CHEMISTRY ALIPHATIC HYDROCARBON, OXIDATION-REDUCTION CONTENTS JEE EXERCISES EXERCISE-J-1...... EXERCISE-J-II EXERCISE-| EXERCISE-J-IV EXERCISE-J-V CHALLENGER EXERCISES EXERCISE-C-I HOME TESTS JEE MAINS. JEE ADV. ANSWER KEY” RATE OFELECTROPHILICADDITION Which of following is most reactive toward Bromination oxX eX ONWD oe The correct relative rate of reaction of the given alkenes for any given electrophiles is ° O. IDO cl 1 i i Iv (A)I>U>IV> M(B) > IV>m> 1 (Cy > > IV>1 (D)IV>1> > 1 Observe the following compounds CHy-CH=CH, CFy-CH=CH, (Sc CH, ot Vc CH, @ Q) @) @) The incorrect order of reactivity towards electrophile is (Ay 1>2 (B)3>1 (C)4>2 (D)4>3 ELECTROPHILIC ADDITION OF ALKENES Me-CH-CH-cH-ph “> w, Wis & (A) Me~ cH - cr (B) Me-CH-CH-CH,~Ph k ad (©) Me-CH-CH-CH, (D) cl-cH-cH-cH,-Ph ghd Le the {The product(s) of the following reaction can best be described as, HBr (A) Aracemic mixture (B)Asingle enantiomer (C)A pair of diastereomers (D)Anachiral molecule ‘The reaction of CH,CH = cw _\-on with HBr gives yy cx,crerct,<_Y—o1 (B) cn,cH,crer_\—o1 © cH,cHerc, Yer ©) cu.chcHe—_\—er10. u. 12. CH, -CH-CH=CH, — 82/04, X (major) | CH, Xwill be Pe er er eo i LI | ora -cr-bH-b4p (cy cry-b-cHip-dp py bHa-cH-dH-cH (A) O%-d-bs-cH (py 0-4 (cy Ste “E-Cha =e (py Oe 7 dhs des ba Hs CH. H ee iP . Cae Sa (x) products. Value of xis (Ay4 yl (C)2 (D)3 CH; H Yyac7 op H7~ “EL OS (A) Racemic mixture (B) Diastereomer (C) Mixture of Threo compounds (D) Meso compound Which of the following species is an intermediate in the reaction shown below : Br “OH ae) (B) OQ (Cc) O (D) fs 3 or of OL, ir Shape of intermediate produced during this reaction will be (A) Square planar (B) tetrahedral (C)Trigonal planar (D) Pyramidical (CH,-CH=CH, —2#2804_, (A). Product (A) is (A) >—on (B) CH,-CH,-CH,-OSO,OH © CHe-GHCH, (yA 0-S0,0HHs (ntgtoAe)a, HO 7 MH CH es CH; Hs @ To © emi 14, HY 0, OFF wXy, eX oX_ oA 15. yieame Hy", (X), (iH202,0H™ (1) Hg(OAC),, HO. (i) NaBH, (2) (X), (Y) and (Z) will be respectively (X, Y and Z are major products) waAg ay MAA Ot Kw AY Otte AKA, OY Aa A 16. Inwhichreaction(s) incorrect product(s) have been reported. (A) CH, = CH- CHO —HOK@NE10°C) Gis oH clo cl (B) CH, = CH COOH 29/4250. _, gtk CH, COOH OH 4, cH, I =CH-C—CH, —CTROH/H2SO. OH, CH— CH—G— CH, J ° OCH, 0 o-9 (C) CH= (Dy CH,-CH=CH-OcH, —CHOHIA oy. ch, cH —ocH, OCH,17. 18. 19, 20. 21. HCI/R.O,. x “LY 1B AN, Br Which is correct statement about X and Y. (A) Xs product of ionic reaction and Y is product of radical reaction. (B) X and Y both are product of ionic reaction. (©)X and both are product of radical reaction, (D) Xis product of radical reaction and Y is product of ionic reaction, ‘What is the product of the reaction shown below ? Ph-CH=CH-CH=CH-Ph 3, (A) Ph-CH,-CH=CH-—CH-Ph (B) Ph-CH,—CH -CH=CH-Ph Br Br © (O)-cH,-cHcit-cr,{O)-pr (D) Orai-cecrv-cn-C) ELECTROPHILIC ADDITION OF ALKYNES, Her C,H,C=CH — > °X’Xis- (tea) (A) C,H,CH=CHBr (B)C,H,CBr=CH, (© ericer= cer (D) C,H,HC = CBr, H _ Hg"/0® a Ph-C=C-CH,—CH, Za5;67 © Ais: (A) Ph-G~CH,-CH- CH, G8) Ph-§ POH, } b oD © oa i eemeieed (D) Ph--GD- CH, CH, CH, OH Identify final product inthe following ZcH cH HOBr/H*(2eq.) t f Bro gcH | C, ce CH wor cur, oy cH.8r oC or CuO)22. 23. 24, 26. 27. 28. 29. When propyne is treated with aqueous H,SO, in presence of HgSO,, the major producti: (A) propanal (B) propyl hydrogen sulphate (Cacetone (D) propanol fe} I HgSO,.dll. H.SQ. H-C=c-C-OoH——— 00 ° ° OHO ° Ii IL I 4 Il Il (A) CH,-C-C-OH (B) H-C-CH,-C-OH (C) CH,-CH-C-OH = (D) CH.-C-H The product(s) obtained via oxymercuation (HgSO, + H,SO,) of I-butyne would be— (A) CH, -CH, -C-CH, (B) CH,-CH,-CH,-CHO Il oO (C) CH,-CH,-CHO + HCHO (D) CH,-CH,-COOH + HCOOH HgSOq Hgso, CH,-C=CH ~y50, ? (A) ; CH, -C=C-CH, ot ®) Relation between (A) & (B), (A)Position isomers (B) Functional isomers (C) Homologous (D) Metamers B PTE CH CaCH —H880u/1S0. AA and Bare— H202,0H i i (A) CH3CHCHO,CH3 ~ C-CH3 (B) CH3 ~C -CHg CHyCH2CHO (C) CH,CH,CHO (both) (D) CH, E cH, (both) fe} ELECTROPHILICADDITION OF ALKADIENEAND ALKENYNE (CH,- C=C-CH, — CH = CH, @ ) Reactivity toward electrophilic addition reaction (A)a>b (B)b>a (ja=b (D) Cannot predict ‘The product obtained from the following sequence of reactions is He —c Sc 1980, NaBH. g ~ H,SO, (A) propanal (B) 2-propanol (©) 1-propanol (D) propane SOW Hc) + Product will be cl ZY ZN ~~ ORAZ ” a = a Pa30. 31. 32. 33. 34. 35. AF —Hens0re ‘Thermodynamically controlled product will be @) ae ®) Cc © C7 FREE RADICALADDITION AND SUBSTITUTION, Hy or pangs? Major product will be H, Hy, Br eS) Ce ®) OF © Co ‘Br +H ES?) (major product) Structure of (x) will be (A) So (B) on © Ch Anti-Markownikoff’s addition of HBris not observed in - (A) Propene (B) But-2-ene (C) Butene CH, O —NES_, Major product will be CH, Sr Br wo ®) Oo oO), Br (D) ane Br CH, o SI Br cl IG “O (D) 1-Methyl cyclohexene (all OXIDATION OF ALKENES AND ALKYNES Beayer's reagent is (A)alkaline permanganate solution (B) acidified permanganate solution (© neutral permanganate solution (D) aqueous bromine solution36, 37. 38, 39, 40. 41. 42, 44, Which of the following will decolourise alkaline KMnO, solution? (A) CH, (B) CH, (cel, (D) CH, Inthe given reaction: a CataikMoo OH OH _giOH (A) : (B) © CO : (D) Band C both MOH OH MOH Os Znstho Product are (A) >=0 =o (B) 0 /=9 (C/O P=, (D) 0 DO Baeyer’s reagent decolourises which ofthe following, (A)Alkane (B)Alkene only (C)Alkene and alkyne both (D) None of the above 1-Butyne WP", x + -¥ Identify XandY? (A) CH,CH,CH,COOH + 0, (B) CH,CH,COOH (©) CH,CH,COOH + CO, + H,0 (D) CH,CH,COCH, + HCOOH Q Reagent R, CO Reagent R, Q :R, and R, are Hof “OH HOt H (A) Cold alkaline KMnO,, OsO,/H,O, (B) Cold alkaline KMnO,, HCO,H & H,O* (C)Cold alkaline KMn0,,C,H,CO,H (D) C,H,CO,H, HCO,H Ozonolysis of CH, CH-C-CH, will give (A) Only CH,CHO (B) Only HCHO (Only co, (D) Mixture of CH,CHO, HCHO & CO, OTHER OXIDISING AGENT Glucose as well as fructose are oxidized by periodic acid. The number of moles of HCOOH formed from each mole of glucose and fructose are (A) Sands (B)Sand4 (©)Sand3 (D) 4and3 Which of the following compounds is resistant to per iodic acid oxidation ? (A) GHOH (B) GH.OH (©) CH.OH () { OH 0 gt qHoH HOH CH,OH CH,OH CH,OH45. 