JEE abv ORGANIC CHEMISTRY PART-I(Jr)_JEE ADV IMPORTANT QUESTIONS a NARAYANA IIT-JEE ACADEMY - INDI NARAYANA GRABS THE LION’S SHARE IN JEE-ADV.2022 EXCELLENCE IS OUR TRADITION 3402 RANKS OVERALL! eerie ed ‘JEE-MAIN 2022 Page |1if) _JEE ADV IMPORTANT QUESTIONS JEE abv ORGANIC CHEMISTRY PART- SINGLE CORRECT QUESTIONS oe CH,-CH. CH, +2NaCl Then ¥,¥ and Z includes A) Sodium ethanoate, ethane and ethyl chloride B) Sodiumproponoate, ethane and methyl chloride C) Sodium butanoate, ethane and ethyl chloride D) Sodium propanoate, ethane and ethyl chloride Ch, qs CH, ~CH, ~CH ~CH, +Cl, > 2 4 Major product CH,-CI CH, 1H, a ie is cn, Hs CH, -CH, -CH - CH aaa CHG GH- CH, 4) cH, a a CH, CH, i qh cH, - ~cu,-cn,-b-cH, Poe we 4 -CH, 1 a H. a 0 CH, D) CH, 3. Which of the following halogenations reaction of alkanes is reversible? A)Bromination B) Chlorination C) Iodination —_—_D) Fluorination 4. In which of the following acid — base reaction takes place? CH.MgCl Brin water 40 ars A) B) a OOO ec Reactivity of hydrogen atoms attached to different carbon atoms in alkanes has the 5. order (towards electrophilic substitution reaction) A) Tertiary > Primary > secondary _B) Primary > Secondary > Tertiary C) Both (a) and (b) D) Tertiary > secondary > Primary @)NARAYANA ame I-JEE ACADEMY-INDIA Page |2JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 6. How many isomers [including stereo isomers] (of formula CsHoCl2) are obtained from the monochlorination of (S) ~ (+) ~ 1 - chloro -2 ~ methyl butane A) six B) five ©) two 7. The relative rate of extraction of H and D is 2.6 : 1. product A and B in the following reaction is: CHD, + Cl, + C,HD,Cl + C,H,D,Cl « & A) 27.8%, 72.2% B) 72.2%, 27.8% C) 56.52%, 43.48% D) 43.48%, 56.5 8. ayers ee Bao, MO, Low, LL, agent ZN Gmajor)2-RMEX (aaj) 3.0" compound D is OH ° ° R R R R A) © iB) ©) ct Dy cH Ae HBr 9 ame Major product at higher temperature Z Ag AY A B Ay Br B) Br Oo a r D) RAL 10. CH “H ~CH, ~CH, +(CH,),CCOCL—*-+P (Major ) CH, =CH —CH -CH, oe = A) v B) CH,-CH =CH -CH,-CI i CH, —CH -CH, -CH, ©) CH,=CH-CH,-CH,-Cl D) | | cl OC(CH,), 11. For the reaction of HC! with the following alkenes, predict the correct sequence of reactivity as measured by reaction rates (l) CICH=CH2 (II) (CHa}2C=CHa (II)OHCCH=CH2 (IV) (NC)2C=C(CN)2 4 | @)NARAYANA Sse | (OD) see ReabemeNoa Page |3JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS (A) IV>1> > (B) I> 1V> > IL (C)ll>>Iver (D) U>1>m1>1V 12, Identify ‘Z’ in the following reaction series, CH,CH=CH, —UEHMIFIMOUO oy) ALO, ey _HOR (2) gl OH OH 7 = : ve » + c ca a 7 a H x a Cc) D) Ho a 13, HC 2cH BGs, 4 ph, _ tans yp: Where Eis == A) B) BZ © D) 14, The number of alkynes with molecular formula C,H, is possible to produce metallic derivatives A)3 B)2 Ol D)O 15. The product of the following I and II sequence are related as (i HyPalcaco, (i) BryCCl, A) Diastereomers B) Identical © Enantiomers D) Geometrical isomers @) NARAYANA oat | IT-JEE ACADEMY-INDIA Page |4Jee abv ORGANIC CHEMISTRY PART. if) _JEE ADV IMPORTANT QUESTIONS 16. _ Inthe given reaction cna Br cH, E10) A, The products are 20% . A) 80% C=C-CH, Cor aod 20% B) 80%, , : A=C-CH, Cc) 100% D) 100% 17. Me~C=CH—sbetube_,(p) Which of the following in major product of the above reaction? CH, ° ei nC cH, cH. cH, ©) CH, a I-JEE ACADEMY-INDIA CH, B) cH, D) CH, cH, Page |5JEE abv ORGANIC CHEMISTRY PART- 18, 19, 20, if) _JEE ADV IMPORTANT QUESTIONS Which is the most suitable reagent among the following to distinguish