orders are correct regarding stability? "COCO 9DO H: H. SQ CH Cat (9) . C=Cth> Nad @ Yat > Yad Ne - HC” W Cn H” Na HH Now: HG pr 3. c=C, — H;C-—-C=C—CH; BY Ny Which of the following reagents can be uséd for above conversion? (2) Zn/A (b) Mg/A (©) Nal/acetone (d) Alc. KOH 4. The correct basicity orders are : é % e 6 (@) CH, —Cth, H,C—CH Ss e (c) CH; cn, > HC=C (d) H,C=CH> H—C=C Toa “ge Products :Hydrocarbons (Alkane, Alkene and Alkyne) H;C. 0. ont Se ” uc 6. Choose the co correct comparisons : cl st AA @ a (py we wea BC Cs (b) J > c= (M.pt) H Hy H” H Ch ney © we , og, Reactivity toward HB) jC CH; H: op ° on @®pt) 7, Which of the towing reactions give meso product? _ Hy H HC, CH: SL Bry, CCl \ Scola KMn04 .- @ pas () Ww =C aes me n is A 4 © = ce Cold KMnOs, (gy Cys Bu, CCl H ‘CH; 8.. Which of the following reactions give diastereomeric products? HgC CH; NZ c @ ay Br, HzO () Br, CCly H H . CH Hy Hy H 4 © mPBA « d) pre Os04 H ‘CH H3C” ‘CH,CH3 9. Mark out the correct comparisons. (a) 3°H > 2°H > 1°H (reactivity for bromination) ) AQ < S=CH, (stability) ©) A < =Ch, (reactivity toward HB) LaA< S=cr, (reactivity for catalytic hydrogenation)184 GRB Advanced Problems in Organic Chemistry for JEE CH, 40 Products are : oby ob><,, 0OK, on 1 See 5 m-CPBA mCPBA, 4 10 B Choose the correct statements regarding above reaction : (a) Product. is optically active (b) The conversion of alkene to product B is a stereospecific reaction (c) Product B has chiral molecule (d) Formation of *4’ is syn addition reaction 12, Which of the following reactions are not feasible? (a) HC=CH + KOH —> (b) HC=CH+NaNH, —> 6 (c) HC==CH+NaOH —+ (@) HC=Ck® +(CH;),C—Br —> 13. The following synthesis cannot be carried out by : . ] CH=CH, CH=CH Oo = ct I = Cl ICUCH;COOH —ICV/CH;COOH Zn, dust ay Ss > ss HOCVH® — Clp/Fe —ICV/2nCiz__ NaOH, A. (b) ———> _ ———> —— (excess) HOBr, H® Cla/Fe — ICVZnCly ~~ Zn dust, CH;COOH (ce) SO {excess) Bry/CHjCOOH Clp/Fe —1CI/CHyCOOH NaNH. . . (d) 3! 3s 2fFe 3 aN (excess) 14. 1-butene is formed in reactions : A CF;CO3H . (a) ow 4, 6) AAs ae ' . | @ e 4 e oun u-> @ wy 3_Hydrocarbons (Alkane, Alkene and Aikyne) 185 NaNH, — Ph—CHO. MnO2 15. Bu—C=CH ——> 4 ho” B—-C Compound C of the reaction cannot be : CHO HO =C—Bu (a) (b) =C—Bu HO (c) qd) C=C—Bu 16. Acetone is the major product in : ‘ H?O 1 H,C=C=CH, —> Hg’? /H,S04 Wl HyC—C=CH ————> BH;.THF HT Hj,C—C=CH 5 H207/OH @t (b) 1 @ m (d) None of these 7. Which of the following can be prepared by Wurtz reaction? (a) CH,CH; (b) CH,CH,CH,CH; © HCC CH, @) CH; HG cH, \ CHs CH; AO CH;CH)CH; (a) Compound 4 i sf > > (b) Compound 4 is H;C—CH, —CH, —Br (c) Reagent B is Hy/Niat 120°C (d) Reagent B is LiAIH,186 GRB Advanced Problems in Organic Chemistry for JEE 19. Which of the following molecules of alkane will give only one monohalogenated product on reaction with halogen in presence of suntight? (@) H,C—CH, (b) H,C—CH,—CH, (©) (HyC)4 @ (O}-cu~O) 20. Which of the following methods yield saturated hydrocarbon? BH; CH2N2 —CH=CH = (a) R 2 Gaoont (&) R-CH=CH, —> HY © RAA* Suge, @ Cr Huon cao 21. Which of the following reactions wili give result as alkane as major product? : . Br @) AA LiAlHs ) a NaBH, Cl NaBH. © >—c HAH, @ A” a 22. Which of the following alkanes cannot be synthesized by the Wurtz reaction in good yield? @Y~v™ yw o”nx @ XA 23. Which of the following reactions produce the same product? (a) A _Braby, _Naletber or», NaOH, Electrolysis OOH COOH o><, Myether, _ CHsBr @ 4 Red P+ HI coor 24, How will you distinguish compounds 4 A and B by using laboratory reagent? HC=C’ (@) A reacts with agNO,/Nt1O8 (b) A reacts with CuCl, /NH,OH (©) B does not react with AgNO; /NH,OH - @ B reacts with CuCl, /NH,OHHydrocarbons (Alkane, Alkene and Afkyne) 187 25, Predict the products of following reactions : H | C. ,C=CH oY Cc | H . (a) Ais Ph—CH ,—CH, —CH, —CH, (b) B is Ph—CH=-CH—CH=CH, (c) Ais Ph—CH=CH—CH=CH, (d) Bis Ph—CH,—CH, —CH=CH, 1. NaNH2 Hp 26. H,C—C=CH —— B 2.CH;CH)Br © Pd-BaSOg (a) Ais H,C-—-CH, —C=CH (b) Ais CH; —-C2==C—CH,CH, HC CHCH3 Hc (c) Bis 4 . (d) Bis De W H H 2/980. KMn0, a. H,c—cacH SEE, x Sy, ou ° ll (a) X is HyC—C=CH (b) X is H;C—C—CH, ° (0) Y is Hj;C—C—OH (d) Y is HCOOH AC . H- 28, HC a Y core Sy Zz: z (@) X isHjC—CH=CH—CH, —(b) X is HxC—C==C°Na® OH | (©) Yis HyC—CeC—P-— CH @ Zis HyC—C=O—F= CH, CH; CH, = i $2 3% 29. AEA BuLi x CH3I y Hg'?/H30 Zz: CH 8 . c=cL? c=c” (a) Xis A\/ (b) Yis AZ 9 (c) Zis WY (@) Xis AK: oO188 GRB Advanced Problems in Organic Chemistry for JEE 30. Which of the following solubility orders in water are correct? (a) HyC—C=CHCH,—0—CH, (©) H»C=CH—CH, CH;CH,CH, Br KCN 31, 1H, : Crom atta Aa: CHy—C=N CHy—Br wan x waist XK ‘OCH, ‘OCH; CH;—Br CH,—C=N . @A w( @ Bia ‘OCH; ‘OCH; 32. Write the products of the following reaction : CHNad HCCh; + ou (a) A _ (b) Ais { (©) Bis ><] (a) ais) ><] cr ci HC Hop a 6 DyINi HW ‘CH; CH; CH, CH, cH D H H D p—\—u fp @y H. 5 \—H On D @ \—p CH, CH; CH; CH; CPB, oO? 34, Cyr AE _,8 Major): NaOH Ho 7 Major)Hydrocarbons (Alkane, Alkene and Alkyne) 189 CH; @A wo (b) B ‘oc HOH , CH; CH; (0) Bis| OH @ cx Kon MOH Ou H . Which of the following carbocations would you expect to rearrange? SCH, CH; 1) @) {b) CH, CH; ‘ pu e © (a) HC’ ‘CH—CH; 36. Select the correct statements : (@) addition of Br, on trans-2-butene gives erythro product (6) addition of Cl, on cis-2-butene gives threo product (6) addition of Br, on cis-2-butene gives racemic mixture (@) addition of D, on cis-2-butene gives meso product 37. Which of the following will give allyl halide? $0,Cl, Cla, 800K. -@) H,0—CH—cH, 2, @) H,C=CH—CH, PS (© H,C=cH—cH, Ss (@ HjC—CH=CH, + HBr “22, 8, Which on the following reactions will give least substituted alkene? wy po sos, Cone. #804 wo | Me3C-—OK® Alc. KOH ad Cs) SRO? M8, okW - oN Br 9. Which of the following reactions will give alkyne? oa