46. 47. 48. 49. 50. 53. Secondary alechols on heating with copper at 300°C give (A)Alkenes (B)Aldehydes (©) Ketones (D)tert-aleohols REDUCINGAGENT HY (A) ey ott © e7 (D)B&C both HD DOD Product of above reaction is (A)racemic (B) Diastereomers (©) Enantiomer (D) None Which of the following reagent not gives syn addition when react with alkene. (A) H, + Pd (CaCO, + Quinoline) (ByPt (C)Raney Nickel (D) Li/lig. NH, : a He cold Kn ‘ CH, CHy Spica, (A) SSL (B). Compound (B)is (A) Meso (B)Racemicmixture (C)Diastereomers _(D)All CH,-C=C-CH, —™, (a) —22Kitnou_, (By 3 3 gis (A) Meso (B)Racemic mixture (C)Diastereomers _(D)All 5 ay CH,-C=C—CH, He (A) “cay” B) (A) Meso (B)Racemicmixture (C)Diastereomers _(D)All Lindo p Cac RSM, 9 Catalyst A and B are geometrical isomers (R-CH=CH-R)— (A)Ais trans, Bis cis (B) Aand B both are cis (C)Aand B both are trans (D)Aiscis, Bis trans Which of the following reagents converts both acetaldehyde and acetone to alkanes? (A)Ni/HH, (B)LiAIH, (©) L/NaOH (D)Zn-Hg/cone.HCL54, 55. 58. 60. Stephen reduction (SnCl,/ HCI) converts cyanides to (A)Aldehydes (B) Ketones (C)Amines (D)Acids When benzoic acidis treated with LiAlH, it forms (A)Benzaldehyde _(B)Benzylaleohol_—_ (C) Benzene (D) Toluene B Molt (cH =cH-cHo Hea AandBare respectively: (A) ()-oncn.cH0 , Con =CH~CH,OH (B) ()-oncr.cro1 . (cn =CH—CH,OH © ()-cn=cn CHO in both case (D) ()rencticron in both case R-CO-O-R' disobu| _, y 4 ROH ‘aluminium hydride ‘The product Y is (A)R-CH,-OH (B) R-CHO, (C) R-COOH (D)R-CH, REACTIONS OFALKANE O —<2-> (A), Product (A) will be: cl (A) O (B) O © CO () CO Methyl cyclohexane react with Br, in presence of u.v light major product will be oC) ~ 6) CL © Ce ©) Cr ‘Br Br Ct —S1 (x) monochloro product (aye (Bs 9 (p)1061. 62. 63. 65. 66. 67. [en Shs (x) Product Xis — (xismonochloroproduct) (Aya (B)6 9 (D)10 —22 + (X) Di-chloro product (A) (B)6 @7 (D)8 Major product for the reaction (> esis PREPARATION OF ALKANE , ALKENE AND ALKYNE ~Cl+CH,-CH,-Cl ae? products. Which of the following is not the free radical combination product in wurtz process. (A) CH, ~CH, (B) CH, ~ CH, ~CH, (C) CH, ~ CH, ~ CH, ~CH, (D)CH, Ate Major product (A) is aL) <] 8) © a ©) cre CH, Hy CH. CH, CH, (a) cH, ®) wy © Cr © , wo ©) CO © O 0) ©68. 69. 70. 1. n. BB. Which of the gases evolved on the surface of anode, (A) Hy, He (B) CH, H, (C) C,H, + C,H, + CO, (D) CjHg + CyHjy + CO, ] ONa” _Electoyss_, major product will be ONa’ (A) I-butyne (B) n-butane (©)2-butene (D)2-butyne Gases liberated atthe surface of anode and cathode respectively in kolbe's electrolytic syntheis will be (A)H,, CO, (B) CO), Hy (©) NaOH, H, (D)Onlyco, Sodium Benzoate —ya5q-eaq Product will be ; A Cy) ®) OL J ©) OO Rate of decarboxylation of following carboxylic acid with sodalime will be in order cH, COOH MSO NaoHsca0. CH, CH, COOH ~~? cH, Naol-C20. CH,-CH-COOH (A) > Pty (B) Pry >r (Qn>m>n (D) >> Which of the following undergoes decarboxylation most readily on being heated ? ° OL, Loon (B) Chan i) HO“S00 9 ° © wo LOL Bog, oO tn. Oo HO“So,74, 75. 76. But-2-ene can be obtained by electrolysis of an aqueous solution of: (A)2,3-Dimethyl maleic acid (B)2,2-Dimethyl butanedioic acid (©)2-Methylbutanedioie acid (D)2,3-Dimethylbutanedioie acid cH,cH,cl + cH,CH,Li Ss x > nNonane (A) The compound ‘X” is (CH,CH,),CuLi. —_ (B) The compound ‘X” is CH,(CH,),CH,Br. (C) The compound” is (CH,CH,),CuLi, _ (D) The compound “Y” is CH,(CH,),CH,Br. Acetylene may be prepared by electrolysis of (A) potassium oxalate (B) potassium acetate (C)potassium maleate (D) potassium succinate Ts—_§- RATE OF ELECTROPHILIC ADDITION ‘What will be order of reactivity of following compounds towards addition of HBr? CHA CH Ph CH, -CH=CH-CH, C=CH, I | CHS Ph-C=CH-CH, Ph-C=CH-CH, . 1 1 Iv ‘The acid catalysed hydration follows following order (CH,),C=CH, > CH,CH Explain this order of reactivity. ELECTROPHILIC ADDITION OF ALKENES, Give product of the following reactions. mA () pr SO 2 oll tea, @ 4 Hom, What will happen when BrCl, react with (a) cis But-2-ene (b) trans But-2-ene. FREE RADICALADDITION AND SUBSTITUTION Predict the product of the reaction below 1H, > CH,=CH, CH,-CH,-CH-CH, 52> or ost CH, =CH-CH,~CH, "8, B+C write structure of Band C. OXIDATION OF ALKENES ANDALKYNES Write the structural formulas for the products formed when 3-heptyne reacts with KMnO, under ? (neutral condition at room temp. (i) alkaline or acidic condition athigher temp. Complete the following reactions ‘CH=CH, Qe @ KMnO, ry 80, Cold di. KM. ne) RCOHIH®10. u. 12. 13, 14, OTHER OXIDISINGAGENT Complete the following reactions oH CH,-CH-CH-CH, tH. be k Ho to, Pert fs io, @ CK > © dy OH On OH e) CH-C-CH-CH, MO. , ©) ini * Complete the following reactions cus s00°c ro OH >——————>P HiKnO/s so —PCC or Colin's reagent pECE or Fotis eager SR Ho” OH MnO - Complete the following reactions : cH, cua (@) Ph-CH-CH.-OH —S"-> ; (b) Pr-cht-cH, AS (0) Pinto ow, on cH, REDUCINGAGENT C=C (y) Natta _ —te_, (X), What are (X) and (Y) in above reaction? Undters cnalyst Write the hydrogenation product of following species (a) CH,=CH-CH,-CH,-C=C-CH, =), (oy cH-cH cH, cH, C-c cH, HHSC, (©) Benzoylchloride —*2P¥ 8521, Give reaction conditions (reagents and/or catalyst) for effecting the following conversions CHHCH), (CH,),CH, —> Se-cd He te (CH)-CH, (i) CH(CH)), H bay CH.