KX &ercise vm Marked ques ns are recommended for Re jon. PART -1: SUBJECTIVE QUESTIONS Section (A) : Reduction-1 AA. AQ Az Ad, Write the hydrogenation product of following species with Ha/Pd. (a) 1,2-Butadiene —2/"s_, (b) trans-2-butene —t/Ps_, H, ath (c) Benzaldehyde —!!?4_, () KOS HgtPi CH, 169 (Limonene) Write the hydrogenation product of following species (@) CHe=CH-CH2-CHs-C=C-CHs Hess), (b) CHo=CH-CH2-CHz-C=C-CH, —teiPeBaS0_, (c) Benzoylchloride —te/P#/8s804_, Complete the following reactions : (i) CHs-CH2-C=C-CH>~(CHa)s-CH20H am COOH w (Nain, w HO Give reaction conditions (reagents and/or catalyst) for effecting the following conversions CHACH. (CH.)-CH, (i) CHs{CHe)-C=C-{CH2)-CHs —> Dose H H CCH, CH,-CH, &6 Section (B) : Reduction-2 Ba. What is the product of each reaction 9 LIA. followed by H.0 LAID. folowed by HO LIAIH, followed by H.0 Boca eee ccereeaane Sane) AIH, followed by D,0 (iy) PhCHO> Ww | NaBH, flowed by H.O [NaB0 followed by EtOH [Ses tees ee jeer Tea, , Tom temperatureB-2.%3. Identify a and b, in the following reactions : NaBH, °. eUNEBH Hats : o CHOH” (i) ad Y LAH, 4, 9 NaBH, No | a (i) Oo 4 LAI, sb 07*cH, B-3. Complete the following reactions : 9 (a) AI(OCHMe;), (b) fears — (CH;-CH-CH, oH CHO Section (C) : Oxidation-1 C-4.a Write the structural formulas for the products formed when 3-heptyne reacts with KMnO« under ? ) neutral condition at room temp. alkaline or acidic condition at higher temp. C-2. Complete the following reactions : CH, CH,-CH, KMn\ KMnO, (a) Seat (b) Seite KMnO, co . 0G RCOHH C-3. When t-Butanol and n-Butanol are separately treated with a few drops of dilute KMnOs 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. [IT-JEE, 1994] Section (D) : Oxidation-2 D-1.x» Complete the following reactions : ,OH Ms Ho, oo Pegg gts io. ore pete. a = G — OH OHOH OH * OOH * "OH D-2. Complete the following reactions : Cu/ 300°C Ho. JOH re eereeercmrcraeereee HiKMnO/s Gg [PC or Cots agent Ho” OH MnO _D-3= Complete the following reactions : CH, L Cula (@) Ph-cH,-cH,-on —“4 5 ; (6) Ph-GH.CH, cA, Pr-c-on —Gl OH cH, Section (E) : Hydrolysis E-1. Write the products of following reaction O_O. HO" =“ E-2. Write the products of following reaction (a) CHs-C=N 4°, (b) CHsNc sO _, E-3, Reactant 8°”, CHsCOOH + HCI E-4. CHsCONH: 2°", Products : E-5. The hydrolysis of acid anhydride produces NHCOCH, E6. QO te, Product is No, E-7. Reactant (CsHe0) 8°, CHsCHO + CHsOH PART - Il: ONLY ONE OPTION CORRECT TYPE Section (A) : Reduction-1 A-1. The relative rates of hydrogenation is in the order of (A) CHa = CH2> RCH = CHe > RCH = CHR > RzC = CHR (B) RoC = CHR > RCH = CHR > RCH = CHa > CH = CH (C) RCH = CHR > RoC = CHR > RCH = CHe > CH, (D) RoC = CHR > CH2 = CHa > RCH = CHR > RCH ‘A-2. _ In which case the reaction is most exothermic with He / Ni. Ie Geese ce A-3. An organic compound with molecular formula CeHio is not reduced by Hz / Pd / BaSOs. From the given options, the compounds may be : O ~~ GQ ~ " u v ALI (8), (cy (oy ii, HA (CH, fi HPL A-4. u aA x, xis CH.” CH, (A) Only (R,R) product (B) Only (S,S) product (C) Meso compound (D) Racemic mixtureASS. AS. AT. AB. One Na/NHs(") , p, the product can be : CiHOH ol (©) (0) eae roduct Cre |. (C) Both (A) and (B) (0) None of these Which of the following reagents converts both acetaldehyde and acetone to alkanes ? (A) Ni/He (B) LiAIHs (C) hNaOH (D) Zn-Hg/conc.HCI ‘Stephen reduction (SnCle/ HCl) converts cyanides to (A) Aldehydes (B) Ketones (C) Amines (0) Acids Section (B) : Reduction-2 Bt B.2. B-3. Baw When benzoic acid is treated with LiAlHs, it forms (A) Benzaldehyde (8) Benzyl alcohol (C) Benzene (D) Toluene Name the reaction 9 OH I A\(OCHMe.), I Me-= -C-Me ——ay-Gq? Me- = -CH-Me CH.-CH-CH, OH (A) Meervein-Ponndorf-verley reduction (8) Wolff-kishner reduction (C) Bouveault-Blanc reduction (0) Stephen's reduction R-C=N —SBAHHO , Product ~40%e The product formed is : (A) R-CO-NH2 (B) R-CHe-NHe (C)R-CHO (D) R-CHz-NO2 p< NaBH C)-ctectt-cro HPC, g Aand B are respectively : (A) Oyen CH,CHO, ()-ctte-ctie-ctteon (6) oi es CH,CH,OH , ()-cre-ctt-cttron ‘CH-CH,-CH,-OH in both case (0) oe in both caseB-5. _ Inthe following reaction CoHsOCzHs + 4H "®4P*"!_, 2x + H20, X is (A) Ethane (B) Ethylene (C) Butane (0) Propane B46. R-CO-O-R’ sisobuiyl__, y +R’ OH ‘aluminium hydride “78°C The product Y is (A) R-CH2-OH (8) R-CHO (©) R-COOH (0) R-CHs B-7.—_ What are A and B in the following ? 0 9 «Raney Nit oor els OH wy in all cases OCTCS nace 1H (C) in all cases OH OH oY ee eel Section (C) : Oxidation-1 C-1.. Baeyer's reagent decolourises which of the following : (A) Alkane (B) Alkene only (C) Alkene and alkyne both (D) Benzene ( ( €-2, Ethanol on reaction with alkaline KMnOs gives: (A) Ethanal (B) Giyoxal (C) Acetic acid (0) Acrolein. C3. 1-Butyne MMOs, x+y Identity X and ¥ 2 (A) CHsCH2CH2COOH + O2 (8) CHsCH.COOH (C) CHsCH:COOH + COz+ HO (D) CHsCH-COCHs + HCOOH C4. An alkyne CrHi2 when reacted with alkaline KMnOs followed by acidification by HCI, yielded a mixture of CHy -CH-COOH & CHsCH:COOH. The alkyne is - I CHy (A) 3-hexyne. (B) 2-methyl-2-hexyne (C) 2-methyl-3-hexyne (D) 3-methyl-2-hexyne Reagent R, Reagent R, c-5. ———— —! ; Ri and Ro are HO! “OH HO! IH (A) Cold alkaline KMnOs, OsO«/H202 (B) Cold alkaline KMnOs, HCO:H & H30* (C) Cold alkaline KMnOs, CsHsCO3H (D) CsHsCO3H, HCOsHSection (D) : Oxidation-2 Dans D2 D-3. D4 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) Sand 5 (8) Sand 4 (C) Sand 3 (0) 4 and 3 ‘Secondary alcohols on heating with copper at 300°C give (A) Alkenes (8) Aldehydes (C) Ketones (0) tert-alcohols, The reagent, with which both acetaldehyde and acetone react easily is (A) Tollens reagent (8) Schiffs reagent (C) Hz/ Ni (0) Fehiing’s solution Which of the following compounds is resistant to periodic acid oxidation ? GH.OH GH.OH GH.OH ‘O H, HOH gen wf @ of © buon CH,OH HOH CH,OH ce Section (E) : Hydrolysis E4. £3. What product is obtained when