x, (0) Xs Nh, ch190 GRB Advanced Problems in Organic Chemistry for JEE Br Br Zn,A | I 2 () WCF cH 4g HyC—cacH B84 Br Br 40. An organic compound on (eaction with O; followed by Zn and H,0 gives CH cron, lc, ‘The structures are : - a) Kayo “OO « a @) 41. Which of the following reactions are correctly represented? (a) R—CH=CH, +HCl —> Rott a H,0. (b) R—CH=CH, +H > R—CH,—CH,—I H,0. (©) R—CH=CH, +HBr ——> R—CH,—CH,—Br hy I H,07 | (4) R—CH=CH, +HI ——“> R—-CH—CH, v - Which of the following give allylic substitution product? A ee, SEE DAS © AS ADS 3. Which of the following reactions are correct? Brit oN @ (_.) Pees, Br “Br CHsCOH , HR © Sons) Q- ®, oo wn wh ©) [Hydrocarbons (Alkane, Alkene and Alkyne) 191 44, Which of the following are correct for the addition of X, on alkene? (a) Reaction involves cyclic halonium ion as intermediate (b) Reaction involves carbocation intermediate (c) Addition is anti addition reaction (a) Trans alkene (Symmetrical) gives meso product “45. Which of the following will react with 1-butyne? (a) AgNO, +NH,OH (b) Cu,Cl, +NH,OH e (©) Na . (@ KMn0,/OH Which of the following do not give rearrangement of carbocation in the addition reaction of alkene? ° 46. (@) Br,/CCl, (b) HBr (¢) HBr/H,02, hv () 030, 47. Which of the following will give acetone? . He"?, H2S0, BH (a) Hj,C—C=acH = (6) CH; —C=CH 35 OH, H,0 o> Bess Se (@ HC=CH+CH,OH —> 48. Which of the following compounds can exhibit geometrical isomerism? (a) HyC—CH,—CH=CH—CH; —(b) HC OH : Be. Scan” @ em © H a HC cH; 49. Which of the following products will form by given reaction? AW XBS_, hy . Br ‘ @ 7Y~* (b) HBr © DA @ PRA Br 50. In which of the following reactions the correct product is given? CCl; OH Si [Ce (a) AA AE ti804 x) oC) — 1,7 oH Br H°MH,0 é HBr © es vn OA ge Av192 GRB Advanced Problems in Organic Chemistry for JEE (EE3S3GSS Linke COMPREHENSION TYPE I Passage-1 Conjugated diene reacts with unsaturated hydrocarbon in presence of heat to Produce six membered cyclic product, this reaction is known as Diels-Alder reaction, For this reaction conjugated diene should be in cisiod form. Aromatic hydrocarbon do not give Diels-Alder reaction : oy C—H Qo SY Diene — Dienophile Intermediate 1. Which of the following conjugated unsaturated hydrocarbons will give Diels-Alder reaction? ON Zz A @ © € © Cen ® a S Sy 2. Which of the following Diels-Alder reactions is fastest? Oz Oz oCG C 4 ot “4 NO 102 A oo A (e) + | = qd) ~ N-H+ | eed 3. Find the product of following reaction : 4, CN CN @) (b) ‘CHO ‘CHO COOH {c) (@) No reaction COOHHydrocarbons (Alkane, Alkene and Alkyne) 193 Passage-2 Addition of X, on alkene is electrophilic addition reaction. Reaction proceed through the formation of 3-membered cyclic halonium ion. Nucleophile X® attacks from backside of cyclic halonium ion hence total reaction is anti addition reaction, If this reaction proceed in polar solvent then solvent itself