-CH, (ii) > 115, 16. 17. 18. 19. ‘What is the product of each reaction UAH, folloned by HO EE ened LOAN (i) PhCHO NaBH, followed by H.O B LAID folowed by WHO 9 bow, LIAL followed by 0,0 [LAH followed ty 0,0 (i) } | Nebo folowed by EOH, D, ‘oom temperature D REACTIONS OFALKANE How do you account for formation of ethane during chlorination of methane ? Give the major product of monobromination of following compounds. (a) oO (b) O or @ O PREPARATION OF ALKANE ,ALKENE AND ALKYNE Write the major product of following reactions of ne -tree Br (i) VW, Naldry ether Natty ether, r (iii) Ph-Br+CH,-Br _Naldry ether _, (report mixture) Hooc— POOH mor, [xy Bitlis coon COOH Te—$§$§___ @sp—____— ONE OR MORE THAN ONE CORRECT TYPE QUESTIONS 1 Ofte following, unsaturated hydrocarbons are— (Aethyne (B) cyclohexane (C)n-propane (D)ethene CHs b Cl, / ho Ph-CH,-CH-CH3 “(monochiorination) > Which statements is/are correct about photochemical chlorination of the above compound ? (A) The major product will have chiral carbon atom but is optically inactive. (B) The intermediate free radical of the major product is resonance stabilised. (C) The intermediate free radical is tertiary for major product. (D) The intermediate free radical is planar, and stabilised only by hyperconjugation Which of the following catalysts is/are used for partial reduction of alkyne ? (A) Na/NH,() (B) Ni,B or P-2catalyst (©) Lindlarcatalyst (D) Rossenmund catalyst eo X) ow) eS A (X) will be OONa (A) A coona (B) Cone (Cc) 4 (D) coon Which of he following is not produced as an Intermediate during the reaction O Br Na es Cer (A) Ope. (B) ©: © OK ) OF? In which of the reactions, a gem-dichloride product is formed. Dry ether (A) CHC = CH E> (B) Ph =< (©) CH,=CH-cl 4, (D) CH,=CH-CH, _seiccu In which of following reaction racemic mixture will form. oe CHN UH tier (A) CH, - CH, — CH= CH. > (B) C=C. > s—CH, beck wero, CH, ‘CH, +) CHS b _ ter, © De xq car (D) None (cis) 1710, =CHCH,CH=CH, —“®S + possible products can be. a Ch = CHEHCH= CH, (B) CH,=CHCH=CH-CH,Br Br (C) CH, = CH CH, CH = CHBr (D) Ch = cHeHze = Ce Br Which of the following will give same product with HBr in presence or absence of peroxide. (A)Cyclohexene _(B) I-methyleyclohexene (C) 1, 2-dimethylcyclohexene (D) 1-butene Analkene on ozonolysis yields only ethanal. There are an structural isomers of this which on ozonolysis yields: (A) propanone (B)ethanal (C)methanal (D) only propanal PARAGRAPH #1 A hydrocarbon X with molecular formula C,H, on hydroboration-oxidation give an aldehydey Y and on oxymecuration-demecuration give ketone-Z. Compound Y and Z are functional isomers, Compound X on treat- ment with HOC! give compound P and on treatment with HCI give compound Q. Ha(OAc). Bh. wor A ne Tear Tenet) Il, Thestructure of Xis: (A) CH,-C=C-CH, (B)CH-CH,C=CH_ (C)CH,=CH-CH=CH, —— (D) CH,=CH-C=CH 12. ‘The correct statement is (A) Pand Q are positional isomers. (B) Qis 1,2-Dichlorobutane, (©)Pis 1,1-Dichlorobutan-2-one. (D)PandQ are identical. PARAGRAPH #2 The alkenes which form more stable carbocation intermediate are more reactive towards addition of 11,0 in presence of dil. H,SO, 13, The correct order of reactivity of following alkenes is, (1) Ethene (2)Propenoicacid —_(3) Butenedioic acid (A)3>2>1 (B)2>1>3 (C)1>2>3 (D)1>3>2 14, Thecorrectorder of alkene reactivity is mentioned in- (A) CE 1,=CI 1-Cl> Ck 1,=Ck 1-OCH, (B) CE 1,=CHCI1 propene (D) CH, = CH- OCH, > CHy 18PARAGRAPH #3 15, 16, 17. 18, ‘The halogens, Br, and Cl,, add to alkanes. When the electrons of the alkene approach a molecule of Br; or Cl, one of the halogen atoms accepts them and releases the shared electrons to the other halogen atom. Therefore, in an electrophilic addtion reaction, Br, behaves as if it were Br* and Br, and Cl, behaves as if it were Cl’ and cr. —»:BrCH,CH.Br: 4,2-dibromoethane ‘a bromonium ion a vicinal dibromide cis-2-butene 852, coy How many products will obtained in this reaction (A)1 (B)2 (3 (D)4 1 CH,-CH=CH, > (A) Os cH, ba oH. Br Reagent (X) and (Y) in above reaction. (A) X=1,, Y=NaBr (B) X= Br,, Y=Nal (C)X=NaBr,Y=1, (D)X=1,Y=Br, Observe the following compound and match the reagents of List - land List I &) ° Reagents - I Functional group oxidised / reduced — II (A) CrO,/ Pyridine /CH,Cl, ® w (B) NaBH, @ =z (©) Na/C,H,OH ® x @) Cr0,/H* oy Column-t Column-I Reactant and reagents Products A) pp 000Me iter, (PR) phon + MeOH py A200 HME) gy RHO MOH © py 000ME _ ns Oe + MeOH DO) pe OOOME_ teva, ye 000Me () — Noreaction 1519, 20, 21. 22. 23, 24, INTEGERTYPE Gen He, CH; ‘Total number of Markownikoft's products in above reaction is? ed cel, Me ‘Number of products obtained in the above reaction is? oy 8 ‘Total number of products obtained in this reaction is? ‘The number of possible enantiomer pairs that can be produced during monochlorination of 2-Methylbutane is Me, Et =< wer Ev ‘Me How many product will be formed in above reaction. Gli OH a C0 HO——H Ona H——}—0H (i) H— +n _ sito. (ij) HOH _ sito, — ae H—1—ou CHLOH CH,OH Sum of moles of formaldehyde obtained in the reaction (i) and reaction (i) ? 