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Hydrocarbons

this is about organic chemistry jee advanced

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29 views15 pages

Hydrocarbons

this is about organic chemistry jee advanced

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Gaurav Kumar
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© © All Rights Reserved
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R. K. MALIK'S NEWTON CLASSES JEE (MAIN & ADV.), MEDICAL + BOARD, NDA, IX & X Enjoys unparalleled reputation for best results in terms of percentage selection www.newtonclasses.net HYDROCARBONS |JEE ADVANCED PREVIOUS YEAR SOLVED PAPERS] JEE ADVANCED. Single Correct Answer Type 1. Marsh gas mainly contains 2CO ODS) CH aC FTIEE 1980) . The compound with the highest boiling point is pentane , n-Hexane € 2-Methyl butane. 22-Dimsthyl propane {CIT-JEE 1980) Which ofthe following will decolouris alkaline KMaO, solution? 2 CH, BCH, CCL. de Hy (UEIEE 1980) “The compounds 1, 2-butadiene has only sp-hybriized carbon atoms only sp*-hybrigizedearbon atoms only sp and sphybrodozed carbon atoms sp, sp" and sp-hybridized carbon atoms (UT JEE 1983) . When propyne treated with aqueous H;SO, in presence of Hg80,, the major products & propanall b. propyl hydrogen sulphate €. acetone 4. propanol (IE IEE 1983) ‘Which of the following compounds doesnot dissolve in cone. H,$0, even on Warming? a. Ethylene tb, Benzene fe Hexane by Aniline (FJEE 1983) Bacyer’s reagent is alkaline permanganate solution bs. acidified permanganate solution 6. neutral permanganate solution 4. aqueous bromine solution ‘Acidic hydrogen is present in a. ethyne ». ethene . benzene 4. ethane (UTE 1984) (UEJEE 1985) 1. The highest boiling point is expected for a. iso-butane by, n-octane © 2.2.3 @. n-butane tramethy] butane ). The number of structural and configurational isomers of a bromo compound, C;HsBr, formed by the addition of HBr to 2-pentyne respectively a. Vand? b. 2andd ce 4and2 d.2and4 (UIEJEE 1988) |. The compound which has one isopropyl group is a. 2,2,3,3 tetramethyl pentane b, 2,2 dimethyl pentane c. 2,2, 3trimethyl pentane 4. 2methyl pentane (HT.JEE 1989) . The CH bond distance is the longest in a GH, hGH, «GH, d GHB (UT-JEE 1989) followed by the treatment with aqueous NaOH gives a. oCres b, p-Cresol ©. 24Dihydrony toluene d. Benzoie acid 1. cyclohexane is in "boat form 1. cyclohexane is in “chat” form Office.: 606 , 6” Floor, Hariom Tower, Circular Road, Ranchi-1, Ph.: 0661-2682623, 9635608812, 8507613968 NEWTONCLASSES.NET 39 YEARS] (IE-JEE 1986) - Chlorination of toluene in the presence of light and beat © (IT-JEE 1990) 1. When cyclohexane is poured on water it floats, because R. K. MALIK’S NEWTON CLASSES ‘cyclohexane isin ‘crown’ form cyclohexane is less dense than water (IIT-JEE 1997) ‘The reacon CH,CH=CH_{)-OH wih HBr + cucunien,-¢)-o1 b. CHCH,CHBr_/ \_on \/ «. cxycapicr,_ Br a. cHc,cHer-( Br IT JEE 1998) In the compound CH, = CH~CHl,~CH,~C=CH, the C,~C, bond isof the ype . a spa b. sp?—sp? © sp—sp" @. sp? —sp! CIT-JEE 1999) . The prodact (6) obtained via orymereuration (HgSO, + HS0,) of I-butyne would be ° 1 Cliy-Cl,—C—cH, CHi,—Ci,—cH—cH, . CHy—CH,—CHO + HCHO 4. CH.—CH,—COOH + HCOOH GFEJEE 1999) Which one ofthe follwing alkenes wil reac fastest wth , under catalytic hydrogenation condition? x (IT-JEE 2000) 1. Hydrogenation ofthe adjoining compound inthe presence cof poisoned palladium catalyst gives iH me * < >a (IIT-JEE 2005) 39 YEARS] ) PREVIOUS YEAR CH ADVANCI Office.: 606 , 6" Floor, Hariom Tower, Circular Road, Ranchi, Ph. 0861-2662628, 9696608612, 8607619968, NEWTONCLASSES.NET [JEE ADVANCED PREVIOUS YEAR SOLVED PAPERS] A cn 28 Me the roc (ine ‘The values of Nand M are 33 kad = somes: Facial 4 Gomer produ) 66 64 (IIT-JEE 2006) |. CH, —CH = CH, + NOC P Wdentify adduct a CHy—CH—CH —b CHy—CH—CH, T a No cl e. CH,—CH, (UTE 2006) The reagents(s) forthe following conversion Be Us F HSH isfare ‘a, Alcoholic KOH b. Alcoholic KOH followed by