compound (II1) from the rest of the compounds we, i) 5 He iv) ae A) Br, in CCl, B) cold aq Alk. KMnOg C) Ammonical AgNO3 solution D) Alllof these Propyne and propene can be distinguished by A) Cone. 1,50, B) Brin CCT, C)dil. Kno, D) AgNO, in ammonia An optically inactive hydrocarbon [A] of formula C8H12 on reaction with 1 equivalent of H2/Pd gives racemic [B] of formula C8H14. [A] reacts with ethylene at 150°C to give and optically inactive hydrocarbon [C] of formula C10H16, Reaction of [A] with NBS/light gives [D] with the formula C8H1IBr as a racemic mixture along with an achiral compound. Compound [A] is a 8) f () Ce (D) ( SS CH =CH esi 40H, tates __*8" 1) Regarding ‘D” the wrong statement is A) Hybridization of carbons is ¥* B) It is useful for the preparation of mustard gas C) It gives Baeyer’s test D) It mainly participates in substitution reactions @) NARAYANA oat | IT-JEE ACADEMY-INDIA Page |6JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 22. Two CsHs isomers undergo catalytic (Pt) hydrogenation to form the same CsHio product. On ozonolysis followed by oxidative work up (H20:), one isomer gave a CHO. diacid, while the other isomer gave a CsHsOs ketoacid. Which of the following isomeric pairs correspond to this evidence ? A) Cyclopentene and 1 — pentene B) cyclopentene and 1 — methy! cyclobutene ©) 1 ~ methyleyclobutene and 3 ~ methylcyclobutene D) cyclopentene and 3 - methylcyclobutene 23. Which of the product is obtained in the following reaction oa, me product OH, 120, 24. 6 CH, ~CH, ~CI— 24> A> pS >, Possible isomeric monochloro products A)3 B)7 Os D)6 25. ie i i) 0. (ss prsauetds The Products formed are LZ (#) 2,0 CH, Z if A B i c D) Both (A) and (B ) Cty-C- coon 3) HOOC-cooH C) Clis-C-C-City ) Both (A) and (B) NARAYANA ru IT-JEE ACADEMY-INDIA Page |7JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 26. In which of the following case. the rate of Electrophilic Aromatic Substitution will be faster. Hy cs i cl ey se A) OQ B) A o —_ D) Sy 2 2 | 2 I _ 27. Increasing order of rate of reaction with HNO3/H2SOyj is: I IL ll A)MI(ii)>(iii)>(iv), B) (iv)>(i)>(i)> (ii) ©) Gii>Gii)>Gv)>@) D) (ii)>()>(iv)> (iii) 30. The electrophile which is considered to be the active agent in the nitration of benzene is A) NO; B) No ©) vO! D) HNO! @) NARAYANA oat | IT-JEE ACADEMY-INDIA Page |8JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 31, The conversion CHC CH;CHCH, Br Can be best effected using A)Br,/CCI, B) Br, /H,0 O)Br,/ Fe D) Br, / Benzoyl peroxide 32. 1 mole of 50% pure CaC,on hydrolysis followed by passing through red hot copper tube, how many moles of Benzene is formed 1 4 1 1 Ay = B) = QO-=- D = dS DA dee § 33. _A Friedel-Crafts reaction of excess benzene with chloroform produces cl Cs I I A) C.HCHCL BY Cis CCl C) C,H,-C-C,H, D) allof these I H H 34. The major product obtained in the reaction : © ah. » 66) » O1+.0)-—- . Ot, 4 O-- 6) (A) ®) © @) (a) B) © ©) @) NARAYANA oat | IT-JEE ACADEMY-INDIA Page |9if) _JEE ADV IMPORTANT QUESTIONS JEE abv ORGANIC CHEMISTRY PART- cH KMnO, HNO, | coneHSO, |» 4 —_ (Major Product) 35 the product B is B) 3-Nitrotoluene A) 3-Nitorbenzoic acid D) 4-Nitrobenzoic acid ) 4-Nitrotoluene ‘The product formed in maximum proportion in the following reaction is 36, cH c11,cn cyan A ep CH{CH;CH3 OF C cr ,CH,CH CH; sil) 7 CH; 37. Chlorination of Toluene with an excess of C iS in the presence of light and heat gives product (X) . the compound (X) is heated with Aqueous NaH and finally acidified to give a compound (Y). Y is a, . cH 7 om yy © » or Page |10JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 38, 40. 