20ED an But-I-ene may be converted to butane by reaction with = [AIEEE-2003] (A)Zn—HCI (B)Sn—HCI (C)Zn—Hg (D) Pd/H, Which one of the following is reduced with Zn, Hg and HCI acid to give the corresponding hydrocarbon? [ATEEE-2004] (A)Ethylacetate —(B)Butan-2-one_——_(C) Acetamide (D)Acetic acid The best reagent to convert pent-3-en-2-ol into pent-3-ene-2-one is [AIEEE-2005] (A) Pyridinium chloro-chromate (B) Chromic anhydride in glacial acetic acid (C)Acidie dichromate (D) Acidic permanganate Acid catalyzed hydration of alkenes except ethene leads to the formation of | [AIEEE-2005] (A) Mixture of secondary and tertiary alcohols (B) Mixture of primary and secondary alcohols (C) Secondary or tertiary alcohol (D)Primary alcohol 2-Methylbutane on reacting with bromine in the presence of sunlight gives mainly? [AIEEE-2005] (A) 1-Bromo-3-methylbutane (B) 1-Bromo-2-methylbutane (C)2-Bromo-3-methylbutane (D)2-Dromo-2-methylbutane Which of the following reactions will yield 2,2-dibromopropane ? [AIEEE-2007] (A) CH,-C=CH + 2HBr —> (B) CH,CH=CHBr + HBr —> (C) CH=CH + 2HBr —+ (D) CH,-CH=CH, + HBr —> Inthe following sequence of reactions, alkene forms the compound ‘B” [AIEEE-2008} CH,CH-CHCH,—*> A" > B, The compound B is (A)CH,COCH, — (B)CH,CH,COCH, (C)CH,CHO (D) CH,CH,CHO One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a molecular mass of 44 u. Thealkene is [AIEEE-2010] (A) propane (B) L-butene (C)2-butene (D)ethene 2-Hexyne gives trans -2-Hexene on treatment with IAIEEE-2012] (A)PUH, (B)Li/NH, (©) Pa/BasO, (D)LiAIH, 2i. 12, 14, Inthe given transformation, which the following is the most appropriate reagent ? [AIEEE-2012] CH=CHCOCH, CH=CHCH,CH, Ho- H (A)NH.NH, OH (B)Zn-HgHCI(C)Na, Liq, NH, (D) NaBH, How many chiral compounds are possible on monochlorination of 2-methylbutane? [AIEEE-2012} (A)8 (B)2 ©4 (6 Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of mono substi- tuted alkyl halide? [AIEEE-2012} (A) Tertiary butyl chloride (B) Neopentane (C)Isohexane (D) Neohexane The most suitable reagent for the conversion of R-CH,-OH ~> R-CHO is [JEE Mains-2014] (A)KMn0, (B) K,Cr,0, (C) C10, (D) PCC (Pyridinium Chlorochromate) In the hydroboration-oxidation reaction of propene with diborane, HO, and NaOH, the organic compound formed is: [JEE -Main 2014] (A) CH,CH,OH (B) CH,CHOHCH, (C) CH,CH,CH,OH (D) (CH,),COH (oy rc “HC CH-CHyCH>OH wor rgres oO -CHy CH; OH CHSCH-CH CH;-COOH oO Tee oy Hy on mercuration-dimercuration produces the major product [JEE -Main 2014] 217. 18. Inthe following sequence of reactions Toluene #0. A —S0°h_, BEEF 5 C the product Cis [JEE Mains-2015] (A)C,H,COOH ~~ (B)C,H.CH, (C)C.HsCH,OH —(D)C,H;CHO 3-Methyl-pent-2-ene on reaction with HBr in presence of peroxide forms an additon product. The number of possible stereoisomers for the product is : [JEE -Main 2017] (A) Four (B) Six (C) Zero (D) Two The trans alkenes are formed by the reducation of alkynes with [JEE -Main 2018] (A) NaliqNH, (B)Sn-HCI (©) H,-PdiC,BaSO, (D) NaBH, 2Ep 1, What would be the major product in the following reaction ? [IIT 2000} a Hy ‘CH, ~Tindlar catalyst” 2. Which one of the following alkenes will react fastest with H, under catalytic hydrogenation condition— (IT +2000) R R R R H R R R YY VJ ———< =x 8 >< Oo SX OX H nt R H R H R R 3. Propyne and propene can be distinguished by— [IIT *2000) (A)cone.H,SO, — (B) Br, inCCl, (C)dil. KMnO, (D)AgNO, in ammonia 4, Statement-1 _1-butene on reaction with HBr in the presence of a peroxide produces 1-bromobutane. Statement-2 _Itinvolves the formation ofa primary radical. [IT 2000] (A) Statement-1 is true, Statement-2 is true and Statement-2 is correct explanation for Statement-1 (B) Statement-1 is tue, Statement-2.is true and Statement-2 is NOT the correct explanation for Statement-1 (©) Statement-1 is true, Statement-2 is false (D) Statement-1 is false, Statement-2 is true 5. _ Inthe presence of peroxide, hydrogen chloride and hydrogen iodide do not give anti-Markovnikov addition to alkene because — [HLT +2001) (A) both are highly ionic (B) oneiis oxidising and the other is reducing (C)one of the step is endothermic in both the cases (D) Allthe steps are exothermic in both cases. Me 4 a cH, C=C a H H Hydrogenation of the above compound in the presence of poisoned paladium catalyst gives — (A) An optically active compound (B)An optically inactive compound +2001] (C)Aracemic mixture (D)A diastereomeric mixture10. 12, 13. The reaction of propene with HOC! proceeds via the addition of — {IIT *2001) (A) H’ in first step (B)CI’ in frst step (© OFF in frst step (D) Ct" and OFF in single step Statement-1 Dimethyl sulphideis commonly used for the reduction of an ozonide ofan alkene to get the carbonyl ‘compound, [IT 2001] Statement-2 _Itreduces the ozonide giving water soluble dimethyl sulphoxide and excess of it evaporates. (A) Statement-1 is true, Statement-2 is true and Statement-2 is correct explanation for Statement-1 (B) Statement-1 is true, Statement-2.is true and Statement-2 is NOT the correct explanation for Statement-1 (C) Statement-1 is true, Statement-2 is false (D) Statement-1 is false, Statement-2 is true Statement-1 Addition of bromine to trans-2-butene yields meso-2, 3-dibromo butane, Statement-2 Bromine addition to an alkenes an electrophilic addition. (UIT 2001] (A) Statement-1 is true, Statement-2 is true and Statement-2 is correct explanation for Statement-1 (B) Statement-1 is true, Statement-2 is true and Statement-2 is NOT the correct explanation for Statement-1 (C) Statement-1 is tue, Statement-2 is false (D) Statement-1 is false, Statement-2s true Consider the following reactions — [IT 2002] HyC-CH-CH-CH, + Br >‘X’ + HBr DCH; Tdentify the structure of the major product *X” (A) HyC-GH- GH-CHy (B) HxG-GH-G- Cy D CH; DB CHs © HsC-@-GH-CHy (D) HyC-CH-GH-CH D CH CH, Identify a reagent from the following list which can easily distinguish between 1—butyne and 2-butyne- (A) bromine, CCI, (B) H,, Lindlar catalyst [ur +2002) (C)dilute H,SO,, HgSO, (D)ammonical CuCl, solution CyH-C=C-CH, B81, A [IT ‘2003] 1,50, m wNXo) o ¥XO) (C) CeHs-C=CHCH; (D) CeHs CH= C—CHy on ou OH 1 x By AR Tito” (mixture) 225 compounds of molecular formula C,HsBr, Number of compounds in X will be: {IT +2003) (ay2 (B)3 (4 (D)s a14, 16, 17. 