NaNH; ‘e. Aqueous KOH followed by NaNH 4. Zs/CH,OH. (IT-JEE 2007) |. The number of eyelic structural as well as stereoisomers possible for a compound with the molecular formula CHiyis aq no ek 413 (IT-JEE 2008) ‘The synthesis of 3-octyne is achieved by adding @ ‘bromoalkane into a mixture of sodium amide and alkyne, ‘The bromoalkane and alkyne, resectively, are a, BrCH,CH,CH,CH,CH, and CH,CH,C = CH , BrCH,CH,CH, and CH,CH,CH,C = CH ¢. BrCH,CH,CH,CH,CH, and CHC 4. BrCH,CH,CH,CH, and CH,CH,C = CH (IT-JEE 2010) . The numberof optically active products obtained from the complete ezonolysis ofthe given compound is CH 8 1 HsC—cit= CH C—cH=c—E—CH=CH-CH a CH ba e2 a4 (ITE-JEE 2012) |. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown in the figure bAeh~e] am [ . am The correct order oftheir boiling point is a. >>I b. MI>>1 I> I>T a. > I> (IEE Advanced 2014) 5. In the following reaction, the major product is on cA en oa 4 Br om Hime AO we i cs os fe moAAB ane SO (JEE Advanced 2015) 2 Ta daepetaee apenas Capa sr alee, oO i FAC CH ° coe ; 3 om ict 39 YEARS] JE Advanced 2015) = ‘Multiple Correct Answer Type 1. Which one of following has the smallest heat of 7 hydrogenation per mole? a. L-butene ©. cit-2-butene b. crans-2-batene 1,3 butadiene (HEJEE 1993) >. Toluene when treated with Br./Fe gives p-bromotoluene as the major produet because the (CH,) group. a. is para-directing b. ismeta-directing ‘. activates the ring by hyperconjugation 4. deactivates the ring (IT-IEE 1999) 3. The correct statement(s) concerning the structures (E), ®),and (G) stare: nem Pep me wa ‘Hs ay CH ® ® 606 , 6” Floor, Hariom Tower, Circular Road, Ranchi-1, Ph.: 0651-2662623, 9836608812, 8507613968 NEWTONCLASSES.NET R. K. MALIK’S NEWTON CLASSES a. @), (®,and (G) are resonance structures. b. ®), (F, and ©), (G) are tautomers. €. (F) and (G) are geometrical isomers. 4. (F)and (G) are diastereomers. (IIT-JEE 2008) 4. Compound(s) that on hydrogenation product(s) optically inactive compound(s) is (are) H 7 He a ne, bey My ¥ H % anc om (IEE Advanced 2015) Linked Comprehension Type Passage 1: An acyclic hydrocarbon P, having molecular fo. mula CgHjq, gave acetone asthe only organi produt through the following sequence of reactions in which Q isan interme ite organic compound. (UE-IEE 2011) Cette oq ‘ao “DNabi fet Ghatact eto) we ‘CHS 1. The structure of compound Pis CH,CH,CH,CH,-C=C_H H,CH,C—C=C_CH,CH, HC we né HE, Wye Sc-cac=H ne The strctre of compound Qis wc. fH a. HSc-e—ciichy He - H oH CH HC wese-t—cr, BC i we OH HSc-c-Gi-ca, By on : 4. CH,CH,CH, CHCH,CH, Passage 2: Schemes 1 and 2 describe sequential transforma- tion of alkynes M and N. Consider only the major products formed in each step for both the schemes. EGRCA TT egtateno p= = Scheme-1 no yy Nat eqs (IEE Advanced 2014) - The product X is — Poe cHCH,9, cxciiso “The correct statement with respect to product Y is ‘a. Itgives apositive Tllens test andisa functional isomer of X 39 YEARS] i. It gives a positive Tollens test and is a geometrical 5 isomer’of X . It gives a positive iodoform test and is a functional isomer of X 4. It gives a positive iodoform test and is geometrical 2 isomer of X Matching Column Type 1. Match the compounds/ions in Column 1 with thet propertiesreactions in Column Il. (IIT JE: 2007) “Column 1 Column 1 (a) CQH,CHO i 4-dinitrophenylhydrazine (p) gives precipitate with 2,| < (©) CHC= CH _|(@) gives precipitate with ARNO, © ON (© is amucleophile @r (© is involved in cyanohydrin formation Office.: 606 , 6” Floor, Hariom Tower, Circular Road, Ranchi, Ph.; 0861-2662628, 9696608612, 8607619968, NEWTONCLASSES.NET [JEE ADVANCED PREVIOUS YEAR SOLVED PAPERS] 3 Assertion - Reasoning Type Read the following Statement 1 and Statement 2 and answer as per the options given below: 1 both assertion and reason are correct and reason is the correct explanation ofthe assertion 9. both assertion and reason are correct, but reason is nt the correct explanation of the assertion assertion is correct, but reason is incorrect. 