4 OH LNaOH ti. 2.CH30S0,0CHs cl oH on HOS 6 cH,0,8. cl ) cl on OcHy HC, cl Which of the following will have fastest rate of reaction with Br, / FeBr,? oO Oo. The major product formed in this reaction is (cH,), CCH,CL-8> CH,C(CH,), C(CH,), CH,CH, yo ye CH(CH, )CH(CH,), CH(CH,)CH,CH,CH, oS men Which of the following compounds has most acidic hydrogen ? Ore eS iD SH 2) SH c R ! C) x 7 Lo 3) CLéy 4) N i R ) © ©) 4 OCH, ¢ \ ¢ @) NARAYANA IT-JEE ACADEMY-INDIA Page | 11JEE abv ORGANIC CHEMISTRY PART- af ff Excess A What is the product of above reaction from following option (A) we rx) (B) O-) br © {OF a{O) Br (@) “60 Br 43. The major product formed in the following reaction is: H ese wSPh u oH "OH sph t sPh VA. 90H “OH *SPh A 44. Consider the epoxydation of cis-butene with peroxy benzoicacid which statement describes the stereochemical out come of the reaction? A) Cis-1,2 dimethyloxirane, mostly as (s,s) enantiomers B) Cis-1,2 dimethyloxirane, mostly (R,S) enantioners i) NARAYANA IT-JEE ACADEMY-INDIA Page | 12 if) _JEE ADV IMPORTANT QUESTIONSJEE abv ORGANIC CHEMISTRY PART- 45. 46. 47. 48. if) _JEE ADV IMPORTANT QUESTIONS C) Cis-1,2-dimethyloxirane, a racemate D) Cis-1,2-dimethyl oxirane, a meso compound The reaction sequence = CH =CH, 12H will yield A) A pair of products that are enantiomers B) A single product that is optically active C) A pair of products that are diastereomers D) A Meso compound TUPAC name of the following compound is, CONH2 COCH3 (A) 5-acetyleyclopent-2-ene-|-carboxamide (© 1-(2-carbamoyleyelopent-3-enyl)ethan-1-one (D) 5-acetyleyelopent-2-en-1-carboxamide ‘The C -H bond having the lowest dissociation energy is (A) PhERC - (B) HsC=CH - CH: (© MeHC =H (D) MexC - H MULTI CORRECT QUESTIONS Which of the following hydrocarbons give dl-pair on catalytic hydrogenation to alkanes? A yee ® An KS (© He, Hse, o) 8 cits yi nyc 2 ? CHy nd ch, fi @) NARAYANA oat | IT-JEE ACADEMY-INDIA Page | 13JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 49. Which of the following hydrocarbons give dl-pair on catalytic hydrogenation to alkanes? SS wet Aye B) Meee sic oh Me je 9 Gs D) Me 50, Which of the following reactions will give Alkane as major product? Cl testers ae (eae mh = a ea as = 2 ust 51, An alkene on reduetive ozonolysis yields only ethanal, The other isomer(s) of this alkene which on reductive ozonolysis may give (A) propanal (B) methanal (C) propanone () isobutanal 52. The alkynes CHs-CH (A) Tollen’s Reagent (B) Ammoniacal Cu:Ch solution H and CHs-C=C-CH, ean be distinguished by the following (©) Fehling’s solution (D) Baeyer’s reagent 53, Which of the following are obtained as the only product after hydration of suitable alkyne with HySOy, and HgSO,? ° A ° AS a! oT A) BR ons ° Q 54, Which of the following reaction will be useful for conversion of P, to P, A) Clemmenson’s reduction B) Oppenauer oxidation ©) Meerwin Pondorff verely reduction _D) Tischenko reaction ); NARAYANA oat | IT-JEE ACADEMY-INDIA Page | 14JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 35, 56, a 58. Which of the following reaction(s) give(s) aromatic compound as product? 