18, 19, 20. 21. 2-hexyne can be converted into trans~2-hexene by the action of : [UT +2004) (A)H,-Pd-BaSO, (B)Liinliqg.NH, — (C) Hy PLO, (D) NaBH, 2-phenyl propene on acidic hydration, gives [1T 2004) (A) 2-phenyl-2-propanol (B) 2-phenyl-1-propanol (C) 3-phenyl-1-propanol (D) 1-pheny!-2-propanol How many chiral compounds are possible on mono chlorination of 2-methyl butane? [UIT 2004) (A)2 (B) 4 (C6 (p)8 1-bromo-3-chlorocyclobutane when treated with two equivalents of Na, in the presence of ether which of the following will be formed? (HIT +2005) Br cl (A) (R) («c) (D) CH,-CH=CH, + NOCI ->P [HIT 2006] Identify the adduct. (A) CH; -CH-CH, (B) Cy - GH- GH 4 No No cl ye «© cise ciaa cl (D) CHa CHa ~ Gla ec NO cl CH; HE Ch.bw_, N(isomeric products) C,H, Cl —setionat disaion_, MI(isomeric products) Hy What are N and M? (A) 6,6 (B) 6,4 (C)4,4 (D)3,3 [IIT 2006} The number of stereoisomers obtained by bromination of trans-2-butene is [117 2007] (A) (B)2 (C3 (D)4 Intermediate produced when propene react with HCI in presence of peroxide e @ (A) CHg ~ CH, ~ CH, (B) CH, ~CH-CHy (©) CHy -CH,CH, (D) CHs -GH-CH3 Te22, 26. ‘The maximum number of isomers (including stereoisomers) that are possible on monochlorination of the following, compound, is [JEE-2011] CH, ©. ch.cH/ | NcH,cH, H Consider all possible isomeric ketones, including stereoisomers of MW = 100. All these isomers are idependently reacted with NaBH, (NOTE : stereoisomers are also reacted separately). The total number of ketones that give a racemic product(s) is/are [JEE Advance-2014] Inthe following reaction, the major product is, [JEE Advance 2015] ls CH, _1 equivalent Hr H.C OH, (CHy Hs A) B) A A Hy Bre Br Br CH, CH, © oe (D) ac The correct statement(s) for the following addition reactions is(are) : [JEE-Advanced 2017] H Br/CHCI, Manin Gi HG _CH. _ Br/CHCl, ae <= = o uy, an w@ an (A) (Mand 0) and (N and P) are two pairs of enantiomers (B) Bromination proceeds through trans-addition in both the reactions (C) (Mand 0) and (N and P) are two pairs of diastereomers (D) Oand P are identical molecules Total number of hydroxyl groups present in a molecule of the major product P is [JEE-Advanced 2019] — i)Hy,PS Ba Tdi KMa0,(e quinoline Syiak> P 27p Br Y ‘i ii i “ae oe Se a wy © Br Br HBr H Br 8D (THE , CH “yor on” P, incorrect about product p A) Ithas two B)Pi CH cag! (A) Ithas two stereoisomer (B)Produetis | Se=C< (C) Cyclic Transition State Formed (D) stereospecific syn addition 2 so oD BO of of cl > ‘o_ Divether cr wl (B) oD (D) nd cl O Ng BEN WN PR () Ng BEN MN BR ONS Correct order of rate of reaction will be (AVIV>WI> I> (By I> IV >1> i (C)IV>1> I> (D) Noneof these Inkolbe's electrolytic synthesis the pOH of solution will be (A) decreases (B) Increases (© Constant (D) None of these aCH, Ho nt “ar * oa at H oH dy, ote @ a) te) Correct order of mono bromination of given compound is ()I>M>I ®I>I>M Ol>i>m jm M>1>1 8. Pick the correct statement for monochlorination of R-secbutyl chloride. Me oy i 5 cr a 300°C Bt (A) There are four posible products; three are optically active ones optically inactive (B) Thereare five possible products ; three are optically inactive & two are optically active (C) Thereare five possible products; two are optically inactive & three are optically active (D) There re four possible products ; two are optically active & two are optically inactive 9, Statement-1 Addition of Br, to I-butene gives two optical isomers. Statement-2 The product contains one asymmetric carbon, (A) Statement-I is true, Statement-2 is trueand Statement-2 is correct explanation for Statement-1 (B) Staement-1is tre, Statement-2strucand Satement-2is NOT the correct explanation for Statement-1 (C) Statement-| is true, Statement-2 is false (D) Statement-1is false, Statement-2s true HBr Br CHa, 10. STATEMENT-1: on ow Ne CH car Minor ea Br \ on AnH SH = 20°C Major Minor - + cH, STATEMENT-2:¢,7-\ 2% Hs gp SN gp cS CH Allylic cation Be afl CH, Br cH SN 3 CH, on Ae * major at of high temp major at low temp :i. 12, 13. 14. (A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1 (B) Statement- is True, Statement-2 is True; Statement-2 is NOT a correct explanation for Statement-1 (C) Statement-1 is True, Statement-2 is False (D)Statement-1 is False, Statement-2 is True (A)2 (B)3 (4 (Ds The reaction of HBr with the following compound would produce Br - O- Br a Br © ¢\ {> om’ \ Me CH, CH, _ HBr coy, What is stereochemistry of products (A) Optically inactive (B)Meso product (C)Diastereomers___ (D) None of these Consider the following rearrangement. Select the structure of the intermediate that has correct mechanistic arrows accounting properly for the transformation. He 0. y HQ Hy w( Sk of XX oC Yk ) Hy 3016, 17. 18, 19, 20. Me (A) Diastereoisomers (B)Enantiomers (C) Positional isomers (D) Single meso compound o aa Ni Me Product of above reaction is (A) Meso (B)racemic (©)Diastereomers _ (D) Optically inactive mixture Oo O 4s Ni Me Product of above reaction is (A) Meso (B)Racemie (©) Diastereomers _(D) Optically active products. =0-cH,-cH=ch-cH,-E-c1 (a) (b) (c) Reactivity toward catalytic hydrogenation (A)a>b>e (B)b>a>c (Ca>c>b (D)c>a>b Which of the following is produced as an intermediate when 2-Butyne react with lithium in presence of liquid ammonia. wl (B) \_/ © \—/ ©) -_ A compound (C,H,) reacts with ammonical AgNO, to givea white precipitate and reacts with excess of KMnO, solution to give (CH,),;CH-COOH. Ihe compound is — (A) CH,=CH-CH=CH-CH, (B) (CH,),CH-C=CH (©) CH,(CH,),C=CH (D) (CH,),C=C=CH, 3121. 2. 2. 