4. assertion is incorrect, but reason is correct . Assertion: Addition of Br, to I-butene gives two optical Reason: The product contains one asymmetric carbon. (IT-JEE 1998) . Assertion: I-butene on reaction with HBr inthe presence ‘of a peroxide produces I-bromobutane. Reason: It involves the formation of a primary radical. (QIT-JEE 2000) Assertion: Dimethyl sulphide is commonly used forthe reduction of an ozonide of an alkene to get the carbonyl ‘compound. Reason: It reduces the ozonide giving water soluble dimethyl sulphoxide and exoess of i evaporates. (UT-JEE 2001) Assertion: Addition of bromine to trans-2-butene yields meso-2, 3-ibromo butane, Reason: Bromine addition to an alkene isan electrophilic addition (IT-JEE 2001) Fill in the blanks type L is more acidic (Ethane, Ethene, Eihyne). (IT-JEE 1981) . Acetylene is treated with excess sodium in liquid ammonia. The product is reacted with excess methyl iodide. The final product is, (IIT-JEE 1983) ‘The starting material for the manufacture of polyvinyl chloride is obtained by reacting HCI with (IT-JEE 1983) 1. The terminal carbon atom in 2-butene is (IT-JEE 1985) . The structure ofthe intermediate product formed by the oxidation of toluene with C1O, and acetic anhydride, ‘whose hydrolysis gives benzaldehyde, is... (IIT-JEE 1992) 3. Kolhe’s electrolysis of potassium succinate gives CO, and (IT-JEE 1993) . Addition of water to acetylenic compounds is catalyzed by and (IT-JEE 1993) . 1, butadiene with bromine in molar ratio generates predominantly __ (IT-JEE 1997) 1. The imeraction of elemental sulphur with Grignard reagent ives (IT-JEE 1993) 1. The bond dissociation energy needed to form the benzyl radical from toluene is than the formation of the ‘methyl radical from methane. (IT-JEE 1994) 11. Vinyl chloride on reaction with dimethyl copper gives (UNT-JEE 1997) ‘True / False Type 1. Moist ethylene can be dried by passing it through concentrated sulphuric acid, (IIT-JEE 1982) 2, Photobromination of 2-methy! propane gives a mixture of L-bromo-2-methyl propene and 2-bromo 2-methyl propane inthe ratio 9: 1 (IT-JEE 1985) . In benzene, carbon uses all the three p-orbitals for hybridisation, CIT-JEE 1987) ‘An electron-donating substituent in benzene orients the incoming electrophilic group tothe meta-position. (UT-JEE 1988) = Subjective Type 1 Piste sca Dg ot i el pst following cas. Ethene mixed with air is passed under pressure over a 2 silver catalyst at 250°C GIr-JEE 1981) = . One mole of hydrocarbon ‘A’ react with | mol of bromine & giving a dibromo compound, C3H Br “A’ on treatment with cold dilute alkaline potassium 2 permanganate solution forms a compound, CH, ,0;,On = ozonolysis, ‘A gives equimolar quantities of propanone = and ethanal. Dede the structral formula ofA". ((IT-JEE 1981 9 line the reaction equence forthe conversion of eene to ethyne (the number of steps should not be more than two). CUTEE 1981) Given reason fr the following in one or two sentences (IT-JEE 1983) 1. Methane does not react wih chlorine inthe dark = I. Propene reacts with HBr to give isopropyl bromide tut doesnot give n-propyl bromide z ’. Give reason for the following in one or two sentences : * CUT-EE 1985) £ “Although benzene highly wnsetursed, normally it doesnot ndergo sion reaction z Following statement is true, only under some speci conditions Write the condition fr each sub question not moe than two sentences IE-JEE 1984 1. 