3. 4 HYDROCARBONS (ALKANES) On halogenation, an alkane gives only one monohalogenated product. The alkane may be: (a) 2-methyl butane (b) 2, 2-dimethyl propane (©) cyclopentane (d) both (b) and () Which of the following compounds can be best prepared by Wurtz-reaction ? (a) Iso-butane (b) n-butane (© mpentane @ lso-pentane A hydrocarbon A (V.D. = 36) forms only one monochloro substitution product. A will be : (@) iso-pentane (b) neo-pentane (© cyclohexane (@) methyl-cyclohexane Ethyl iodide and n-propyl iodide are allowed to undergo Wurtz reaction. The alkane which will not be obtained in this reaction is.: (@) butane (b) propane © pentane @ hexane c,— ff —CH,—CH, —22-> CH Number of chiral centers generated during monochlorination in the above reaction : @1 m2 ©3 @47 9. 10. 11. CH,Cl— CH, ‘Above conversion can be achieved by : (@) Zn/H* (®) LAH, (© Mg / (ether) then H,0 @) all of these n-Butane —2x4™_, Give the total number of monochloro products including stereoisomers), which are possible in the above reaction. @2 ) 3 o4 @s5 CH, +Cl, —“ +CH,Cl+ HCl ‘To obtain high yields of CHCl, the ratio of CH, to Cl, must be = (@) high ©) low © equal (@ can't be predicted Double bond equivalent of cubane is : Cubane @4 ws ©6 @7 How many bond cleavages are required to convert cubane into non-cyclic skeleton ? 44) Cubane Non-cyclic skeleton (a2 3 4 @s Draw an energy profile diagram fora three step reaction in which first step is slowest and last step is fastest. (Assume that reaction is exothermic) re Pe| @ o) progress of reaction ‘progress of reaction PE, o @ None of these13. 14. 15. 16. 17. stereoisomers. @4 5 6 @7 NDy—ND3 ) #20; Product (P) is : D ot D " @ ) > «o pA) both (b) & cay Hameo Double bond equivalent (degree of Unsaturation) of (A) is @1 2 o3 @4 Arrange the following alkanes in decreasing order of their heats of combustion. cH,— FH cH, —cH, CH, (Gs0-pentane) (8) (ili) CH, —CH, — CH, —CH, —CH @ @>w@> (©) Gi) > @ > GD) © Gi) > W>O @ @ > Gi) > GD Product of the above reaction will be : (a) Racemic mixture (b) Diastereomers (©) Meso (@) Constitutional isomers CH oo 7 CH, +B, —— CHy—CHy Which of the following compound will not be obtained as a product in the above reaction ?18. 19. 20. 21. 22. ——}— # Br @ © Br H H Br CH,—CH3 CH, —CH3 cH Hy H Br Br H o ch, @ H —-— ae 4H Br CH Ct, —CHy Following are the structures of four isomer of hexane. Among the names given below, which correctly identifies the fifth isomer ? CH,CH,CH,CH,CH,CH, (CH,)3CCH,CHy (CH,),CHCH,CH,CH, (CH,),CHCH(CH)2 (a) 2-Methyl pentane () 2Ethyl butane (© 2,3-Dimethyl butane (@ 3-Methyl pentane Which of the following describes the best relationship between the methyl groups in the chair conformation of the substance shown below ? CH, ‘CH, (@ Trans (b) Anti (© Gauche @ Edlipsed Compare the stabilities of the following two compounds (A) and (B): ‘A: cis-1-ethyl-3-methyl cyclohexane B : trans-1-ethy|-3-methyl cyclohexane (@) Ais more stable (b) Bis more stable (© Aand B are of equal stability (@) No comparison can be made Which conformation of ethane has the lowest potential energy ? (@) Eclipsed () Skew: © Staggered @ All will have equal potential energy Ethane is subjected to combustion process. During the combustion the hybrid state of carbon changes from : (@) sp? tosp® (®) sp? to sp (©) sptosp® (@) sp? to sp” Cis —CH, —CHy —cH, “cH, — Gi cls CH; “Above reaction is an example of:27. 29. 30. (@) isomerization (b) polymerization (© cracking (@) dehydrogenation Which of the following has highest chlorine content ? (@) Pyrene () DDT (©) Chloral (@ Gammaxene Pure methane can be prepared by : (@) Wurtz reaction (b) Kolbe electrolysis method (©) soda-lime de-carboxylation (@) reduction with H Calcium carbide + heavy water —> ? ‘The product of the above reaction is : @ CoH © cap, © calor), @ cD, eon] cay ace <) Ethyl cyclopentane Ethyl eydohexane Ethyl cycloheptane o @ a Arrange the compounds I, Il and Ill in decreasing order of their heats of combustion: (a) U>1>m @)I>n>m (© m>n>1 @m>t>0 ‘An alkane (mol. wt. = 86) on bromination gives only two monobromo derivatives (excluding stereoisomers). The alkane is : CHs (@) CHy— CH—CH,—CH;—CH, —@) cyt cH, cy bu, oi, CH, © cH Haar, @ cfc CH, CHy CH; Order of the bond strength of C—H bonds involving sp, sp and sp? hybridized carbon atoms is = (@) sp>sp? >sp? () sp? >sp? >sp (© sp? >sp? >sp (@ sp? >sp> sp? Cp HOH cH OH HGH o ap a) Among the structures given , select the enantiomers : (a) [and (b) Land I (© Wand It @ 1, Mand am32. 