24, 25. ‘What is the major organic product of the following reaction ? (\== “io.” W804 (A) (B) o* H © (D) fe} Which of following is least reactive toward hydrogenation ? (A) CH;- C=C - CH, (B) CH C=CH (©) HC=CH (D) HC = CH, OH x rz. x Hy D, “CH, papaso, (A) yr? ®) Product (B) of above reaction is CH CH, CH, H——D H—+—D “A (B) H—_+— D—7—H cH, CH, H CH; H—7—D. D—y—H © (D) H——D H—7—D H Et Product (B) is (A)Racemicmixture (B)Diastereomer __(C) Pairof Enantiomer (D) None The products of the following [and II sequence are related as (HyPacaco, i) By/CCL, y_ —OPaCeCo, BHCC, 9 CH, -C =C-CHy 7 BCU HIPS. (A)Diastereomers _(B) Identical (C)Enantiomers (D) geometrical isomers 3226. 27. 28. 29, 30. 31. [- i EEN Major product will be (A)Z-3-Hexene —_(B) E-3 Hexene (C)E-2-Hexene (D)A&B both Analkyne C,H,, on reaction with alk. KMnO, and subsequent acidification with HC1 yields a mixture of CHg - CHCOOH + CH,CH,COOH. The alkyne is— bi (A)3-Hexyne (B)2-Methyl-3-hexyne (C)2-Methyl-2-hexyne (D)2-Methyl-2-hexene ONE OR MORE THAN CORRECT TYPE Which of the given compounds can be the main products of following reaction CH, ~ CH= CH, _Bfp/aq NaCl+Nal+NaNOs (A) CH, - oH = oH. (B) CH, ~ oH ~CHONO; — (C) cH,-CH-CH, (D) CH.~ GH os oH rot Br Cl Br 1 Br OH Br In-which of following reaction diastereomer will form. CH, CH, o rie sm, Ae 2 ca oj CH, by, (A) Only! (B) Hand Ill (C) land I (D)I, Hand It Nm GS (i)NaHCOs 1H: Stereochemistry of product will be (A) Optically active (B) Optically inactive (C)Recemic mixture (D) Meso Bromination can take place at \ oD Npsihv (l (B)2 (3 (D)4 3332. 33. 34. Br CH-CHs CH-CHs NBS Which of the following statements are correct for above reaction. (A) Reaction intermediate is carbocation. (B) Product is mixture of two enantiomers. (C) Reaction intermediate is stabilized by +1, hyperconjugation & resonance. (D)Br,at high temperature also give same product in the place of NBS. A ots Inthe given reaction, ¢,H,, U2» cl ) (major) Structure of X can be cH, CH, C>-cu=ch, O © O oo) Identify the incorrect statement(s): (A) Alkynes are more reactive than alkenes towards electrophilic addition reaction (B) Alkynes are less reactive than alkenes towards electrophilic addition reaction (C)Alkynes decolourise Br, water (D) Addition of HBr to alkynes in presence of peroxide proceeds via Markownikoff’s addition, 34ne EE Comprehension # 1 Me \ ag tit BA 8880, 5) thine gp) MOL Na+ lig. NHs kali >eGH >) “Fo, >) 1. The compound (C) is Et Et Et H (A) » < (B) =~ (C) Et-=-Et (D) Both (A) and (B) aH 4 a 2. The compound (F)is: Et, Et Et, JH (A) » < (B) -=* (C) Et—=-Et (D) Both (A) and (B) HOH 4 a 3. Thecompound (D) is Et Et Et H -OH He OH HO—4—H Ae Toy Bye ty © pL oy Both) and (©) et et Et 4. The compound (G) is Et Et et H: OH H ‘OH HO——H A, on ® ho H (©) y—t on —(D) Both (B) and (C) et et et 5. The compound (E) is (A) Two moles of Me Ncuo. (B) Two moles of Me coon, (C) One mole of (A) and one mole of (B) —__(D) No reaction. Comprehension #2 ‘Three acyclic alkenes (x, y,2) on catalytic hydrogenation give same alkane, On reaction with HCl, (x, yz) form same major tertiary halide product. Reductive ozonolysis of mixture of (x, y,) gives a mixture oftwo moles of CH,=0 one moles of CH,CH=O one mole of acetone, one mole of butanone and one mole of 2-methyl propanal. x, yand z do not have any stereoisomers. 6 x,yzare (A)chainisomers _ (B) Position isomers (C) Geometrical isomers (D) Optical isomers(x,y,z) 2 » addition product. The correct statement is (A)All three alkenes will give 3 different major hydration products (B) Three alkenes will give same hydration major product (C) Twoalkenes form same product but one alkene forms different major product. (D) Addition of HCI and H,O* both are following different regioselectivity. What is true about x, y, z. (A) These have molecular formula C,H, (B)x,y,z on catalytic hydrogenation give chiral alkanes. (C) These are unbranched alkenes. (D) These form same carbocation intermediate on reaction with HCI to give the major product. Column-I ‘Column-II «a (P)— Racemicmixture ® (Q Reduction ofalkene or alkyne © (R) Meso (D) — Oct-2, 6-diyne —Lindats_, (S) _ Diastereomer Catalyst 3610. 12. 13. Match the reactants in column I writh product in column II: Column Column It (A) CaC, + H,0 (p) CH, -C=C-CH, (B)Mg,C; + H,0 (q) CH,-C=CH i HOM Kolbe a osc H-6-E-0K ° (D) H-¢-d-ox —Kote_, | Clectrlyie Ko-G-C-H Oo (E) CHI, ae (t) CH, —CH, er te Ll an (yon, -e-gn OT (u) CH - CHI, Br Br C.H.OH Br Br (G) on -b-f-on oo (wv) CHF = GH Br Br Br Br (w) CH, - C= G- CH, be be For the given reaction how many products are optically active (all isomers) CHy CH | \ Bx thw CH ~C—CH, ~CH-CHy | CH; Number of structural isomers which can be obtained on monochlorination of 2-Methylbutane is : When trans-2-butene reacts with Br,/CCl,, X number of products are formed. Whereas when trans-2-butene reacts with HBr Y number of produets are formed. Report your answer as YX. 3714, Number of reactions which give alcoholas product. cn (a) HIP. ° O° i ocr Hp/PdIBaSO, °O a or Te oO (a) NaBH, /THE NO, (e) Na/NHa(¢) ‘CaHs0H 3ep ” 6. 