2-methylpropene can be converted into isobutyl bromide by hydrogen bromide. fi Ethyne and its derivatives wll give white precipitate 2 with ammonica iver nitrate solution : Give the chemical test to distinguish between 2-buryne and L-butyne. UT-JEE 1985) How would you convert acetylene to acetone? UEJEE 1985) How many sigma- and pi-bonds are present ina benzene molecule? (IT-JEE 1985) Wate down the main product ofthe following reaction: Benzene —S!CtCOcuAtey (IT-JEE 1985) 606 , 6” Floor, Hariom Tower, Circular Road, Ranc! 4, Ph.; 0651-2662623, 9836608812, 8507613968 NEWTONCLASSES.NET R. K. MALIK’S NEWTON CLASSES 1. A white precipitate was formed slowly when silver nitrate was added to compound A with molecular formila (CH,,Cl. Compound A on treatment with two alcoholic potassium hydroxide gave # mixture of two isomeric alkenes B and C, having formula C,H», The mixture of (B) and (C), on ozonolysis, furnished four compounds: (UT-JEE 1986) i. CH,CHO. Wy. CH,—CH—CHO T CH,CHO ill. CH,COCH, cH, ‘What are the structures of A, B and C. 12, Answer the following with 2 suitable equation wherever necessary. (IT-JEE 1987) How can you prepare benzene from lime? fi, How will you conver toluene to m-nitrobenzoie acid? 13, Give a chemical test and the reagents used to distinguish ‘between cyclohexane and cyclohexene. (IIT-JEE 1988) 14, Write the balanced chemical equation forthe following: (IT-JEE 1991) “Ethylene glyco! is obtained by the reaction of ethylene ‘with potassium permanganate.” 15. Give reasons in two or three sentences only for the following: (IT-JEE 1992) “Phenyl group is known to exert negative inductive effect, but each phenyl ring in biphenyl (C,H, ~ CyHs) is more reactive than benzene towards electrophilic substitution’. 16, Write structure of the major organic product expected from the following reaction: (UT-JEE 1992) oO +(CH,),CHCH, CLAS 17. Give the structures of A, B and C (explanation are not required): (IT-JEE 1993) {A (C,H) which adds on FEB in the presence and in the absence of peroxide o give same product, C,H,Br. B (C,Hy) which when treated with H,O/H,SO, gives ‘CHO which cannot be resolved into optical isomers. . C(GH,.) an optically active hydrocarbon which on catalytic hydrogenation gives an optically inactive compound C,H 18 When gas A is passed through dry KOH at low temperature, a deep red coloured compound B and a gas are obtained, The gas A, on reaction with but-2-ene, followed by treatment with Zn/H0 yields acetaldehyde. Identify A, B and C. (UT-JEE 1994) 19. An organic compound E (C,H) on hydrogenation gives ‘compound F (C,H,;). Compound E on ozonolysis gives. formaldehyde and 2-ketopropanal. Deduce the structure ‘of compound E. CIT-JEE 1995) 20, Give the structure of the major organic products from 3-ethyl-2-pentene under each of the following reaction conditions: (IIT-JEE 1996) a 5. Give reason for the following: a, HBr in the presence of peroxide b, BrJH.O e. Hg(OAo)JH.0, NaBH, An alkyl halide, X. of formula C,H, Clon treatment with potassium tertiary butoxide gives 1wo isomeric alkenes ¥ land Z, (CH). Both alkenes on hydrogenation gives 2, 3-dimethyl butane, Predict the structures of X, Y and Z. (IIT-JEE 1996) . Complete the following, giving the structures of the principal organic product: (IT-JEE 1997) . The hydrocarbon A, adds one mole of hydrogen in the presence of a platinum catalyst to form n-hexane. When Ais oxidized vigorously with KMnO,,,a single carboxylic ‘cid, containing thee carton atoms, is isolated. Give the structure of A and explain. (UEJEE 1997) Give reasons forthe following in one or two sentences: (UTE 1998) 39 YEARS] “The central carbon-carbon bond in 1, 3-butadiene is = shorter than that of n-butane”. Complete the following reaction with appropriate structures of products/reagents: (IT-JEE 1998) C.H,CH=CH, —*2-4[A} eS (IIT-JEE 2000) CH, = CH” is more basic than HC=C”. What would be the major product in the following reaction? (IE-JEE 2000) i on Hy Give reasons forthe following: (UEJEE 2000) I tertiary-Butylbenzene does not give benzoic acid on ‘treatment with acidic KMnO,. i, Normally benzene gives electrophilic substitution reaction rather than electrophilic addition reaction although it has a double bond 2. Monomer (A) ofa polymer on ozonolysis yields two moles ‘of HCHO and one mote of CH;COCHO, a. Deduce the stricture of (A). 