7 2AgBF, ‘Br A) @ K (Metal) B) CH ° D) Cans 5 products: cH ‘The products formed are t ih (A) CH,-C-CHO (B)CHO—CHO (©) CH,~C-C-cH, (D) HCOOH Which of the following groups cannot participate in resonance with benzene ring? CH (A)}—COCl ®) —Nis o- oO Which of the following compound(s) is/are more reactive than benzene towards nitration? COOH CH; OH HsC. CH, (A) (B) QO © OQ () @) NARAYANAJEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 60. 61 62. Which of the following heterocyclic compound/s might be aromatic? {| he ®@ | be © {Ss o Grn Among the following , aromatic compounds are Co @ eo >= ows oO In which of the following reaction t-butylbenzene is formed? A) Benzene + iso-buty] chloride, AICI, B) Benzene + (CH,),C =CH, 5» C) Benzene + t-butyl alcohol —2% > teh D) Benzene + (CH,),C =CH, > Which of the following will show optical isomerism as well as geometrical isomerism cH, \ cu, A) CH,-CH=C=CH-CH, 8) a Nar, cH, cH, Ht, cH, a D) a ~~ N cig CH cu, cH, ° Which of the following compound will not show enolisation ' B) ° ‘or D) XC @) NARAYANA oat | IT-JEE ACADEMY-INDIA Page | 16 A)JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 64. Select the correet order among the following: A) Halide nucleophilicity in DMSO solvent is F- > Cl > Br > 1 . CL. -Q | Order of basie strength is H NH, WE NH dD) aA pu Order of basic strength, Le > > {only one enantiomers taken) ® 8 s Which of the following statements is incorrect about A and B? (A) A and B are mixture of diastereomers (B) Aand B are mixture of enantiomers (© Aand B are optically active (D) Bis optically active and A is optically inactive 66. The aleohol Oro on dehydration gave three isomeric alkenes A, B and C. one mole of each of these are subjected to ozonolysis. Then A gave one mole of dialdehyde B gave one mole of an aldehyde and one mole of ketone whereas C gave one mole of keto aldehyde, The correct statement(s) from the following is/are (A) In the formation of A from the reactant ring expansion takesplace. (B) In the formation of B from the reactant 1, 2-hydride shift takes place (©) Bis Hoffmann product (D) Cis Zaitsev product i): NARAYANA oat | IT-JEE ACADEMY-INDIA Page | 17JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 61. 68. 69. With reference to the scheme given below, which of the following statement(s about compounds (A) to (E)? ° Lil ALOs soch HBr/ROOR Ot © py HEIOOR 4g ey ne ty by, (A) Compound (B) releases a gas on treatment with sodium metal. (B) Compound (C) gives a resolvable mixture on reaction with Hg(Ac)2 followed by reduction with NaBH (C) Compound (D) does not exhibit geometrical isomerism. (D) ©) is a mixture containing achiral molecules. ‘The different kinds of isomerisms exhibited by the compound — CHsCOCH=CHCH(C)CHs is/are (A) Optical isomerism (B) Geometrical isomerism (©) Tautomerism (D) Conformational isomerism Which one of the following pairs of isomers are enentiomers AYANA CADEMY-INDIA Page | 18JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS CH CHS H—}—OH br H Br—j—-H_ H CH3 CHs D) 70. Which of the following pairs of compounds are diasteriomers? ou, om ot ou, fron toon won ww A poten nteon 8) toon ™ not oy, ou, cu, cu, th om zs = ies. Eh UbncY yA nbow won © ana D)__—Aitaan a a y P » H H H CH; oy, oH, NUMERICAL TYPE QUESTIONS 71. In the monochlorination of 3-methylpentane, let x be the number of pairs of isomers which exist as enantiomers, y be the number of pairs of isomers which exist as diastereomers, z be the number of isomers which are achiral. Calculate the value of (x y+2) 72. An alkene CsHi2(A) undergoes oxidative ozonolysis to give two different acids (B) and (C) Neither (B) nor (©) contains more than four carbon atoms. How many alkenes can satisfy this criteria? 