1 ind the reagents a, b, c & d for the following reactions : a. ky a, \el HOD ~. b, (hy a OH DoH c, Ou Lo, OHH Sodium salt of which acid will be needed for preparation of propane ? Write chemical equation for the reaction. A metallic carbide on treatment with water gives a colourless gas which burns readily in air and gives a precipitate with ammonical silver nitrate solution. The gas evolved is Inthe reaction sequence, A HBL (CH).0, ©O-cx =cH-cH, 8 B What is the relationship between A& B: Write the hydrogenation product of following species with H/Pd. (@) 1,2-Butadiene —"*> (b) trans-2-butene 24> (c) Benzaldehyde "> Complete the following reactions (i) CH,-CH,-C=C-CH,~(CH, ),-CH,OH ae inHg cooH i) (7S) Naina, OL nee Identify a and b, in the following reactions NaBH, 9 NaBH. o [-CHOH > * al NHO | Po @ | (i) a4 LAH, 7 ee 0 Oo" “cH, When t-Butanol and n-Butanol are separately treated with a few drops of dilute KMn0, in one case only, the purple colour disappears and a brown precipitate is formed. Which of the two alcohols gives the above reaction and which is the brown precipitate.Time :- 60 min. Total Marks: 120 Instructions 1 All question are of equal marks 2. Marking [+4,-1) 1. Whichalkene onheating with alkaline KMnO, solution gives acetoneanda gas, which tums lime water milky. (A)2-Methyl-2-butene (B) Isobutylene (©)1-Butene (D)2-Butene He 2 aaa Product of above reaction is (A)Racemic (B)Diastereomers_(C)Enantiomer (D) Meso 3. C,H,, (P) has two types of alkenes that can be reduced to one type of C,H, , (Q). Qis: WAAAY @)< on (Ondine 4. m-Pentane 22> (A) Mono-chloro product (including streoisomers) are (ay2 (B)3 4 (5 5. Which of the following alkanes can be synthesized by the Wurtz reaction in good yield ? (A) (CH)),CH-CH, ~CH(CH,), (B) (CH,),CH -CH, ~CH,~CH (CH,), (C) CH, — CH, ~ C(CH,),CH, ~ CH, (D) (CH 7 7 6. Which ofthe following will form cyclohexane on reaction with two moles of Nain ether (A) CH, CH, - Br wo )-* (© Br-CH,-CH,-CH,-CH-CH,-CH,-CI_ (C) ot) Br 7. Which acid will decarboxylate with greatest difficulty ? IL O Oo 0 CH,-C-CH,-COOH (A) (B) © (D) § a10. u. 12. 13. 14, Propyne and propene can be distinguished by (A)Cone.H,$0, (B) Br, inCCl, (C)Dil.KMnO, ——_(D) AgNO, inammonia ‘The product of following reaction is , On PhCH=CHCH=0 Fj 4,6 (A) PhCH,CH=CHCH,OH (B) Ph(OH)C=CHCH, (©) PhCH=CHCH,OH (D) PhCH,CH,CH,-OH cocl CHO a x C) Xeanbe (A) NaBH/EtOH = (B)LiAIH/THF = (C) Na/EtOH (D) HPd-BaSO, Which of the following reagent not convert carbonyl compound into alcohol ? (A)DiBAL—H (B) NH—NHJKOH (C)Na—Hg/HCl_ (0) LiAIH, NF BNF xis (A) Br, /H,O (B) HBr (C)HBr/Peroxide (D)NBS Which of the following reactions is not an electrophilic addition reactions — we TT ae Br Hs, of T as Oe TT rae Inthe free radical chlorination of Methane, the chain initiating step involves the formation of (A) Chlorine radical (B) Hydrogen chloride (C) Methyl radical (D) Chloromethyl radical. Which of the following is the major product for the given reaction ? Wess (A)2-Bromo-2-methylpentane (B) I-Bromo-2-methylpentane (C)4-Bromo-2-methylpentane (D) 3-Bromo-2-methylpentane Ph-CH=CH-CH, H9C!, x, xis: OH cl (a) Ph-CH-GH-CH, ) Ph-CH.GH-CH, ca OH (C)Ph-CH=CH-CH.CL () o-{O)- over on aT17, 18, 19. 20. 21. 22. OL + HBr —2%_, Product : Product is Br Br Br @ ) © Cx ©) Ce Inthe reaction of chlorine with propene at 450°C, the major product is cl cl cl Ma Ba Loa OA () oN ‘The reagent system for preparing propan - 1-ol from propene is (A) Hg(Ac)/H,0 followedbyNaBH, —_(B) H,SO,/H,0 (©)BH, followed by HO, (D) HCO,H/E,S\ ‘The major product ofthe following reaction is CH,-CH = CH, + HBr (C400). (A) CH,-CH,-CH,-Br (B) CH.-CH(Bn)-CH, (© BrCl-Cll= Cl, ([>—e ‘The major product formed upon addition of | mole of HBr in the following reactions is Oo —hetimele) Major product ? Br @) ® Co~ © ©) er ‘Br ‘Br ‘Br ‘The major product in the following reaction is L.BHs, THE23. 24, 25. 26. 27. 28. Identify the alkene which will not provide the following aleohol upon oxymercuration demercuration. rs q l (CS (B) (C) (D) i ‘The major product of the following reaction is (CH),C-CH-CH,-CH, —082He-ther i 02, NaOH OH H (A) SL (B) —~ © ae (D) ye ‘The product obtained from the following sequenee of reactions is cn H9SO, 9 NABH. H.C —C =CH “HsO, ” —+ (A) propanal (B)2-propanol (C) L-propanol (D) propane 2 ySeexene Prost ‘The correct name of the product obtained is (A)cis-1,2-dibromocyclohexane (B) cis-1,4-dibromocyclohexane (C)trans-1,2-dibromocyclohexane (D) trans-1,4-dibromocyclohexane ‘The correct order of reactivity of alkene towards an electrophile is mentioned in (A) CH,=CH-Cl> CH,=CH-OCH, (B) CH,=CHCI < CH,=CCL, (C) CH=CH, > CH,-CH=CH, (D) CH,= CH - OCH, > CH,=CH-CH,-OH The reaction of one equivalent of HBr with CH,-CH-CH,-C=CH gives: (A) CH,=CH-CH,-C=CBr (B) CH,=CH-CH,-c = CH be =CH-CH,-CH=CHBr (©) CH-cH-CH, be CH wc a29. 30, Match List I (reaction) with List Il (type of reaction) and select the correct answer using the code given below the List- I lists List-1 (P)— Ph-CH.-cH, =" a (Q Ph-CH=CH, —4#52._, Q) (R) Ph-CH=CH, S82, @) (S) Ph-CH,-cH, 22> @ Codes P Q sR Ss PQ @m 1 ot 2 4 ®) 3 2 © 4 2 3 1 @) 1 2 CH, HTD Bry /ho Het—H 2!" , product, major product will be CH, CH, CH, H D H: D (A) H¢- Br (B) pr. CH, (C) BothA and B CH, CH, Home test JEE (Main) Objective Response Sheet Electrophilic substitution Electrophilic addition Free radical substitution Free radical addition R s 4 3 4 aTime :- 60 min, Total Marks:- 87 SINGLE CORRECT TYPE [+3,-1] ‘Compound (A) on oxidation with hot KMnO, / OH® gives two compound ° CHy -CH-COOH & CH, -G-CH:CH,CHs , compound A will have structure oH (A) CHCH, ~ = C-CH;CHy (B) CH ~CH-CH=C~CH,CH,CH. das Oy by ty (C) CHyCH-C-=C-CHy (D) CHs ~GH-C = C-CH-CHy bey by by CH,-C=C-CH, —“*— (A) 22> (B) Tights eCle (A) Meso (B)Racemic mixture (C)Diastereomers — (D) All Ph-CH=CH, © ,P, Identify major product 'P'is (A) Ph-GH-CH.-cl_ (B) Ph-GH-CH-1 (C) Ph-gH-CH-cl(D) Ph-GH-CH.