acts as nucleophile. \ = x Mechanism : x 2 NOY VY + C= —¢ AN Wan ¢ x. YY “YS — i i Z| \ xe Xx 4. Which of the following statements is incorrect? (a) Symmetrical trans alkene gives 2 products on reaction with Br,/CCl, (b) Symmetrical cis alkene gives 2 products on reaction with Br, /CCl, (©) Trans alkenes give erythro product (d) Cis alkenes give threo product Ch (1 Mole) > CC : \ CH: Cl ca CH: Cl cl ca @ ) © @ Cl N \ a ch mm 7s Ch, CH;OH. = — Ph Ph H—+—Cl H——Cl ©) yt ocx CH3;—}— Cl yt 3 H CH; Major product :194 GRB Advanced Problems in Organic Chemistry for JEE Ph Ph H——Cl a) H~-~)-—- OCH H;CO—}—H cl——H CHy CH; (©) Passage-3 Addition of HX on alkene proceed through the formation of carbocation, This reaction is also known as Markownikoff reaction. According to Markownikoff’s rule addition of electrophile occurs on that carbon of alkene which have more number of ‘H’ atom. x |. Ph—CH=CH, + Ph—-CH—CH, +Ph—CH,—CH, —¥ Major Minor , Mechanism : H—-X == H° +x° Ph Ph Sc=cr, 82, N&_cny+pn—cw—Ba, H” Ww More stable Less sable Ph Xx. ey ye SLO x H ‘CH; Hy aa C#y_EGC’ Enantiomer 7. Which of the following alkenes can produce diastereomers? (@) CH;—CH=CH—CH, . ) CH=CH—CH, H, CH; CH; : ‘© . (dj CH;—CH—CH, 8. Which of the following alkenes will give Markownikoff reaction? Hay . (@ F,C-—-cH=cH, “4 (») H®N—cH=cH, BSS HBr CH (© 0.N—CH=cH, 5 @ emer, as, CHs : 9. Arrange the following alkenes in decreasing order of reaction with HBr : CH” ql CB CH; \ ns w= emer CHy Hct CHy—0—CHS . 8 0 ) &) (a) P>O>R>S (b) R>O>P>S () S>R>Q>P @Q>R>P>sHydrocarbons (Alkane, Alkene and Alkyne) : 195 Passage-4 Alkene and alkyne both undergo electrophilic addition because of 1 electron density, they behave as electron rich species, alkenes are more reactive toward this reaction because the intermediate formed when an E® adds to an alkyne is a vinylic cation whereas the intermediate formed when an E® adds to alkene is alkyl cation, which is more stable. “™ pe ® R—C=C—H —> R—-C=CH Vinyl cation : Ee 2 R—CH=CH, — > R—CH—CH Alkyl cation Ss HCI(1 Mole) ne oChy .. ©) by s ©). a Cc (d) . Y . Cc CF;COSH ML. == AA yp (a) 2 {b) ° 6 G (©) OH OH » 12. In the reaction : OH}, NaHCO; XY a“196 GRB Advanced Problems in Organic Chemistry for JEE f 1° O—C—OH . OH OH. {a) (b) 1 oO 1 Oo I ©, @ 5 ‘0: ‘0 Oo Passage-5 : CH CH,=CH—C_Br CH3MgBr CH; B Hp, Pd-BaSOq E CuCl 2CH=CH Wao 4. ‘NH,CI (y.THF H®, He"7/HySO4 D Me 13. Find structure of compound A : a ' (a) CH, —CH—CH—CH, (b) H,C=CH-—-CH=CH, (c) HC=C—C=CH (@) H,C=CH—C=CH 14. Find structure of compound E : : : Abb (a) HC=CH—C=C—CHy—CH=G ‘CH; Jb (b) HyC—CH,—C=C—CH,—CH=C ‘cH: HyC—CH. * CHy—CH= © Sond cits H H HOCH @ weak Ons H CHy—CH=Hydrocarbons (Alkane, Alkene and Alkyne) 197 15. Find structure of compound D : O HO, (oO H HH. G HO, 0 b) d) a YY oe “Y o VY) @ YX 0° H;C” ‘o O OH H3C” “OH Passage-6 P(CsHoBr) NaNH, v Decolourise Br) water O3 Q and cold KMn0, 2—Wyeg? = (No