1. Write the structure of “all eis" form of polymer of compound A. (IE-JEE 2005) . w observed = ZnX; where, jis the dipole moment of the suble conformer, and X, isthe mole fraction of that conformer. ‘a, Write the stable conformer for (Z ~ CH, ~ CH, ~Z) in Nowman’s projection. If Houson = 1.0 D and mole fraction ofthe antiform = (0.82, find the j_ gauche form, Office.: 606 , 6” Floor, Hariom Tower, Circular Road, Ranchi, Ph.; 0861-2662628, 9696608612, 8607619968, NEWTONCLASSES.NET ) PREVIOUS YEAR CH ADVANCI JE [JEE ADVANCED PREVIOUS YEAR SOLVED PAPERS] z cupy 31, What is the total number of cyclic structural as well a5 . Write the most stable meso conformer of | stereoisomers possible for a compound with the molecular cHDY formula CH? (IF. JEE 2009) If (Y= CH, about C, ~C, rotation and (i) ¥ = OH, about CC; rotation (IT-JEE 2005) ANSWER KEY JEE Advanced Multiple Correct Answers Type Ld Bay: 3. bead. Single Correct Answer Type 4 bd, 1 6. Ta. 7 . Linked Comprehension Type 1 Lo 7 Ld 2b Ba 16, 2a. 26. . i 31. . . _ Assertion-Reasoning Type 36. ba Be da ‘True(False Type 1, Fale 2. True 3. False 4, False Matching Cotumn Type 1. &9p,4,5,b34,¢-9 que 39 YEARS} Ee SCT eran aa ne TON Va Shand 606 , 6” Floor, Hariom Tower, Circular Road, Ranchi-1, Ph.: 0651-2662623, 9836608812, 8507613968 NEWTONCLASSES.NET R. K. MALIK’S NEWTON CLASSES HINTS AND SOLUTIONS JEE ADVANCED Single Correct Answer Type 16d. By the decay of plants or animals prescat in wet or spongy land (aed swamps oc marsh) and by the action of bacteria on them, methane pus is product. Because ofthis method of formation, methane gsi aso called marsh gs ‘With the increase in C atoms and decrease in branching (or staight chain), tbe boiling points of alka-nes increas. So, ‘serane asthe highest bling pont .Alkenes and alkynes decolouise alkaline KMnO, solution (GBaeyers tes for unsaturation. > CH,—C=CH+H,0— "SHO. cH, —C-=cH, —cH,—c—cH, rl ° CHty= CH, + 50, CHyCH,OS04H Cie + F504 GHSO4HC+ HO Gale HeS0, > No reaction GHB +H,50,> Cay NHSOG Only hexane doesnot dso in cone. H,S0,exen.on warm ing ‘Alkaline permanganate soltion sown os Hacyers regent cH, oN Na i Hw GH fue ce (This reaction indicates the presence of sic hyérogen in ethyne) Alay thessmenumbrofCatoms n-Octanesastaghi-hain compound that as a age suri area. S, tee ar mor van der Waal foes faction eating ns high tone pint 1 and I are structural isomer; I and I Mand IV are dastereo- ‘mers (o four configuration isomer}. 1d. 2th Peni (Gi Gicth,—~chh-cHt oie 12.¢. CH bond distance isthe longest in alkane (CH). cen ert Hs ccly & As alkenes and eycloalkanes are non-polar molecules and are insoluble in H,0, they are also denser than H,O and thats why they can oat on water. 15.0, The reaction of CH—CHi==c—(_)—OH with HBr is ven as follows: Br ‘The mechanism ofthe reactions is represented as follows: cur didcr()-o1 sao en-enin {pon setae ccn,—cn¢_)-on Fae? CHCH—C Br Hence, C; and C, are 17.8, CH,—CH—C=cH 2 CHty-CH C= cH Coc e—cH, * (fm) Because keto form is more stable than enol 18.2, Stability of alkene se ————_t_ Heat of hydrogenation Hence, reatvty of alkene = heat of hydrogenation of alkenes Tn these, cisalkene are more reactive because of greater strain & Initby poral hydrogenation of —C=C, alkene is formed. 20, ¢. In the presence of peroxide, HCI and HI react with alkene as follows Firat step a R-Q-9-R—*92R-0" ) PREVIOUS YEAR CH ADVANC JE Office.: 606 , 6” Floor, Hariom Tower, Circular Road, Ranchi, Ph.; 0861-2662628, 9696608612, 8607619968, NEWTONCLASSES.NET [JEE ADVANCED PREVIOUS YEAR SOLVED PAPERS] b. RO'+H-X+ ROH Xt Second tp RICH=CH, + X* > R'CHCH,X + R'CHOXNCH, enstaxox? For HCL, step 1) is eadothemsc and step Is exaheri, wile for Hl tp (6) is exobemie and ep T's endothe: mic: Hence, each case, one ofthe steps is exothermic, de to this reason HCl and HI do aot sve an Markvnikows ad tion to skenes In butyne-I, acidic hydogen is present while in butye-2 acidic hydeogen is ot preset 0 Buy gives ed pp. ith ammonical Cu, solutions, while buyne-? does not give these pe (CH—CH, —C=CH + Cu,C1, + 2NHLOH > ere 2C1—CH, —C=C—0u | «201,01 +2840 CH—C=C_CH + C101, + 2NH,OH > No reaction i nl ann al th as en Pt een itraetee 3 Sliced penis F ” cats yrs otapiet pat fete rep ease oe mbps along a itty rennin as hong Meera Se ome fe die tase ncn fy as Coosa ey nape per ope Mechanism: 2 pen pa On os : i cH ote, cH-C-cHy HyC-C-cHs =O= 6 on 25.9, 2-hexyne gives trane-2-herene on treatment LifNH CHC —CH Cac, +, EI, 4 cH,-CH.