-1 1 a a I CH cHtp-d-cH=cHy, 81284, x Hy, CHy CH (i(A20), Ha. THEO, y chy-du-d ch i) NaBH, CH, CH, Io ) cH, -6 = b-cH, —O8#e™R, 7 (ii) Hz /OH (A) All three products (X,Y, Z) are different, (B)X and Y are identical but Z is different. (C)Y and Z are identical but X is different, _ (D) All three products (X, Y, Z) are identical. Which of the following is the best reagent to convert 1-Methylcyclohexene into 2-methylcyclohexanol ? (A) Dil H,SO, (B) Hg (OAc), / NaBH, , H,O (©)B,HJH,O,, OH (D) Conc. H,SO, cECH, ~ CH, ~ OH po OF on pana o ee X, Y, Z reaction are: (A) Simple hydration reaction (B) Hydroboration oxidation, hydration and oxymercuration demercuration (©) Hydroboration oxidation, oxymercuration demercuration and hydration, (D) Oxymercuration demercuration, hydroboration oxidation and hydration. ONE OR MORE THAN ONE CORRECT TYPE [+5, 0} In which of the following reaction reactants and products are correctly matched ? (A) F,C-CH=CH, + HCL — F.0-fH-H, a 9° I (B) CH,-CH = CH-C-OCH, + IC —> CH,-CH-H-C-OCH, ail (© C,H,CH = CHCH, + HBr 29° 5 4H, aie cH, nor oc. Roo The correct statement(s) is/are Ph H Nome ner nat of No (A) Itisa regioselective addition reaction, which forms (B) The reaction intermediate is paramagnetic. (C)ltisa free radical chain reaction. (D) The product has two chiral carbon atoms ti Markownikov's addition product. a69. 10. i. CH, esr onmo4i8e ‘True statement about above reaction : (A) Reagent involve stereospecific syn addition of Hand OH species. (B) Product obtained is trans isomer. (©) Boron atom acts as electrophile. (D) two stereoisomers are obtained as product ‘Trans-2-Butene —H°®", p (product) Ps: CH, cH, CH, CH. Hon. Hon Her Ht Mi e® ee © pln ore CH, CH, CH, CH. (~~cHo eo Xis ~cn (~ ~cooMe (A) (B) sj cOOMe © (D) a7PARAGRAPH TYPE QUESTION [+4, 0] Comprehension # 1 ° ° (Pe Mutt © Pate (a) {in EtOD ° | Nab, EtOH ®) 12. (P)and(Q) respectively are 9° OH ° De oD OH 1H @) . oD 1H OH ‘OH oO OD DO o ©) , é0 13. Riis op eae 9D O © He ©) OD 1D a14, 16. 17. 18. MATCH THE COLUMN TYPE QUESTION [+8, 0] Match the reactants given in Column-I with the reagent given in Column-I for the preparation of cyclobutane Column-t Column-IL cook re) (p) A, NH, ~NH, /KOH coon COOH (B) (q) Na/ ether é 00H © () NaOH/Ca0/A, Zn-Hg/HCl ‘COOH (D) Cl-CH,-(CH,), ~CH,- Cl (8) Electrolysis, H/Ni INTEGER TYPE QUESTION [+4, 0] CH, -CH-CH,- CH, -CH, a oH, Mono-chloro product (includingstreoisomers) are How many alkenes react faster than propene with dil.H,SO,? Pt Ph CH, (b) d) . aA wy © oy @ HR _ HN Vy ote, oO 7a HuPéBaS0, | _ DJ BIN x. numoer of products y ) LLNaINH (iG), DUN, ¥ number of products Find the value of x+y How many reactions are correct? 1H 1H ay CI Cre my BOA COOH No, No, Z of) sestbt OO (iii) ramoynors_, NCH NN CH: Che AY CH HH H——D ww sano, 7D ©) yre=eQ, 2 HT CHy a15, 22, 29, 36. 43. 50, 57, 64, n. 16, 23 30. 37. 44. 51 58. 65 72. PUumMmBNUAAaw o> Prrwwowwore IV>M>I>1 10. 17. 24, 31 38. 4s. 52, 59, 66, B. VUN>Aw>r>yrdy 18, 25. 32, 39, 46. 53. 60, 67. 74, EXERCISE J-I AS. ic 12, A 19, Cc 2. A 33, Cc 40. D417. Ds 54. B61 Cc 688. D745. EXERCISE J-I1 Reactivity is based on stability of intermediate carbocation. 3° carbocation > 2° carbocation > ° carbocation (stability order) ® A CHe-CHs- CHs-CHp Br Br () mone 1 (a)Racemic mixture of 2,3-Dibromobutane _ (b) Meso2,3-Di 13 20, 27, 34, 41 48, 55. 62, 69, 76, vuowruonowwera avawuwrwangs HO. (d) ibromobutane 14, 21 28 35 42. 49. 56 63. 70, wUwW>oOrwras CH, =CH-CH-CH, + CH, ~CH=CH-CH, I I Br Br (CH,CH tor (ii) CH,CH,COOH + HOOCCH,CH,CH, 00 CH,-CH, COOH Ot COOH KMno, (a) aes (b) BANOS oH Cold dl, KMnO, cae ne coon H 0O4 (1) Peracia aa HO" "WOH10. 13. 15. ‘CH=O0, @ H=0 (b)2 HCHO + 2 HCOOH (c) CH,COOH + CH,CHO 0 0 Gap 0 OE «GE CHO O Hooc CHO O } (a) Ph-cH.-cH-oH —SM4 > ph_cl-cH=o (©) Ph-cH-cH, ula, ph_o-cH, OH cH, © re oh CHA 5 prs oC, cH, cu, CO 9D Cis trans (a) CH,=CH-CH,-CH,- =C-CH, SES), CH,-CH,-CH-CH,-CH,-CH;-CH, CH.=CH-CH-CHN CH, (b) CH,=CH-CH,-CH,-C=C-CH, HPSE280.,, oN (cis isomer) (©) Benzaldehyde (Benzene carbaldehyde) (i) H/Pd-BaSO, Gi) Inthis conversion -CO- converts into~CH,— which can be achieved by any one of the following reagents (a) NH,-NH,/KOH/A (b) Zn-Hg, Cone HCI, A bocy, bic, been, boc, ()A=PhCHOH B= PhCH,OH (A= B= D= Chlorination of methane is a free radical reaction which occurs by the following mechanism Initiation ao Xgl —temerision, 2cf Propagation cH,-H+é1 —+ GH, +HCI GH, +1-c1 —> CH,-Cl+ cf Termination GH, + 6H, —> CH,~CH, GH, +1 —» CH,-Cl +g — cl-cl19. 15. 17. 19, 14, 21 15, 22. 29, 10. i Br ® QO @ (b) or 0 onpr EXERCISE J-IIL AD 2. AB 3 ABCD 4, cD SS. AB 9. AC 10. AC IL B 12, B 16. = B (A)- (a) ; (B) = (8) :(C) (ps); (D) — (4, 8) 18. 2 20. #2 21 2 22. 2 23, EXERCISE J-IV D 4, Ca, Cc. 9. B 10, uC 12, A 16. D 700A 18. A EXERCISE J-V cH cH, Noe Teese A 3 D 4 B 8. A 9. B 10. B i A A B ib. A 16. B 7 D418. B 22. 8 23. 5 24. D 25, EXERCISE C-1 B 2, Bo 3 Bo 4 c c 8. A 10 A IL B 16. C 17. C 18, D 23. A 24. AC 25. D 30. BD 31. ACD 32 A 2 B 3 A 4, D5, D 9. A-P,Q;B,-QR;C-Q;D-Q (A)- (8); (B)- 45 (C)-s; (D)-s3(E)-s; (F)-45(g)-P 4 1204 13. 210 14.3 : (d) (iii) Ph-Ph + CH,-CH, + Ph-CH, cD 6. ABC 7. ci B.C 14, ABC D (A) = (Pp) 5 (B) — (4) (C) = (®) ; (D) ~ (s). 4 24.03 D6 A 7. B B.D 14. D 12. A 13. A 19 B20. BC 26. 6 A 7. Cc 14. B21 B28. AD aa 0 cDEXERCISE C-IIl (a) (1) BH, / CH,COOD CH,CH,CH, ~ COONa + NaOH —S22> CH,CH,CH, + Na,CO, CH, GHCOONa + NaOH —E> CH, - CH, ~ CH, + Na,CO, CH, CH, Positional isomers (a)Butane — (b) Butane (c) Ph-CH,-OH COOH (@)CH,-CH,-CH = CH-(CH,),-CH,-OH oO} COOH () CH,-CH,- CH= CH(CH,),-CH,-OH oO ° oH ,H oH ho. NH ZO i NH, (ia: , b Ho Ho” Hi, cH, t-Butanol is not oxidised by dilute KMnO,, so it does not give brown-black precipitate of MnO, n-Butanol is oxidised with dil KMnO, and MnO, is converted to brown-black precipitate of MnO,. Me Me ‘OH DKW, , No reaction Me t-Butanol Me- Am nBuanol Ct t+ CH,CH,CH,COOH + MnO, 4 (Brown black ppt.) + 2KOH + 2,014. 17. 16, w> pow 30, Bo 2. ABCD 9. 23. Dee Ds 10. B 17. D 24, Cc A 3 ABCD 10. HOME TEST JEE MAIN Bo 4. cS, B D ol. B 2 D Cc 18. C 19. C D 2%. B 2 C HOME TEST JEEADV. Bo4, D5, cc AD Il AB 12) D 15. 8 16. (A)- (1); (B)-() 5 ©)- (8); D)-@) 3 18. 13 20, 27, 6. 13 wu paa Cc iG 28, 6(a,b,c.d,e,g) Ow>> BCD Er