reaction with Na) Lindlar catalyst Na/NH3(2) R Ss (CsHio) (CsHio) 16. Which of the following is compound P? orv~0 wor © AN Ow , Br Br 17. Rand S are : (a) position isomers (b) enantiomers (c) geometrical isomers (d) functional group isomers 18. Identify structure of compound T : ‘ - Oo ° {a) CH; —C—OH (b) () Cy CH, —F—OH @ OH 1 : ° ° Passage-7 . Hydroboration oxidation reaction is a process of addition of H,O according to Anti-Markownikoff’s rule. BH3.THF ~ CH,CH=CH, ————> CH, —CH,—CH—OH H202, OH Reaction is regioselective, Regiosclectivity of reaction is increaseid by using : hindered boranes. THF (Tetrahydrofuran) is used to control reactivity of borane. c—GRB Advanced Problems in Organic Chemistry for JEE 198 : CH;—CH=CH, — CHy—CH==CH, + |) —> CHsCH,CH,BE, H—BH, H-BH, 2CH: H=CH; . eR Te CHCHCHa)s B or RB R=CHjCH;CH)— e 8 H—O—O—H+0H —> 0—O—H+H,0 R R _ oR l wh ° le z R-B4/+0—0 -H— R00 R—B—OR : oH R R OR . 20H | — = RO—B--OR ba 3R—OH + BO; BD3.THF Cf aa? Major product : ee OH CH; @ Cf ©) Cf, © Cfo @ Cf . OH H HP HOF ‘ BD3.THF . 20. Nome’ + Ce H~ coon 202,60 CooH COOH cooH cooH Ki D H op p—+—-# D » Oy op © p On op © 4 OH * COOH, COOH COOH COOH BH3.THF 1. CH; —C=sCH ———— Major product : H207,0H r 0 (a) CH;—C—CH, : (&) CH, CH=CH, : OH oH a (@) CH; —CH, —C—H | (c) CH, —CH =CH,Hydrocarbons (Alkane, Alkene and Alkyne) 199 Passage-8 ‘Alkane may be prepared from alkyl halide by Wurtz method where alkyl halide reacted with Na in presence of ether. 2R—X aay R—R +2NaX. Mechanism : 2Na —»> 2Na® +27 x 2e + RX RP+ Xe [X Re + SGX, RR +X? 2Na® +2x° ——» 2NaX Na/ether. 22, CH;CH,—Cl "> Which of the following products may not be formed? (a) CH;—-CH, * - (b) CHy—-CH,—CH,—CH, (©) CH, = CH (@) CH, . CH, ‘Na/ether 23. CH Br WS", Major product CH, CA, CH; Je (@) meme (b) CH, -C—C—CH, Hy» 1] CH; CH; CH; © CHF CH,CH; (d) No reaction cH, . 24. Which of the following compounds is most reactive for Wurtz reaction? Br . Br (a) CH; —CH, —CH, (b) Br / CH,” ©) (d) CH; —— Br CH;200 GRB Advanced Problems in Organic Chemistry for JEE Passage-9 Hydrocarbon 4 (C;H,2) was treated with BH,.THF; H,0,, NaOH to produce « B(CH,40) as only product. Reaction of B with TsCl/pyridine followed by KOH gives C (isomeric with ‘A) in addition to the olefinic products. Treatment of C with ozone followed by 2n/AcOH produces only compound shown below : CHO CHO H3C . 25. What is correct structure of ‘4"? ©) O ® C) C) a @ cy 26. What is correct structure of ‘B"? OH OH (a) (b) (c) @ : ‘OH OH 27. What is correct structure of compound ‘C”? {a) b) O ©) O @ Passage-10 Oxymercuration demercuration reaction is process of addition HO according to Markownikoff’s rule without any rearrangement. ou (OAc)2, H2O. | cH,—cn=cH, T80*2129 cy cucu, NaBHy, OH Mechanism : e e- Hg(OAc), == Hg(OAc) + AcO OAc 7 Ca cept urge 5 cH;—CH—CH, ~ CH;—CH—CH; on La Q OH H OH lg? an fo WOR AY WHHydrocarbons (Alkane, Alkene and Alkyne) 201 8 