—CH,-C=C—CH, 5 26.) On chlorination of - meth butane a oa Fou chiral compounds are formes. 27.c. (C-Br) bond is weaker than (C-CD bond: hence Wurtz reaction will take place with (C-BE) bon. oSOta 1 RES com ms Opa ane a>) Fraction distillation separates structural isomers and poomett ¢al isomer | D.U..,t optical isomers. So, the value of Mis CH=CH tty+NOCIS Cy= CH CH, 4 This ractn an ccnp fcc ston exon scot poe eal dlorstetsie Nteaentiornane (Megatv ut of aive og ass byaopomede carina pds baa espana caaten Tsao epesntdia fom of lowing mechani Step. NOCI= NO” + cr tiga” nae Step IL CH,—CH“CH, + NO* CH CHC oc ey Step I. CHy-CH-CH, + C= cHy—cH—etty No G. No "al pre Mb Beng, SOKOH py yw HB = Office.: 606 , 6" Floor, Hariom Tower, Circular Road, Ranchi-1, Ph. 0861-2662623, 9636608612, 8507613968, NEWTONCLASSES.NET 39 YEARS] ADVANCI JE R. K. MALIK’S NEWTON CLASSES 0 31. a. CsHig= IDU. Itcan be eyeic and canbe alkene. a 7 Ae Oras or @ Hc | cH A HOH HE (einandoptesty (nan nd ope © ® ‘Therefore, toa cylic and stereoisomers =7 oor Mei Me es &y a ® ® rssh ANIA oe TY |sane wav] ® i? << aGn sessed ee ‘Total numberof eyli,acyelic and stereoisomers is 13. How- ver inthe problem only eyeic structural andsteroisomers ave been asked. So the total number of isomers would he seven IR + NaX ien.Cr.crave Hi Br (MeCH,C == CH + BrCH;CH,CHMe = CCHCH:CHMe Mib, As branching increases surface area decreses so boi decreases, 50 order of boiling point is I> > L Cis ch, dD Le HB yo POF Ic — AW? ou indepen ar Tigh Pesos ple Correct Answers Type 1, 3-butadiene shows smallest heat of hydrogenation due to is 2 higher stability (which is due o resonance ) ‘Trans-D-tene is more stable than cis--butene on the basi of| heat of hydrogenation. ‘bute is es stable than 2-butene du to hyperconjugation (CHy—CH = CH= CH, (Shows six no-bond resonating struc- tures) While, I-butene due to hyperoconjugation shows two no- Z bond resonating structures. (Resonance is more powerful than bhyperconjugstion) Order of stability 1, 3-butdiene > zrans-2-butene> c-2-butone > I-butene Heat of hydrogenation batene > cis-2-butene > rans-2-butene >I, 3-utadiene CH Cis “Oo “The CH) oup sabe wo activate the benzene ing by hyper conjugation. So, (-CH,) group shows o/p-directing influence ‘on the benzene ring. byevd. Option) is wrong asin esonance toms donot loose their position ‘They ae keto eno attomers and G are cs rans isomers agg en ey ec csi, (Opgaty sce er 39 YEARS] ) PREVIOUS YEAR CH ADVANCI JE Office.: 606 , 6” Floor, Hariom Tower, Circular Road, Ranchi, Ph.; 0861-2662628, 9696608612, 8607619968, NEWTONCLASSES.NET [JEE ADVANCED PREVIOUS YEAR SOLVED PAPERS] Linked Comprehension Type 1.(0,2.(6) a cmuseon Hic Nevo Seater -=eor-cion Haneef aon Matching Column Type 1. @ 1.4.50) 90: FORO IQ (ote: Assuming AgNO, is ammonica) No; a PHCHO + 0,\{O NHN, on 7 > PhHEN—NH—{O)—NO PRCHO+ Ag,0—Ms PRCOO+ AB cn i Paco ph—C—0 1 a b. CH,CaCH AO. cH, —CaC“Ag'L cN . PhCHOES Pho 1 H ABNO, +CN~—> ABCN 4. AgNO, +P > AgtL Assertion - Reasoning Type 1a CH,—CH,—CH=CH, + Br > crc —ta—cs ‘duet one chiral earbon Bi Bs Bh asseron and reason are comet, and reeson isthe correct explanation ofthe assertion, Assertion is comet but reason is incorect because I-butene ‘on reaction with HBr inthe presence of a peroxide produces ‘bromobutane. In this reaction, secondary free radical is formed as intermediate product is formed. La. (C.H,CO),0,->2C,H,COO" b, CH,CO0"+ HBr C,H,COOH + Br° 1H, + Br» CH, CH, ~CH-CH,Be i cH,-cH,~cH i. CH,-CH,-CH-CH,Br+H-Br -+CH,—CH,~ CH, ~CH,Be+ Br" 9. Assertion and reason both are comect and reson isthe correct explanation ofthe assertion, ‘Assertion is comet but Reasonis not the correct explanation of the Assertion addition of Br to trans-2-batene is foie, while itis anelecwophilic addition in alkenes) Fill In The Blanks Type 1. Eihyne 2. 