73, The number of alkenes having higher heat of combustion than but-L-ene is, Ethene, propene, cis — but-2-ene, trans ~ but-2-ene, pent-l-ene, 2-methyprop-1-ene 74, ‘The number of sp* carbon atoms in the following molecule is ° 75, How many of the following groups are activating towards electrophilic aromatic substitution? ° NHCOR, — OCOR, ~ C-O-R, NR, ~ NH, ~ OH,-OR 76, Number of different products formed in mononitration of 1, 3 — dibromo benzene including minor produets is 77. How many of the following compounds are more reactive than benzene for EAS reaction ? i): NARAYANA oat | IT-JEE ACADEMY-INDIA Page | 19JEE abv ORGANIC CHEMISTRY PART-I(Jr)_JEE ADV IMPORTANT QUESTIONS OH =CH3 CHO COOH NH, CN OMe fe) te) ) w te) ) (a 6 78, Total number of stereoisomeric tetrabromides that will be formed in the following reaction is 28, AF aa, 79. How many saturated hydrocarbons can be prepared from alkenes of formula C,H,» excluding stereoisomers? (None of the structures contain quatemary carbon) PARAGRAPH TYPE QUESTIONS Q.NO: 80-81 Electrophilic substitutions are characteristic reaction of aromatic compounds, In this reaction hydrogen of the aromatic ring is replaced by an electophile because hydrogen in the form of H® is very good leaving group. COOH and —SOsH are also good leaving groups when they are present either at ortho or at para to the highly activating groups like —NH2 and —OH. 80, Which one of the following compounds will be most unreactive towards electrophilic substitution reaction? a NO, No: (A) B) ©) (D) “a Cs 5S a) 81. Benzene sulphonic acid is converted into benzene by (A) heating with dilute sulphuric acid (B) heating with dilute NaQH (© heating with soda lime (D) heating with Zine dust Paragraph for Questions 82 and 83 ‘Two compounds A and B of same molecular formula C4Hs gave the following reactions. a) Both discharged colour of Br: in CCl b) (A) gives a precipitate with ammonical AgNOs and on oxidation gives propanoie acid and CO» precipitate with ammonical AgNOs and on oxidation gives oxalic i) NARAYANA IT-JEE ACADEMY-INDIA Page | 20JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS acid and CO: 82, The compound (A) (A) HaC-CH2-CH=CH. (B) F2C=CH-CH=CH2 (©) HsC-C=C-CHs © ] 83, The compound () is (A) H2C=C=CH-CHs (B) H:C=CH-CH=CH: (©) HsC-C=C-CHs 1) yh for” estions 84 and 85 -H unit of an alkyne is more acidic than a C-H unit of an alkene or alkane, allowing acetylene and terminal alkynes to be converted to their conjugate bases =C 2 Unlike alkenes, alkynes are reduced by metals, especially Li, Na, and K 3 Unlike alkences, alkynes can undergo nucleophilic as well as electrophilic addition. -C=C- C %G uF Et EX isan ctecophite —™** is anucleophile 85. Which of the following best describes what happens in the first step in the mechanism of the reaction shown? CH3CHCHCHBr +3NaNH, “3 4c, {CHC =CNa+2NaBr+3NH; th > FLEN, = (CHCHCHy - CHBr HCH CHB ‘Br oa Br +: A) FEE) ° dD) G@).NARAYANA oat | IT-JEE ACADEMY-INDIA Page | 21JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS Paragraph for 86 and 87 “AT is 87. Product “C” is CO & .