Base OH is used to neutralise H® produced during the reaction : CH, | Hg(OAc):, H20 28. & \-cmonn HeOA02 0, waior product : " NaBD;, OH CH, (a) Poo CH, OH . CHy (©) Ph—-C—CH, —OH CH; | () Ph—€-—CHD OH CH, (d) Ph— goo . D : op CHy (OAc)2, CH;0H 29, CH; —-C—CH=CH, He(OAC)2, CHa0F product: { NaBHy, OH CH, OCH, CH, CH, OH @ Cy CH—CH, CH, CH, OCH, | ©) Cy —o— CH—CH, - CH; L INH: oO) In Hg(OAc)p NaBH,SOH - On . NER (a) H | N. oe | ) hy —F— CH—CH, CH; (d) No reaction (b) ce @ Both (a) and (6)202 GRB Advanced Problems in Organic Chemistry for JEE Passage-11 Free radical substitution chalcogenation is shown by the compounds having at least one H-atom an sp°-hybridised carbon atom. Here substitution is due to free radical formation in presence of sunlight or heat or peroxide. The abstruction of . H-atom is on the basis of stability of free radical formed. ms Hy ~CH, 25 CH ‘CH —< er pe sR OQ P 31. Which of the above hydrogen can be abstracted casily by halogen in presence of sunlight? @ P () @ OR @s 32. In the above reaction how many monobrominated products are possible? (@) 3 () 4 (5 @7 33. Which of these H-atom can be substituted to get an optically active halide? (a) P _ 9a OR PARSE MATRIX MATCH TYPE li 1. Column (1) Column (1) @BAAA = O P. Red P+HI Br ° 0) Cl Q. Nalether ‘OH ‘OH > : i ° ory — NW R. NH,—-NH,/OH 98 COOH coo | @ oy or S. Zn-Hg/HCI 2. Column (1) Column (I) ” : cH, | 20H, CR x — CH, CH—CH, P. LiAIH, cH; ~ CH; CH,—X CH () | — | Q. Na, dry ether" CH,—X CH,4 Hydrocarbons (Alkane, Alkene and Alkyne) (CH, FH x — Cus tlt R. Mg, dry ether CH; CH; ¢ : Hy Hy @ He —¥ 3 CH= S. Znl& CH, CH; 3. Column (1) Column (ID) . cl (a) OC Lin, CCl, CK P, Rearrangement Cl : ) A Sab, CLA Q. Carbocation Br ‘CH30H ©) sh = »*< R. Free radical @ ~* ning ay $. Cyclic transition state 4, Column (1) Column (I) @ O--e6) P. Reacts with Hy-Pd/CaCO, 203 (b) Oe a Q. Trans alkene will form when reacted with Na/Liq. NH3 (©) Oe ane _ BR. Reacts with ammoniacal - AgNO, (@) H-C=C S: On oxidative ozonolysis produces CO, 5. Column (1) . Column (11) . BC es (a) HyC—C==C—CH; —> C=C P. H, Pd-BaSO, We Sy me A (b) Hy3C—C==C—CH; —> ==C Q. Li, Lig. NH Ncw,204 GRB Advanced Problems In Organic Chemistry for JEE (&) H;\C—CH=CH—CH, —> H. 2 CHC CH “0-0 . Columa ® a © -_ Ph. HBr QA ow” HC 225 7, Column (1) HC. @) C=CH—CH; So HSC” Ag20 Hg"?, HySO4 (b) H;C—C=CH ————> ll Red P + HI (©) H,C—C—cH, ——> o {I NoHy. OH (a) Hy0—FH— Cl, CCH a 8. Column (1) (a) Markownikoff product R. HN=NH, A S. ByH,,CH,COOH Column (i) P. Free radical Q. Enantiomer R. Diastereomer ‘S. Carbocation Column (11) P. Reduction oO Q. CH;—C—CH, R. Oxidation reaction SN Column (12) HB; P. CH;—CH=CH, ———> H)02, bv205 Hydrocarbons (Alkane, Alkene and Alkyne) or , HC CHs (b) Anti-Markownikoff product \ 4 CHCh + KOH : . C=C. > H “ ‘ H (c) Peroxide effect (4) Mixture of stereoisomers . Column (1) @ Conc, H2SO4 a OH cl CoHs8/C)HS0H b) Iw, cl