Benzenecarbonitrle is hydrolysed. (A) Benzoylchloride (8) Benzenecarboxamide (C) Benzaldehyde (D) Benzoic acid The acid catalysed hydrolysis products in the following reaction are - ee eee pa CHO CHO COOH | CH-OH CHO CH,-OH COOH CHO Al &l 8) & I Ol & Ln & I CHO CHO HH CH,-OH CHO CH,-OH (OOH ~=CHO oe Ho" ——_— Product obtained in above reaction are : OH 9 9 9 (A) EtOH, CO (8) CO CHs-CHO = (C) CHs3COOH, O (D) EtOH, O PART - Ill : MATCH THE COLUMN Observe the following compound and match the reagents of List-| and List-II (x) 9 (y) Ho ‘CHO 2) HONe. won, ° Reagents-1 Functional group oxidised / reduced (A)_| CrOs / Pyridine / CH2Cle ) |W (8) _| NaBHy @) |Z (C)_| Na/CxHsOH () [x (0) GrO37H* @)_1Y2. _Match the following column: Column-t T Column-ll Reactant and reagents Products: ‘COOM A) | pp eo ari rte ©) | Phot + Meo A OOOMe {))DIBAL-H (-78°C) ‘CHO (8) | PhS ee | | pS Meo ‘SOOM ‘CHO (C) | pps sa | Me SF MeOH COOMe | © | Mes HesParc | me @_[ No reaction v Marked questions are recommended for Revision. PART ONLY ONE OPTION CORRECT TYPE CHO | H—C—OH 1. Ate Hon Heating with HI py HC—OH buon ‘Aand B can be : (A) Both are n-Hexane (B) Both are Hexan-1,2,3,4,5,6-hexaol (C) Ais n-Hexane B is Hexan-1,2,3,4,5,6-hexaol (0) Ais Hexan-1,2,3,4,5,6-hexaol and B is n-Hexane H ~ 1 Ho -C=C—CH,-CH, Zz =C-CH,-CH, 4 Y) ~ HC-¢=G-CH.-CH, HH In the above reaction the using reagents X and Y are ; (A) Nal liq. NHa for X (B) He, Pd/ BaSOs for Y (C) BHs-THF + CHsCOOH for Y (D) All of these are correct. 3am 0 aaa (a) —H, (By —Fetting solution, (€) Red colour ; (B) is : wre bs (8) CHs-CHO (C) CH-COOH (D) HCOOH48, Te Consider reduction of 2-butanone. NaBb. NaBD. sa NaBD, He 8 C=C. aa ) ce o Bh yO H—+~>p CHy GH-OH C=0 CHO HO—}—H us i @ sH0, iy 17 —0H H—}— oH H——}—0H H———H H—— 0H CH,OH CH,OH ‘Sum of moles of formaldehyde obtained in the reaction (i) and reaction (i) ? How many of following reactions are hydrolysis reactions ? (1) CHs-COOH + C2Hs0H (2) CHrf-OC:H, _no"_, ° @) Siri io. (4) CHs-Cen 42, ae OO atin Z 6) ZA iace ‘ae, (6) CHs-CH=NH —"2_, CHO Hy (7) CHz=CH-O-CzHs 18° _, (8) CL te, 0” “ocH, How many of the following may produce salicylic acid on hydrolysis under appropriate conditions ? CN \ Oy NH OH o H ( NC iH 1 (iv) (v)PART - Ill : ONE OR MORE THAN ONE OPTIONS CORRECT TYPE 4. Which of the following catalysts is/are used for partial reduction of alkyne ? (A) Na/NHs(/) (B) NizB or P-2catalyst (C) Lindlar catalyst (D) Rossenmund catalyst ~~ ~cHO 2X Beal Xin : 2.20 COOMe cN ~~cn (~~ ~cooMe é f (A) (B) (c) (D) 3. Identify the possible structure of X and Y KMnO, / OH/A om resolution CH,O —>~————>_ d+F (Kory) K,Cr,0,/H,SO, LEEROIMSO:, Blue green salt + other products Xx ¥ Ph-CH—CH, CH, Ph-CH,—CH-CH, (A) I I OH OH cH, cH, 1 (8) I Ph-C-CH, Ph—CH- CH, -OH | OH OH Ph-CH,~CH-CH, | CH-CH, st ax on cH, CH, I Ph-CH-CH,~CH, (0) Ph-C-CH,-OH T | OH H 4. C.H,,0 #2» g + ¢; (B) and (C) both give +ve iodoform test. Compound (A) is : (A) 4 (A) CHs-CH=CH-O-CHz-CHs (8) cH-f-0-cH CH, CH, (C) CHy-¢-0-CH,-CH, (D) None of these CH,on NaOH, HO 5. =o Product Product is obtained in the above reaction is : R 9 Q R (several hours) (Principal component of coconut oil) (A) R-CO2Na (8) (C) RCHO (D) None of these HO. OH PART - IV : COMPREHENSION Read the following passage carefully and answer the questions. Comprehension #1 ° ° (P< fi. LiAlHe O_ Paite a) (ii) E10D wn (R) 1. (P) and (Q) respectively are2 (Ris OH oD D 5 D OH OH ° oD op D H ‘° © (0) oo oD oD Comprehension # 2 Me \ a ae pp Het P= B28 (6) akaline 9) HO. , ¢) Na+ iq. NH, alkaline T EOH ©) amo) 32a The compound (C) is : Et, Et Et, (A) (B) (D) Both (A) and (B) HOH fe 42a The compound (F) is : Et, Et Et, (A) (6) =<" (cyet (0) Both (A) and (B) HOH ren 52a The compound (0) is Et et Et H: OH H: OH HO. H (A) H: ‘OH (8) Ho +H (C) x: OH —(D) Both (B) and (C) et Et Et 6a The compound (G) is Et et et H ‘OH H OH HO—}—H A) H ‘OH (B) Ho- H (C) Ht: OH —(D) Both (B) and (C) et Et Et 7. The compound (E) is (A) Two moles of Me” co. (C) One mole of (A) and one mole of (8) (B) Two moles of Me” coon. (D) No reaction.Comprehension #3 ‘Answer Q.8, Q.9 and Q.10 by appropriately matching the information given in the three columns of the following table. Column-1, 2 and 3 contains starting material, reaction condition and type of reaction respectively. | Column-1 Column-2 Column-3 CH;-C-0-G-CH, ie 0) it if @ KMnO« ) Oxidation Oo 0 OPh eo di) cula Q) Reduction 0) : ii CHy-C-OH (iii) Hs0* (R) Hydrolysis a) bu, ™ (Oo (iv) LiAIHs (s) Dehydration 8. Which of the following combination of reaction result in formation of an alkene. (A) (I) (iv) Q (B) (Ill) (i) S (C) (Ill) (ii) S (D) (Il), (iii) R 9 The only correct combination in which product gives position test with sodium bicarbonate is - (a) (il) Gi) P (8) (1) Gi) Q (C) (i) Gi) R CVI) DP 10. The reaction and condition which obey bimolecular nucleophilic substitution reaction with respect to tetrahedral intermediate is - (A) (IY) ()P B Mima (C) (lh Gi) R (D) (Ml) (i) S LL Kkercise.3 ———————— * Marked Questions may have more than one correct option. PART - 1: JEE (ADVANCED) / IIT-JEE PROBLEMS (PREVIOUS YEARS) 1. What would be the major product in the following reaction ? [IIT-JEE 2000(M), 1/100] pee eases Tine cata? 2. Hydrogenation ofthe adjoining compound in the presence of poisoned palladium catalyst gives. Me oh [IIT-JEE 2001(S), 1/35] me | (A) an optically active compound (8) an optically inactive compound (C) a racemic mixture (D)a diastereomeric mixture 3. 