2-butyne CH=CH +Na—8™5. cH =cNi SSH Nas Na 284 CHC =C—CH, HC=CH+HC1—+CH,=CHCI sp: HjC- CH=CH -CH,, C.HigCH(OCOCH,), (benz diacetate or benzyidene acetate). ethylene cHCooK +2140. CcHCOOK cu mem OH Bein. Ys aco3 +280 + mete H,S0,.H80, 208 dil H,S0, and 14 Hg50, 3, 4ibomo--buene tow temperature) 1, adda at ow temperatre while 1 adduct at higher tem perature en te Team AA Office.: 606 , 6" Floor, Hariom Tower, Circular Road, Ranchi-1, Ph. 0861-2662623, 9636608612, 8507613968, NEWTONCLASSES.NET ) PREVIOUS YEAR CH ADVANCI JE R. K. MALIK’S NEWTON CLASSES 9. thiol 10. less 1 propene Cll, = CH-C1+ (CH,),Cu-+ CH, = CH-CH, +CH,CuCL ‘True / False Type 1. False: Ethylene on reetion with sulphuric acid gives ethyl hhydrogen sulphate. Thus, moist ethylene canbe dried by PO, ‘Tre: as there are 9, 1H and 1, 3°H. False:In beazene, cach carbon atom is sp-hybridised hence, carbon uses only two p-obials for hybridisation, False: An electron-donating substivent in benzene orients the incoming elecwophile to the orho-and para: positions ‘Subjective Type Eahylen oxide ee] ae Oxirane a 228s Hs Br om neal Methane doesnot reat with chlorine inthe dark because chlorination i fe aie substitution and fice radials are produced i presence of light Iisaccordace with Makoviko’s ule which rds the sublty of secondary carbon on oer primary carbonium (CH,~CH=CH + HBr CH,—CHBr—CH, 5, ln benzeu, al he thes fond are load anit is reso- ance stabilised, hence it does no undergo addon reaction I ic undergoes aditon the ts somatic characteris ost 6 Under norma condition, fr-bly! bromide is formed isobutyl bromide is formed in presence of peroxide CH cH ose f Bitt,c-CH-CH, SG Hyc=C~CH, H+ Be > Hs Hite Hye—E—crh Br 1 Ettyne (HC=CH) and only those derivative which have at least one acetylenic hydrogen atom (=C—H) i. terminal alkynes wil give white preiptae with ammonical nitrate solution. 7. Butyne-t has acidic terminal H-atom and gives ared pp. with ammon- ical Cu,Cly. (CH, —CH,—C= CHS CH,CH,—C=C xu Buyne-2 {thas no termina acidic H-atom and doesnot give red pp. with sammonical CusC CHy—CaC—Chty S59 Nope. Hm, . HC= CH 2 cH CHO —1.cH,COOH sie 222% (CH,C00),ca—= 3 CH,CocH, 4 gag al oo, HX H Hence, ¢-honds = 12 bonds = 3 Its Friedel Crafts acylation. cox, Bensese Nt ty piel 1. A cn ration with alcohlis KOH gives a mixture of two isomeric alenes Band CH C1 EB Ct Cas Mistre of 8 and Com ozonolysis gives four products, (1) CH,CHO @) C,Hi,cHO on aychycoct, Sonn cy Since Band Careof sx caton toms each nth poet fermen oroolyss foreach alene mast cotain ial i carbon ats. That is why one alten gs cx,cHo + S>cH—cHo awe and ter see ines CjCHO and CH,COCH, Ths alkene ae Ch, ccc, chy a cH Alls CH CHC: a Sous Office.: 606 , 6” Floor, Hariom Tower, Circular Road, Ranchi, Ph.; 0861-2662628, 9696608612, 8607619968, NEWTONCLASSES.NET PREVIOUS YEAR CHAPTERWISE SOLVED PAP JEE ADVANC [JEE ADVANCED PREVIOUS YEAR SOLVED PAPERS] 1B Sine nd Cred om hie Atha shoad ts ot SScH-CH—CH,—CHy cH” I d acon ind as cH ‘KOH (ale) Ser-gi-en-cn, 2 arf & on, om, Secaci-cHs—cHs + N\ C-CH=Cit-—CHs cy” crn Lime is heated with coke at high temperature and hen tydroysed to form acetylene, Tis acetylene 08 pass through aed ube poyerzs wo form benzene. 10+ 3¢ BE cacy +cot CiC, 424,04 GH, +C4OH), ca SF ecu of Eee tf cH Coon, sai coon i 6 a oO Newion Ox, ‘Toluene Benzoic cid m-Nitvo benzoic acid Cyclohexene decolourise the pink colour of Baeyer’s reagent, while eyelohexane does not respond 1 these reagents. oon a +1H0+0) HEAL HMO, io on ‘cH, 41,0 +2KMn0,+CHj=CH,) 93) | CH,OH +2Mn0,+2KOH In biphenyl, one phenyl group acts as an electron donor, while the other acts as an electron acceptor. Thus, due to this eason, the phenyl ring i more reactive than benzene toward elect iii substitution, Cih_CH—CHACL+ Ac, + HCG FANE oy by amp gu, 12 ° Oot ou [SE reaction takes place at3°C*] 17. LA (CAH) ads on HBr in the presence and in the absence ‘of peroxide wo give same product, HBr hence, (A) C,H ‘must be symmetrical alkene