& 4 OO ,08 (oo , od Paragraph for Questions Nos. 88 to 90 ‘A hydrocarbon P (CuHs) on treatment with dilute HeSOs in presence of HgSOs forms Q(CuH20:). P on treatment with BsHo/H20: — NaOH gives R which is an isomer of Q. Q gives yellow precipitate with NaOT while R doesn’t, R forms a grey precipitate on treatment with ammoniacal silver nitrate solution. P on boiling with alkaline solution of KMnO, forms CsH04, which on heating with PsOio yields S(CsH,0s). S on treatment with toluene in presence of anhydrous AICIs yields T(CisH120s) as the major product. T is reduced by Zn- Hg/Con. HCl and produet obtained gives the following compound on reaction with HF SOO 88, Which of the following products are formed when Q is treated with aqueous NaOH? I mW IV (AT&IV (B) 1,1 & Cue ©) 1,1, W&IV ); NARAYANA oat | IT-JEE ACADEMY-INDIA Page | 22JEE abv ORGANIC CHEMISTRY PART- 89, Son heating with hydrazine hydrochloride gives A 9 (B) SN ‘NH i NH Oo Sh \ © 90, The structure of R is t cHo © Me ©) Me 0 ‘O 0 Me SHO ‘TWO COLUMN MATCHING 91. Consider the compound given below. Column-I has the reagents which react with this compound. Mateh the reactants in Column ~ I with the characteristics of the reactions in Column - II. chy re Column I Column II (A) | Dillute HaSO, (P) | Produces a mixture of two different carbonyl compounds (B) | OsO,/H202/H20 (Q) | Produces a mixture of two pairs of | enantiomers (© | Bromine water (R) | Involves cyclic intermediate. (D) | @ Os Gi) ZW/CHsCOOH | (S) | Product contains at least one alcohol ae i) NARAYANAJee abv 92. ORGANIC CHEMISTRY PART.I(Jr)_JEE ADV IMPORTANT QUESTIONS a Product on reaction with concentrated H;SO, produces a mixture of the reactant and its diastereomer. (A) A-ST-B-RS:C-RS;D-PR (©) APTB-QS« -PT:D-QT (B) A-RS:B-RT;C-PR:D-QR (D) A-QT:B-TS:C-QS:D-PQ ‘Match the multistep conversions in Column ~ I with appropriate sequence of reagents given in Column ~ IL. ‘Column T ‘Column IT @ NO, ®) | @Ac0 Co _. Gi) NOSBFy —- (iii) NaOH/A Hs ®) Q | @ Con HNOs/Con.H2S0, oO NO, Gi) AcO/anhyd. AIC oe Oo (R) | @ CHsCOCVanhyd AIC (ii) Con HNOw/Con H280, — NO, MY] Ae WA (8) | @ CHLCH2CH2CVanhyd. AIC O —- (ii) /BuCVanhyd.AICls —" (iii) Con HNOx/Con. H2SO; No, (D) | @ CHsCH2COCVanhd.AICs (ii) Con HNOw/Con.H2SO, (iii) NH2NH2/NaOH/elycol G@).NARAYANA I-JEE ACADEMY-INDIA Page | 24JEE abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS (A)A-S:B-R:C-T:D-Q (B) A-RB-S:C-T:D-P (OA-QB-RC-S:D-T () A-QB-P;C-S:D-T 93, Match List-1 with List-II and select the correct options given below List-I (Compound) List-II (Property) (P) Dihydro furan (2) Non-planar structure (Q Borazine (2) Antiaromatie R)Cyclooetatetraene (3) Aromatic (S) [12] Annulene (4) Five membered ring Codes: P Q R Ss (“2 3 1 4 ®) 4 1 2 3 © 4 3 1 2 QO 3 2 1 @) NARAYANAJee abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 94, 95, Match the column: [List - I List - 11 (P) Propanenitrile+MeMgBr —J77>—> a) oN @ Propanoylchloride+2MeMgBr —2 2 Q) AN (R) | Ethylethanoate+2MeMgBr —2"4_5 8) rr ° (S) | Propylmethanoate+2MeMgBr—i7>—> | (4) a Code P QRS P QRS @ 13 42 @n ne la, 7 ©3124 sae Ths Match the following ‘Column [(lon) ‘Column IT a, Hogs ACL () | Cation intermediate ty +e » —> HOW Db) x Haga a (q | Rearranged product ore el eatin 4 | os x AE © _ | Exhibits Isotopie(KyKp) effect hv ae O- d HS0, © __ | Rate of reaction increases in oo presence of EDG (A) APQRS, BPRS, CPQS, DPQRS (B) APRS, B9QR, CFQS, D>P.QS (©) AP.QS, B>P,S, C>P,S, D>P.R,S. (D) AP, 8, B2QS, CARS, D>P.QR NARAYANA I-JEE ACADEMY-INDIA Page | 26JEE abv ORGANIC CHEMISTRY PART-I(Jt) JEE ADV IMPORTANT QUESTIONS 96. Match the reactions in column I with appropriate properties of it in column IL Column I Column IT w CHO @)_ | Product exhibits stereoisomerism: NaBD, (81011 8) oe (Q)_| Does not involve carbocation intermediate cHey, Kon © oF (®)_| Eeletrophilic aromatic substitution Befexcon) SO3H Do oH CT S)_|Nacleophilic addition OO= (1)_ [Product is a di pair (A) A-PQT-B-RS.C-8:D-PQT (B) A-PSTB-RS,C-T.D-QST © A-QSTB-QS.C-RD-POS (D) A-PQST.B-QR:C-RD-PQR 97, Match the followin, COLUMN -1 ‘COLUMN — IT 0 ley P) | Geometrical isomerism 4g Yl u/\ gt ®) | Optical isomerism 9 1) | Tautomer or H2CH2OH = COzH 44. | @)NARAYANA oat IT-JEE ACADEMY-INDIA Page | 27Jee abv 98. ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS 4d) ” 4 ‘COacHec Heo “ = 4 H ce He02c XO 3D Meso (A)A-S;B=R: C-QD-P ()A-QB-P; C-R:D-8 (B)A-R:B-R; C=P:D-S ()A-S;B-QC-P,D-R Match the Following: Column —1 Column — Il TAG HDC ically active yf cuer (py | Optically activ pay Hf H ®) Ce (q | Optically inactive Me oO % (ey | Plane of symmetry HyCTROH Cols Dy | Ba, g (a) | Number of chiral centre = 1 cf cl (p | Number of of stereocentres = 2 (A) A-Q. B-QS: CRS, D-RT (©) AS; BRS; C PR; D-QT @) NARAYANA I-JEE ACADEMY-INDIA (B) AR; BPS; C-QR; D-QR (D) A-Q; BST; C-RT; D-RS Page | 28Jee abv 99. Match the followin, ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS a H (A) A-PQ; B-PQR; (C) APR: B-QRS 44. | @)NARAYANA I-JEE ACADEMY-INDIA ~ (B) A-QR: B-PQS: ‘Column = 1 Column =I A) CH (p) | 184-255. K¥imol I H F H 8 @ [142 Kiinol © @® [33 Kiimol ) CH; (8) | Zero! E CH, (D) APS, B-QRS Page | 29Jee abv 100. Match the Column Land IL ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS ‘Column -T ‘Column = TT a) D) Chiral centres containing compound H H \ tf c=C=C Br \ ‘Br b) @ Presence of stereocentre H. CH, CH, H °) 1) Optically active compound cL a 3) Compound containing plane of symmetry CH, C=N ae &% DAB, BPEE @APR.B-OQR CRS DPQ (©) A-QR: B-PR; C-QR: D-PR @) NARAYANA I-JEE ACADEMY-INDIA (D) A-PQ: B-QR: C-RS; D-PR Page | 30Jee abv ORGANIC CHEMISTRY PART- if) _JEE ADV IMPORTANT QUESTIONS KEY & SOLUTIONS: 1] D j2] a [3] c [4] p> |5] a 6 D 7 c 8 B 9 Cc 10 B 11 D 12 B 13 Cc 14 B 1s B 11) asa sf 08| sC|19| eee| 0) aC 21 D 22 c 23 A 24 Cc 25 D 26 A ae D 28 B 29 B 30 c EF [EE Ee 36 B 37 D 38 D 39 D 40 B 41 B 42 c 43 B 44 D 45 c 46||_a_47|__8 4s]_c_|49]_Bc_| 50] app 51||_ABC | 52| AB | 53 || ABCD B_ | 55|_ABD 56||_aB_|57|_BD_|ss||_BD BC_|60] ABD 61]|_aBc 62) cp os] aD ABCD | 65] BC 66 || aBcD |67| Ac 6s] aBcD ACD | 70| ABD zj__9 72) 4 [731 |74]_7 |zs]_4 7||_3 |77|_4 |7s]_s [79] 4 |so|_ . gi] _c ee] a |es|_s les] p les] .5 eB |e7|_c |es|_a_|e9]a so]. o]_a_|92/ 6 los] c joa] c os] c o6| D [o7[ 8 los] ps oof a ioo] c G@).NARAYANA I-JEE ACADEMY-INDIA Page |31JEE abv ORGANIC CHEMISTRY PART-I(Jr)_JEE ADV IMPORTANT QUESTIONS SOLUTIONS 5. 3°>2° > 1° follows stability of radicals, 6 ox Cl—CH,— C H—CH,—CH, cl-cn én cH, cn, 0 Cl-CH,— C H—CH,—CH, a) uh Cl-CH, —C—CH, —CH, 1 a @ cH, cl-cH, ~CH— cH, —cH, —cH, I FP 8 @ i C1-CH, -CH-CH. 7 ay Product _26%2 52 ProdutB 451 4 . %A~52.100=56.52% 92 8 ou c cates . Kuno, OH 0, CH. cH. NicuwyZ NanZ Now Z (Trans) 14. CH, -CH, —CH, ~C=CH, CH, - CH-C =CH cu, 19. Propyne contains acidic — H NARAYANA IT-JEE ACADEMY-INDIA Page | 32JEE abv ORGANIC CHEMISTRY PART-I(Jr)_JEE ADV IMPORTANT QUESTIONS 20. COs X= CK je B) (0) 21 OH Sem, 40H, pete, 85). Regarding “ CH3COOH ; B=CHxCOONa ;C =CH3 -CH3, D=CHy =CHy 23. Hydroboration followed by oxidation results in the addition a molecule of #7, In hydroboration oxidation Anti markovnikov product is formed. Syn addition 26. High hyper conjugation 27. Electron releasing groups on aromatic ring aetivates Electrophillic aromatic substitution reaction 28. © | — ji @— cc @+c0 | iS ¢ 31, Br &Fe 32, 3 moles of C,H, gives 1 mole of C,H,. 