Br Alc, KOH w@A —_— HCl 2 Operon 5. CF, CH=CH, 85 Column (ID) P. Hofmann’s alkene Q. Saytzeff’s alkene R. Transition state S. Carbocation 10. Column (1) Column (0) CH, : CH; @ a P. 3 different products les wy Os CO, will 6) P= CH—CH CH=CH g,0° Q. CO, will produce HC 0: () HjC—C=CH —> R. Oxidative ozonolysis Ag20 O: (@) HxC—CH=C=CH, = S. Reductive ozonolysis 11, Column (D) Column (1) HC, CH, @ =< Oe MnO, P. Racemic mixture H H EC. AS Be, CC () ac“ Ba. CC, Q. Erythro H H‘ : 206 GRB Advanced Problems in Organic Chemistry for JEE \ CFC yt —CCOH R. Threo Teno . ne @ at" : “ exoeu, S. Meso product . ‘cu; 12. Column (1) Column (11) a) P. Dicarboxylic acid will be formed when reacts with not alkaline KMnO,. 6) Q. Decolourise Br2/H,0. © R. Dicarboxylic acid and will be formed when reacts with: 03/40). @ S. Number of allylic hydrogen is odd, (ESET INTEGER ANSWER TYPE PROBLEMS [| 1. Find out number of dimerize products obtain by following reaction, HyC—Cl + H,C—CH, —Cl + H,C—CH, —CH, —a1 2. How many mono chlorinated products may be obtained when the alkane shown below is heated in the presence of Cl, 3. How many of the following reactions, leads to the formation of diastereomers. Ph H mB ; Me. @ ‘scr+cu,—42 5 o) SS BS Ww CCl,Hydrocarbons (Alkane, Alkene and Alkyne) 207 CH; Phy HBr x » HCL © nt ea? @ i och CH CH; Ph, HCL f CI @ CL, ae, ) te, , CH; 4, Identify number of chiral centers present in product obtained by following reaction. Bry y cc, ~, CH; H 5. How many of the foliowing addition reactions are syn addition reaction. H. CH H, Foe a BQ > Ni {a) C=C eer, 7 b) =< asa We H “ D* D (© HyxC—C=C— CH, BETES, (a) CC C—CH, BBs THF >THE Cold KMaO, oC Se or CH; _1:PaCOsH, Br, + H,0. ® on Fae ») —ee CHy : 6. Of the following reactions how many reactions are considered as oxidation reaction. 0: @ > 2 (6) Ss kMn0/8H ‘Ph ‘Ag,O a oN OSs! (a) ~~ TEM, 9 ocr CH,CO;H wo oe NaBH,208 GRB Advanced Problems in Organic Chemistry for JEE 1 In this reaction which ring will be reduced, by hydrogenation. 8. OF the following compound, find out numbers of conjugated unsaturated hydrocarbon those would not show Diels alder reactions. C8: O:-0°0. C6) XK Oe 9. How many different products (excluding stereoisomer) can be obtained by following reaction. oe HCI, CCl, 10, Examine the’structural formulas of following compounds, and find how many compounds will produce CO, on oxidative ozonolysis. > HyC—C==CH > Ph—CH=CH, > -\ZrnHydrocarbons (Alkane, Alkene and Alkyne) | 209 eS! Exercise-1 : Only One Correct Answer Level-1 2. @) 11. (b) 21. «) 31. (a) aL: (d) Level-2 1.©@ 2) 3@ 4© 5@ 6©@ 7@) 8 @) 9. (6) 20. @) 11 (a) 42. (b) 13. (6) 14, ©) 15. (@) 16.) 17. () 18. (b) 19.4) 20. (A) 21. (©) 22. (@) 23. (c) 24. (b) 25. (a) 26. (cd) 27. (6) 2B. (©) 29. (b) 30. (A) B1. (©) 32: (@) 33. (a) 34. (A) 35, (d) 36, (@) 37. (b) 38. (b) 89, (b) 40. (a)} . 