A= CH,—CH=CHACH, on 1 CH,— CH=CH, +#,0—52.4.cH, Cc, 1 i cH cH, ety ces seawdecn c=cH,—CH,— CH —cH=cH, 1 cH, aan pean CH, —CH,—CH— cH. 1 oy enily cS Gn He, cx, i oy ec crn er, sac cH Hence, gas Ais ozone because in above reaction, ozonolysis of ‘butane? takes place. Gus A+KOH(y)—> Bc Peay” ae *) 40,+4KOH —+ 4KO, +2H,0 +0, Azoroe 0) 1 = Posi oid (KO,) Comoimt— CoOngsn 03 (Cats pte Cale [mn HCHO + CH;—C—CHO- 8 Thus, Compound Compound errata ence, compound E must be diene. So, its possible structure given as below: —sssos 2cH,0 + CH, —C—CHO = i alto, 4 Thus, compound CH= C— CH=CH, is E Hi cH Office.: 606 , 6" Floor, Hariom Tower, Circular Road, Ranchi-1, Ph. 0861-2662623, 9636608612, 8507613968, NEWTONCLASSES.NET 39 YEARS] ) PREVIOUS YEAR CH ADVANCI JE R. K. MALIK'S NEWTON CLASSES Compound CH, — CH—CH,—CH, is F i cH 1b CH,—CH,—C=CH—CH, +B, 25 1 city outpe ec, Gots 2 Sty en & CH,—CH,—C=CHcH, ONO, i cl 0 -a1-t gon Cats HatA0 antl Noy ou cH, ba >in penne bt a. x SME, y+ Z Allyalide => Alene, general cormul CH, CH lamers cHcH, rt Y o-Zom hydrogenstion gives CH, —C—C—cH, vt HoH cucu, rt . > Xis cH, -C—C-cH, i aH cH cH Hye = Cc) + c= CH CH coe cH H y Zz 22, Itisan example of elimination (Proceed via carbene) aa meno 82 | 23, 4. should bean alkene as it adds one mole of H, The Cy alkene shouldbe symmetrical ecause on oxidation it gives a single carboxylic acid having tee carbon atoms. (CH,(CH,),CH, —CH,CH,CH-CHCH,CH, = 2-9 208,CH, C008 2, 1, Studien shows the rope of esonance afer cn tu. Greco Sotond between siond and thin C-atom show peial double bond character. Hence, bond length is shorted than C—C bond ‘in n-butane (due to presence of ressonance) cic Car Osos w om a oa crs CCH, = CH is more basic than HC=C~ because electronegativ- ity of of HC= C”is higher in comparison to such carbon of. CHy=cHr, InH_-C=C-,C.atomis sp hybrid whi is sp-ybrd. Soin C-atom of HC = C s-otbital character (S0%) is higher than that of CH, = CH” (33.3%) On the bass of atraction of eleton in orbital > p>d>f,the electron atracton tendency of such C-atom of HC = C”ishigher than that of CH, = CH. So rate of donation of pair of electon in CH, = CH" is higher than tha of HC = C~ beeause basic strength is directly propor tional wo rate of donation of fee pair of electron, Hence dv to above reason CH, = CH” is more basic than HC Cc. 7. In presence of Lindlr's catalyst (Pd and CaCO in quinoline) patil hydrogenation takes place and to give cis fsomer and Lindla's catalyst convers (C=C) to ( crx Xs ALPS t cH 1. In ehutyl benzone, the C atom ofthe butyl group doesnot have H atom (benzylic). 1. In the typical reaction of benzene, the relectron of the benzene ring serves asa source of electrons for electrophilic reagents. Benzene doesnot show adition rections a5 the case of alkenes, but undergoes substitution reations ‘which hydrogen atm attached tothe C atom is replaced by mother atom of group of atoms in the form of H®, ie, ives elecirophli substitution rections. ant (ae o GS S: Office.: 606 , 6” Floor, Hariom Tower, Circular Road, Ranchi, Ph.; 0861-2662628, 9696608612, 8607619968, NEWTONCLASSES.NET ) PREVIOUS YEAR CH ADVANCI JE [JEE ADVANCED PREVIOUS YEAR SOLVED PAPERS] cus ebmerinioe by, — a ro ae ars z z He eS z 4 ron (caste os Mole tation of nfonn = 0.82 Mole action of gauche form = ~0.82) =0.18 Mn = 10D oe ak 10 want) %082 + pgs) X018 fan) =0 (ro Newnan’ potion wo etre tod al H ectos cance) 1.0 = 082+ pigauche) «0.18 igmede)= 12-555 ot cH ntsform i a stale conformer. (i), gauche form is a stable conformer due to the intramolecular H-bonding DL. for C3H,y is one (one ring or one double bond) but only cyclic stricture with stereoisomers has 1 be answered. The possiblities are: Me Me v4 © Rw Me O10 Enantomers trans (OA) ‘Total numberof cyclic isomer and stereoisomers is seven, Office.: 606 , 6" Floor, Hariom Tower, Circular Road, Ranchi-1, Ph. 0861-2662623, 9636608612, 8507613968, NEWTONCLASSES.NET ) PREVIOUS YEAR CH ADVANCI JE

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