0.5 moles gives + moles of benzene. 0.5 moles of CH, obtained by the hydrolysis of | mole of 50% pure CaC, i) NARAYANA IT-JEE ACADEMY-INDIA Page | 33JEE abv ORGANIC CHEMISTRY PART-I(Jr)_JEE ADV IMPORTANT QUESTIONS 36 37, 38 39, 43, 44. 45. 47. 49. 50. During formation of C’* most stable in preferred as intermediate C** which attaches to Benzene. Poor 3 cet, ae — O-CH3 ci mple model, the transition-state leading to 1 involves diaxial opening of the epoxide ring. However, formation of dicquitorial isomer 2 requires a boat (or skew) like transition-state) re, diaxial opening of the epoxide ring to afford the diaxial product 1 is preferred Cis ‘cis addition meso compound Anti addition Higher the stability of the free radical formed lesser is the dissociation energy. Stability order of the radicals is H2C=CH - CHe> PhHsC-> MesC-> MexC In compound (B) and (C) chiral centres are present after hydrogenation and hydrogenation is syn addition 3° Alkyl halides gives elimination reaction with Lidl, Alkene which on reductive ozonolysis given only ethanal is 2-butene. So, other isomers of this alkene are H.C ~CH, CH= CH, 22249 51,0 CH, CH= 0+H-CH=0 and ots + CHy Hyo— /2ni4, 0. A =CHy 2H 5 Hgc-E=0 +H-CH=0 Hence, (A), (B) and (C) is correct answer @) NARAYANA I-JEE ACADEMY-INDIA Page | 34JEE abv ORGANIC CHEMISTRY PART-I(Jr)_JEE ADV IMPORTANT QUESTIONS 53. Methyl Ketones are formed from terminal alkynes. oO is obtained from either 54, : eS — ip Cosa, OO) Oe Og cael eS lea, we > Ce NO EOL ‘ = P eee 56. 4 5 2cH, ~ C-CHO+2CHO = 60. (14) Annulenes are aromatic B is more aromatic than A Fs on on ol ° — a — cH, cH, ‘on © bs, {e) CH cu, du, “1 Cl. Na/ary ether Br ca, ai o7 eu, 70. Diasteriomers are not mirror images of each other. Whereas enantiomers are non-supperimposable mirror images. a @) NARAYANA IT-JEE ACADEMY-INDIA Page | 35JEE abv ORGANIC CHEMISTRY PART-I(Jt) JEE ADV IMPORTANT QUESTIONS Hy CHCA CHC 3-methy! pentane monochlorination, different products, H are Hs otro Foros Chiral, one chiral carbon atom pair of enantiomers fi a Ge cH-g* Conc Chil earbon toms isomers. 2 pis of enantiomer 4 pairs of diastereomers. CHy-CHy-—CHs—CHy achial molecule 4 CH3—CH2—C—CH2—CH, —_achial molecule 1 X ~ number of pairs of enantiomers ~ Y = number of pairs of diastereomers = 4 Z= numbers of isomers which are achiral = 2 Total X+¥ +2 73. pent-I-ene 75. ~NR2. -NH2, OH and —OR are considered as strong activators. bbe 80. -NO2 group highly deactivate Benzene ring. 81. Benzene ring is highly deactivated due to -Cl group. 82. E 7 (je oo Oe p> OW Leow , $ i" i o SN ‘ OF Onn 86, 4 | @)NARAYANA ae IIT-JEE ACADEMY-INDIA Page | 36JEE abv ORGANIC CHEMISTRY PART-I(Jt) JEE ADV IMPORTANT QUESTIONS Red 68" spe . Br 88, 29, | @NA It AR RAYA NA Page | 37| @NA It AR RAYA NA Page | 38JEE abv ORGANIC CHEMISTRY PART-I(Jt) JEE ADV IMPORTANT QUESTIONS NARAYANA crass THE LION’S SHARE In JEE-ADV.2022 Buea 3402 RANKS OVERALL! ‘ALL ARE EXCLUSIVELY FROM 2 YRS. CLASSROOM TEACHING PROGRAMME bGGSOGSO SOOSHEICS > & S Page | 39JEE abv ORGANIC CHEMISTRY PART-I(Jr)_JEE ADV IMPORTANT QUESTIONS Oe NARAYANA’S INCREDIBLE RESULTS AN EVIDENCE For our consistent 43 years of academic excellence ol (All india Top Ranks Below 10 .0~ ) (All india Top Ranks Below 10 .0~ ) Ga L3S445 §88so10 (SF 151) 612) 44. oy eons Hee (WUD): TSEe ACADEMY-INDIA Page | 40