41. (@) 42. (b) 43. (c) 44. (c) 45. () 46. (a) 47. (d) 48. (a) 49. (6) 50. (b); BA. (c) 52. (d) “53, (c) $4; (a) 55. (c) 56. (b) 57. (b) 58, (b) 59. (c) 60. (c) G1..(2) 62. (©) 63. (a) 64. (c) 65. (b) 66. (b) 67. (c) 68. (a) 69. (6) 70, (C) 71. (b) 72. (b) 73. () 74. (4) 75. (b) 76. (c) 77. (b) 78. (2) 79. (¢) 80, (a) 81. (b) 82, (a) 83. (c) 84. (b) 85. (c) 86. (a) B7. (b) 8B. (c) 89. (d). 90. (b) 91. (c) 92. (@) 93. (c) 94. (d) 95. (c) 96. (b) 97. (c) 9B. (a) 99, (c) 100. (b)) 101. (a) 102. (b) 103. (a) 104, (d) 105, (a) 106. (c) 107. (a) 108. (b) 209. (c) 120, (d} 14. (a) 112. (c) 113, (d) 144. (d) 128. (b) 216. (c) 117. (6) 118. (a) 139. (c) 120. (c). 121, (b) 122. (d) 123. (b) 124, (2) 125. (6) 126. (a) 127. (6) 128. {c) 129. (2) 130, (b) 31. (c) 132, (b) 133. (b) 184, (a) 135. (d) 136, (c) 137. (b) 138. (c) 139. (@) 440. (b) 41. (c) 142. (c) 143. (d) 144, (2) 145. (d) 146.<(b) 147, (b) 148. (c) 149. (b) 150. (0) '54.- (d) 152, (a) 153. (b) 154. (c) 155. (b) 156. (b) 157. (d) 188, (c) 159. (a)'160. (6) 62. (a) 162. (d) 163. (a) 164. (d) 165. (2) 166. (c) 167. (b) 168. (c) 169. (4) 170. (a) 74. () 172. (c) 173, (2) 174, (b) 175. (c) 176. (b) 177. (4) 178. (d) 179. (©) 180. (A) 181. (c) 182. (d) 183. (2) 184. (b) 185. (b) 186. (d) 187. (b) 188. (d) 1B9. (¢).190, (b 191. (c) 192. (c) 193. (c) 194. (b) 195, (d) 196. (b) 197. (2) 198. (c) 199, (b) 200. (c) 1. (d) 202. (a) 203. (c) 204. {d) 205. (b) 206. (b) 207..(e) 208, (c) 209. (c) 210. (a) 12. (c) 212, (a) 213.. (b) 14. (c) 215. (c) 216, (b) 217. (a) 218. (b) 219. (a) 220. (b)} 1, (c),222, (2) 223. (0) (2) 225.0) _ Exercise-2 : More Than One Correct Answers “h(a,b,cd) 2 (ac) 3 (bc) 4 (bc,d) 5. (abc) 6 (bd) 7 (ab) 8 (Bc) 9 f@b,c) 10. (@, b,c) “IL (b,c) 12 (a, 6,4) 13. (a,b, d) 14. (4.b,6,d) $8 (abc) 16. (Gb) 17. (bd) is 18. (@,c,d) 20. (@,b, c,d) 22. (@b.d) 22. (@,c.d) 23. (2,b, 6,4) 24.64, (2) = 26, (, an Pn (Ds ©) a2 ine D6.) 2.06) 30s (8,8)210 : GRB Advanced Problems in Organic Chemistry for JEE [3 Gd 82 Ge) 43. (Ge) 34 bd) 35. bd 26.6,b.cd) 37. (a,b,c) 38. (b,c) 39. (a,b,c) 40, (a,b,c) 43. (a,c,d) 42. (a,b, d)) 43. (a,b,c) 44. (a,¢,d) 45. (a,b,c, d) 46. (acd) 47. (a,c) 48. (a,b, 0) B,D, BB. (2, b,c) - we Exercise-3 : Lint Comprehension Type _ 1 @) 2. @) (by 4. fa} 5. ) . (b) ‘10. @ @); 11. (b) 12. ©) 13. @) 14 (©) 36. (@) 16 @) 17 ©) 18. 0) 19. (b) 20. (c); BL.) 22.) 23. (@) 24. tb) 25. (c) 26 () 27 (@) 28. (b) 29.) 30. “| 34. (J) _32 (©) 23. (b) - — a Exercise-4 : Matrix Match Type ee eee ee Tr (b) 3 R; IPRS @ooRr | . . (DN AQIS; ()4P; (a) 3 P,Q ' "3, 9S; (b)9R: P.O; @>P.Q i 4. (P,Q; (b) 9 PLR, S; P.O; @)>PRS 5. @9P.RS; (90: (RS; @30 | 6. @)> 9, {b)- B.S; ©>P.0; (6) P.0 “2. (a) OR; (b) 3 OR: @>P: ()—P.S | BAR: (b) 9 P,S; (> P; GIR 5. 70.8; () > ORG (PAR GPR | 20, (2)-»P,S: (b)P.0,R; (0.R: (4) P,Q,8 ' Aa. (2) 0,8; )> PR: 39,8; @> OS 2 (POR WAPORS — OBRORS.. O20 | Exercise-5 : Integer Answer Answer Type Problems Lb 2@) 2O 2@la@ 2@ L@_3® 2 13 @ Q00