1-Propanol and 2-Propanol can be best distinguished by : [IIT-JEE 2001(S), 1/35] (A) oxidation with alkaline KMnO« followed by reaction with Fehling solution (B) oxidation with acidic dichromate followed by reaction with Fehling solution (C) oxidation by heating with copper followed by reaction with Fehling solution (0) oxidation with concentrated H2SO. followed by reaction with Fehling solution10." Assertion : Dimethylsulphide is commonly used for the reduction of an ozonide of an alkene to get the ‘carbonyl compounds [IT-JEE-2001(8), 1/35] Reason : It reduces the ozonide giving water soluble dimethyl sulphoxide and excess of it evaporates (A) Assertion is True, Reason is True; Reason is a correct explanation for Assertion. (8) Assertion is True, Reason is True; Reason is NOT a correct explanation for Assertion. (C) Assertion is True, Reason is False. (D) Assertion is False, Reason is True. Five isomeric para-disubstituted aromatic compounds A to E with molecular formula CsHsO2 were given for identification. Based on the following observations, give structures of the compounds (i) Both A and B form a silver mirror with Tollen’s reagent; also B gives a positive test with FeCls solution. (ii) C gives positive iodoform test. (iil) D is readily extracted in aqueous NaHCOs solution. iv) E on acid hydrolysis gives 1, 4~dihydroxybenzene. [NT-JEE-2002(M), 5/60] The product of acid hydrolysis of P and Q can be distinguished by : [T-JEE 2003(S), 3/84] ococH, HG P= Hom’ a= cH, ‘OcocH, (A) Lucas reagent (8) 24-DNP (C) Fehiing’s solution (0) NaHSOs ‘Amongst the following the reagent that would convert 2-hexyne into trans-2-hexene is [lIT-JEE 2004(S), 3/84] (A) He.Pt! O2 (8) He.Pd / SOP (C) Li/ NHs / CaHsOH (0) NaBHs ‘A compound P(CsH100) reacts with dilute sulfuric acid to give Q and R as the final products. This reaction is about 10" times faster than of ethylene. Both Q and R give positive iodoform test. (a) Identify the structures of P, Q and R. (b) Rationalize the extraordinary reactivity of P. [NT-JEE-2004(M), 2/60] Match each of the compounds in Column | with its characteristic reaction(s) in Column II. i [UT-JEE 2009, 8/160] Column 1 ‘Column tl (A)_| CHsCH2CH2CN (p)_| Reduction with Pd-C/Hz (8)_| CHsCH2OCOCHs (q)_| Reduction with SnCia/HCI (C)_| CHo-CH=CH-CH:OH | (r) | Development of foul smell on treatment with chloroform and alcoholic KOH. (D)_| CHsCHACH2CHaNH2 | (s)_| Reduction with diisobutylaluminium hydride (DIBAL-H) (t) [Alkaline hydrolysis With reference to the scheme given, which of the given statments(s) about T, U, V and W is (are) correct? 9 (7) chy [IT-JEE 2012, 4/136] | LiAIH, CrovH (CH,CO),0 velOHH" WU _(CH.CO)O, (A) Tis soluble in hot aqueous NaOH (B) Uis optically active (C) Molecular formula of W is Cio HieOs (0) V gives effervescence on treatment with aqueous NaHCOs1. 12. 137 The number of optically active products obtained from the complete ozonolysis of the given compound is: CH, H | | |=CH-C-CH=CH-C-CH=CH-CH, (JEE-2012, 3/70] CHC H CH, (A)o (B)1 (c)2 (D)4 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, 3/120] Reagent(s) which can be used to bring about the following transformation is(are) : [JEE(Advance)-2016, 3/124] Ox, Oy COOH COOH (A) LiAlHs in (C2Hs)20 (B) BHs in THF (C) NaBHe in CHsOH (D) Raney Ni/H2 in THF PART - Il: JEE (MAIN) / AIEEE PROBLEMS (PREVIOUS YEARS) JEE(MAIN) OFFLINE PROBLEMS But-1-ene may be