33. 34, 35. 36. 37. © a qa ‘The correct order of reactivity of I, I! & III towards addition reactions is : @I>m>1 @i>m5m (© m>t>t @m>i>0 oom Rupp ether_, (ay om Product (A) of above reaction is : "D> 9S «D wD Which of the following reactants is suitable for preparation of methane and ethane by using one step only ? (@) HyC = CH, (b) CHO (© CH, —Br (@ CH3 —CH, —OH How many carbon atoms does an alkane (nota cycloalkane) need before itis capable to exist in enantiomeric form ? @ 4 5 6 @7 ‘Among the following free radical bromination reactions, select those in which 2° halide is the major product — CH, —CHy, oO =~“ nels: wav, ee, ee yy Bryfhv ) aS ae MAA =~ @PARS ©) BRU © PRST @P.QRST (A) + Cl) —"-» monochloro product ‘To maximise the yield of monochloro product in the above reaction ? (a) Cl, must be added in excess (b) Reactant (A) must be added in excess (© Reaction must be carried out in dark (@ Reaction must be cartied out with equimolar’ mixture of Cl; and A Hy —CH, —CH, —CH, Major product in the above reaction is : (@) Racemic mixture (b) Meso (©) Diastereomers (@) Constitutional isomers180 38, 39. 40. 41. 42. ORGANIC Chemistry.for IT-JEE Select the chain propagation steps in the free-radical chlorination of methane. q@a,— 2cr (2) Cl" +CH,—> CH,CI+H" (@) cl +CH, — CHy+HCL @) HY +Cl,—> Hel +cl* (5) CH} +Cl,—> CH,Cl+cl’ (@) 2,35 () 1,3,6 35 (@) 23,4 Hy Bre Monobromo derivatives ‘The number of possible monobromo products is (excluding stereoisomers): @4 os 8 @ 10 Cy ys ea +B —> He ‘OH CH — HE Br will abstract which of the hydrogen most readily ? @a ()b @e @a Arrange the following compounds in decreasing order of their heats of combustion : Py “a ch, CH # CH CH © w @ Gi > G)>@ ©) @>@ > © Gid > @ > Gi @@>@> (CHy—CHy—CH,—CH,—F a ob c¢ 4d Arrange the hydrogens a, b,c, d, in decreasing order of their reactivities towards chlorination: (@a>b>e>d (b) b>c>d>a © b>c>a>d @c>b>a>d (On catalytic reduction (H/Pt) how many alkenes will give n-butane ? @1 (b) 2 @3 @4 On catalytic reduction (14,/Pt) how many alkenes will give 2-methylbutane ? @1 b) 2 3 @4HYDROCARBONS (ALKANES)? 45. 47. 48. 49. (ee ace, How many dichloro products are formed in the above reaction (including stereoisomers)? @) 5 @) 6 o7 @9 Hees oo uy D “p Product of the above reaction will be : (a) Racemic mixture (b) Diastereomers (©) Meso (@ Constitutional isomers Ph— GH, —GH—CHHy ts D Product of the above reaction will be : (a) Diastereomers (b) Racemic mixture (©) Meso (@) Constitutional isomers CH,—cl AD —Huldyetien cuy cH, —Cl Products obtained in above Wurtz reaction is : @ cHy CH, CHy © CHy 9 (@) Both (a) and (b) 9 id CH Rank the transition states that occur during the following reaction steps in order of increasing stability (least —> most stable) : 1 HjC-OH,—> CH} +H, 2. (CHH)g6-OH2—> (CH),C7 + H,0 3, (CHy),CH -OH, —> (CH),CH" + H,0 @1<2<3 @)2<3<1 (@1<3<2 @2<1<3182 ORGANIC Chemistry,for IT-JEE 50. Which of the following does not represent major product of that reaction ? : ® ops cB f © f aa a Br Br © wr. wy Bi Br ® <> tay emer © Br 11 @ & (0) 15 |@|6|@] 7] ol] s.[@ | 9 | om @ | 11] © [12] © | 13.| @ | 14] © | 18.| ( [16.| wo 17.| @ | 18.| @ | 19.| @ | 20.| @ | 21. | © | 22.| @ [23.| @ [24] a | 25.| () | 26.| (©) |27-| © | 28.| (© | 29] (@ | 30.] ( | 31.| @ | 32.] @ | 33.| () | 34. | (d) | 35. | (b) | 36. | (b) 1 37- | (a) | 38. | () | 39.| (ey | 40.