converted to butane by reaction with : [AIEEE-2003, 3/225] (1) Zn-HCI (2) Sn-HCl (3) Zn-Hg (4) Pde When CH2=CH-COOH is reduced with LiAIHs, the compound obtained willbe: [AIEEE-2003, 3/225) (1) CHs-CHe-COOH = (2) CH=CH-CH2OH (3) CHs-CHz-CH2OH (4) CHs-CH2-CHO. Which one of the following is reduced with Zn, Hg and HCI acid to give the corresponding hydrocarbon? [AIEEE-2004, 3/225] (1) Ethyl acetate (2) Butan-2-one (3) Acetamide (4) Acetic acid The best reagent to convert pent-3-en-2-ol into pent-3-ene-2-one is IAIEEE-2005, 3/225] (1) Pyridinium chloro-chromate (2) Chromic anhydride in glacial acetic acid (3) Acidic dichromate (4) Acidic permanganate The hydrocarbon which can react with sodium in liquid ammonia is: [AIEEE-2008, 3/105) (1) CHsCH2C=CH (2) CHsCH=CHCHs (3) CHsCHat SCH2CH3 (4) CHsCH2CH2C=CCH2CH2CHs In the following sequence of reactions, the alkene affords the compound ‘8’ -—_—[AIEEE-2008, 3/105] CHsCH=CHCH; —°-> A eS B, The compound B is : (1) CHsCOCHS (2) CHsCHeCOCHs (3) CHsCHO (4) CHsCH2CHO One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a molecular mass of 44 u. The alkene is : [AIEEE-2010, 4/144) (1) propane (2) 1-butene (3) 2-butene (4) ethene Ozonolysis of an organic compound gives formaldehyde as one of the products. This confirms the presence of : (1) two ethylenic double bonds (2) a vinyl group [AIEEE-2011, 4/120] (3) an isopropyl group (4) an acetylenic triple bond10. 1. 12, 13. 14, 15. 16. 2-Hexyne gives trans-2-Hexene on treatment with [AIEEE-2012, 4/120] (1) PtH (2) Li/ NH (3) Pd/BaSO« (4) Li AIHs In the given transformation, which the following is the most appropriate reagent ? [AIEEE-2012, 4/120] ‘CH=CHCOCH, CH=CHCH,CH, LT ee HO: HO 8 (1) NHeNH2, OH (2) Zn-Hg/HCl (3) Na, Liq, NH (4) NaBHs ‘Compound (A), CxHsBr, gives a white precipitate when warmed with alcoholic AgNOs. Oxidation of (A) gives an acid (B), CsHeOs. (B) easily forms anhydride on heating, Identify the compound (A). [JEE(Main)-2013, 4/120] CH,Br CH,Br CH, ‘CH,Br “ oO aOr @) oO Br ‘CH, CH, CH, The most suitable reagent for the conversion of R-CH,-OH -> R-CHO is: [JEE(Main)-2014, 4/120] (1) KMnO, (2)K,Cr,0, (3) Cro, (4) PCC (Pyridinium Chlorochromate) In the following sequence of reactions : Toluene —P._,q 0%, p tPA, the product C is : [JEE(Main)-2015, 4/120] (1) CH,COOH (2) CHxCH,, (3) CgHsCH,OH (4) CH,CHO The correct sequence of reagents for the following conversion will be: [JEE(Main)-2017, 4/120] 9 HOW_-CHs O- Ho-F-CH, CHO CHs (1) CHsMgBr, H'/CH:OH, [Ag(NHs)2]*OH- (2) CHsMgBr, [Ag(NHs)e]"OH", H"/CHsOH (3) [Ag(NHs)2"OH-, CHsMgBr, H*/CHsOH (4) [Ag(NHs)2]"OH-, H*/CH3OH, CHsMg8r The major product obtained in the following reaction is [JEE(Main)-2017, 4/120] DipAL-H COOH OH OH ay ao 2 OAs @) a gee wore CHO 00H ‘CHO COOH The trans-alkenes are formed by the reduction of alkynes with [JEE(Main)-2018, 4/120] (1) Nafliq. NH3 (2) Sn- HCI (3) He-PdIC, BaSO, (4) NaBHJEE(MAIN) ONLINE PROBLEMS The reagent needed for converting Ph H ; ; er Neze( ie [JEE(Main) 2014 Online (11-04-14), 4/120] HZ” “Ph (1) Cat. Hydrogenation (2) HelLindlar Cat (3) LiINHo (4) LiAIHe The gas liberated by the electrolysis of Dipotassium succinate solution is : [JEE(Main) 2014 Online (11-04-14), 4/120] (1) Ethane (2) Ethyne (3) Ethene (4) Propene Bouveault-Blanc reduction reaction involves: [JEE(Main) 2016 Online (09-04-16), 4/120] (1) Reduction of an anhydride with LiAIH«. (2) Reduction of an ester with Na/C2HsOH. (3) Reduction of a carbonyl compound with Na/Hg and HCl. (4) Reduction of an acyl halide with H2/Pd. The reagent(s) required for the following conversion are: [JEE(Main) 2018 Online (15-04-18), 4/120] OH E10,C. 02H a A H.C ‘CHO (1) () NaBHs (i) Raney Ni/He (iil) HsO* (2) (i) LiAIHs (il) H30* (3) (i) Belt (ii) DIBAL-H (ii) HsO* (4) (i) BaHts (ii) SnCle/HCI (il) HO" The main reduction product of the following compound with NaBHs in methanol is [JEE(Main) 2018 Online (15-04-18), 4/120] 9 9 Crew OH O OH O "” cr @) cr OH o 9 @i co ® NMez When 2-butyne is treated with Ha/Lindlar’s catalyst, compound X is produced as the major product and when treated with Na/lig. NHs it produces Y as the major product. Which of the following statements is correct? [JEE(Main) 2018 Online (15-04-18), 4/120] (1) X will have higher dipole moment and higher boiling point than Y. (2) Y will have higher dipole moment and higher boiling point than X. (3) X will have lower dipole moment and lower boiling point than Y. (4) Y will have higher dipole moment and lower boiling point than X. The major product formed in the following reaction is: [JEE(Main) 2018 Online (15-04-18), 4/120] OCOCHs ree exci cotcoworat) Sm Het OH(1) (2) OH ° 9° (4) HO. ‘OH 3 [JEE(Main) 2019 Online (09-01-19), 4/120] (3) RCHO (4) RCOOH 9. The major product ‘X’ formed in the following reaction is: [JEE(Main) 2019 Online (10-01-19), 4/120] OH H OCOCH; @ > OH H 8. The major product of following reaction is : RCN Sima 5 (1) RCONH2 (2) RCH2NH2 g 1 -H2-C-OCH3- a, x ron 1H H2CH20H ” ° OH tl H2-C-OCHs (3) 10. The major product of the following reaction is: CHiN Nast, aor 44. The major product of the following reaction is: OH H2CH20H (2) ° 9° [JEE(Main) 2019 Online (10-01-19), 4/120] HH @ orn Wa OH (4) CHIN AAA [JEE(Main) 2019 Online (11-01-19), 4/120] -COCHs ee (kMn04 Kota cH (W)H,SO, (ai) COCHs 0 I HOOC COOH ae: HOOC’ OOH or OHC: COCOOH 4) aa HOOK12. The major product obtained in the following reaction is : HH S {ecats ) CHs NO2 OH IH OH © ce. (@) eon NH: OH NO2 OH 13. The major product of the following reaction is : _t)DBAL-H ~wno Hes a9 oe : le 14. The major product of the following reaction is : Naw “ @ & ‘OEt [JEE(Main) 2019 Online (11-01-19), 4/120] OH OH S NHo OH NH> OH [JEE(Main) 2019 Online (12-01-19), 4/120] CHO CH=NH (3) oe “Se ‘CHO [JEE(Main) 2019 Online (12-01-19), 4/120] HH 1H oO a ‘OELAasves EXERCISE - 1 AA. A3. A, Ba. B2. PART -1 (a)Butane — (b) Butane —(c) Ph-CH>~OH (a) “K)<« HA (@) CHe=CH-CH»-CH2-C=C-CHs 225°) CH,-CH,-CH,-CH,-CH,-CH,-CH, CH=CH-CH-CHX CH, (b) CHe=CH-CH>CH2C=C-CH» —H/Pa-BaSO. . . Sect, (cis isomer) (c) Benzaldehyde (Benzene carbaldehyde) COOH (0) CHs-CHs-CH = CH(CH2))-CH2-OH (ii) (i) Ho/Pd-BaSOs (i) In this conversion ~CO- converts into -CHz~ which can be achieved by any one of the following reagents : (a) NH2-NH2/KOH/A (b) Zn-Hg, Cone HCl, A (c) Red P+ HI LiAIHs and NaBHs both gives same products with carbonyl compounds. (i) Ph-CH2-OH LAD Iolowed HO om Fog bon, ba HH UAH. folowed by D0 og |p HAW followed byD.0 on ocr, i i bo ° NaBO followed by E1OH,. py! on, i ba ° DuPt L_om yn fog ib oO OH _/OH (a: 1H OH HO- e. HO- (ii)a: ib HO“ cH, HO “cH,B-3. C2, 3, Da. D2. D3. oO @ (b) O _Rapow fa CHO () CHsCHe G-GCH.CH.CH, (ii) CHsCH2COOH + HOOCCH2CH.CHs H,-CH, (OOH Hs :00H @ toto, (b) en. o H Cold dil. KMnO, IH KMn0, eas —s ©) etn. @) i COOH (1) Peracid (2) H,0° “OH t-Butanol is not oxidised by dilute KMnOs, so it does not give brown-black precipitate of MnO2. n- Butanol is oxidised with dil KMnO« and MnO.-is converted to brown-black precipitate of MnOz. Me Me. OH_DLKWnO. No reaction Me -Butanol Moon |—DLWomnO. _, CHsCHzCH2COOH + MnOz 4 (Brown black ppt.) + 2KOH + 2H20 n-Butanol (a) oe: °° (b) 2 HCHO + 2 HCOOH (c) CHsCOOH + CHsCHO 2 5 OH 7 os oy Hooc ° CHO O HO" oO cura CulA (@) Ph-CH,-CH,-OH "> Ph_cH-CH=0 (b) Lele coals eee Ly od OH cH, I (c) P-G-O8 ous ph ou, bawon Ka E4. £2. (a) CH-CeN—*O 5 H,cooH (o) cHwnc 22 > cH, + HCOOH E-3. CHsCOCI E-4, CHsCOOH + NHs E-5. Two carboxylic acids NH, Es. E-7. CHa=CH-O-CH3 NO, PART-II At. (A) A-2. (8) A3. (B) A-d, (D) A-5. (8B) A6. (B) A7. (0) AB. (A) Bt. (B) B-2. (A) B3. (C) B4. (8) B5. (A) Bs. (B) B7. (0) ca. (C) C2. (C) C3. (C) C4. (C) C5. (8) D4. (Cc) D2. (C) D3. (C) D-4. (B) E4. (0) E-2, (C) E3. (D) PART - Ill 1. (A) — (q) : (B) — (8) (C) -(P, s); (0)- (4, 8) 2. (A) - (p) | (B) - (a): (C)- (t) ; (D) - (s). EXERCISE - 2 PART -1 1. (D) 2. (0) 3. (0) 4 (B) 5. (Cc) 6. (D) te (D) 8. (D) 9. (D) 10. (A) PART - I i 3 2% 3 3 3(ii,iv) a4 3 SF 6 4 (iii, v) PART - Ill 1. (ABCD) 2 (AB) 3. (AD) 4. (BC) 5. (AB) PART - IV 1. (D) 2. (c) 3. (A) 4. (B) 5. (A) Cn) 7 A 8 §=(C) 9 (D) 10. (8)EXERCISE - 3 PART -1 CH CH, 4 ue real H & (B) 3. (c) 4 (A) OCH, OH OH cH, OH 5. (A) (B) (c) (D) (E) CHO CH,CHO COCH, COOH O-CH=CH, 6. (c) 7. (c) - fe 9 ys 8. (a) P= qo sas :R=HO-CH He” i SCH, hes Ncu, ci or aad W 9 pots P= :Q= :R=HO-CH ne? SCH, He SoH, (b) The greater stability of the oxonium ion intermediate is responsible for the extraordinary reactivity. This is demonstrated for the two sets of P, Q, R (cases i and ii above) as follows. W We p—N — “No wg —+» ANN 9. (A)-p.q,8,t; (B)-s,t ; (C)—p 5 (D)-r 10. (ACD) 11. (A) 120«5 43. (CD) PART - Il JEE(MAIN) OFFLINE PROBLEMS 1 a) 2 (2) 3s @) 4 (1) 5s (1) 6 (3) 7 (3) 8 (2) % 2) 10. (1) 14. (4) 12, (4) 13, (4) 14. 4) 15. (4) 16. (1) JEE(MAIN) ONLINE PROBLEMS f. (3) 2. (3) 3. (2) 4. (4) 5. (1) 6 (1) 7% (3) 8% 3) % 3) 10. (2) a = 2 © “m=