| (a | 41. | ca [42.] [43.] © [44] [45-| @ | 46. | w [a7] @ fae. @ 49. | (©) | 50-| () i feat] deFor the given question (1, 2, 3), consider the following reaction. So A. Light is involved in which step of the reaction : (@) Initiation only (b) Termination only (© Propagation only (@ Propagation and Termination 1B. Which halogen will give the best yield of a single monohalogenation product ? @r wa, © Bry @ Ip . How many monohalo derivatives are possible (excluding stereoisomers) ? @3 ws ©s @6 omit Halogenation is a substitution reaction, where halogen replaces one or more hydrogens of Houpsenavce R—H+X,—™5R—X+HK eeaibal sou stan eon ances, ree re— PE. Free radical alkane + 81" Progres of the reaction ogres afthe reaction Citorination ether and Brominain i endothermic and transition sce resemble with prods tonaiton state resem wth produce Chlorine free radical make 1,2, 3 radicals with almost equal ease, whereas bromine fre radicals havea clear preference forthe formation of tertiary hee radicals So, bromine i lee feactve, and more selective whereas chlorine isles selective and moe renctve ‘The relative rate of absaction ofhydzogen by Br* i oF hydrogen by } ‘ (1600) (82) ~ (ay ‘The relative rate of ahewacton of hydrogen by Cl” oF hydroge (5) (3.8) ()A Consider the above argument and answer A to G L-halo-2,3-dimethyl butane will be obtained in better yields, if halogen is : d (@) Bry @) cl, Ok (d) Can't be predicted @d, ©) I © Bry (@) Can't be predicted CH, CH,—CH—CH, 25 product Major product in the above reaction is CH CH, I I (a) CH —CH—cH, —cl @) CHy—FH— Cts a (©) CH —CH, —CH, —cl (@ CH,—CH—cH, —CHy a Which of the following will give five monochloro products, when allowed to react with Cl in presence of sun light (excluding stereoisomers) ? (a) n-pentane (b) Iso-pentane _(¢) 2-methyl-pentane (4) 3-methyl pentane CH3 th CH CH; | uyhv | CH;— cae —CH; ———> CH;— 5 —CH, — 5 —CH; CHa CHs Br 2, Brome-2, 8,5 wimetyl pentane 6) What is the value of x (% yield of product)? (@) 18% (b) 82% © 90% (@) 60% What would be the product ratio x/y in the chlorination of propane if al the hydrogen were abstracted at equal rate? (Chis — GH, — Cha —F¢9CHls — CHa — CHa—Cl+ GH, — FHC, wo q 1 3 9 1 eS b) 3 io 5 OF ot wi How many dichloro products (including stereoisomers) will be formed when R-2-chloropentane reacts with Cl, in presence of UV radiation ? @5 6 . @7 @s- 1g pater (AD Product (A) is: 4 4 4 @ ©) ) @ 14 4 ‘CO.CH, (@) Meso compound (b) Racemic mixture (c) Diastereomers (a) Optically active ° I (NOH, C10, 5. Ph—CH,—C—oH ESO (4) Product (A) i @ Ph—Co,H (®) Ph—cH,—OH (© Ph—cH, oD Match the column I with column I and with column IIL Mono-chloro products Monochloro products Compound (excluding Gndluding stereoisomerism) stereoisomerism) @ 0) 1 ow) 1 | CH — GH — CHa — Hs ) @ 2 oo 3 City His CH qe ©) ah—c—c—chy fe 3 ” 5 CH; CH; (a| Cs —CH2 CHa —CHs | ogy 4 @ 6as. ORGANIC Chemistry for UTJEE oropentane aro Optically active di-chloro products (P) | A B Ss Optically active dichloro produets (@) ic + Optically active di-chloroproducts (R) -chloroburane oh ie s Q=Riss 8. Match the column I and I. Corn CesT) Reaction ‘Type of Reaction fey yoo ® Meso compound cH, &) @ Diastereomers CH © © Racemic Optically inactive due to absence @ ® of chiral centerHYDROCARBONS (ALKANES) 187 9. Match the column : Reaction Product F | Hy ey, & |_ (1) BD 5: THF ® BawCosT HH, Sb o Soa @ H Saar? | Hy | @ 1) BD,:THF @, - 2, | aya,co.t | @ | Sr : | @ _@angta_, ke | @eH,cO,P | 10. How many distinct monochlorinated products, (including stereoisomers) may be obtained when the alkane shown below is heated in the presence of Cl, ? @)1 (b) 2 ©3 @4 6 11. How many distinct monochlorinated products, (including stereoisomers) may be obtained when the alkane shown below is heated in the presence of Cl, ?188 12. Match the column : ORGANIC Chemistry for IIT-JEE a Number of Wurtz reaction dimerization product bs | (2) | CH, -Cl oe? o 5 | (b) | CH, ~Cl+CH, -CH, -a @ - | CH, ~Cl+CH, -CH, cl © i «© : | © | cts cts cts -l a> 3 H,C ~CH-CH =CH-cH, -cl (@) | «cH, -cHy- > (s) : cH, 13. wa CH,—CH,—CH,—CH, S-2-chloro hexane HYDROCARBONS (ALKANES) —2> 00. G9 =total number of di-chloro product 189 1, A-a;B-GC-b 2. A-b;B-¢C-a;D-GE 3 abe 10. 2 1. e 12. a-sb-ne-p:d-a 13. 9