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    "} é¢ 2-2 2 o a ee Aa at a a oat ree b bt TTY b FOC CCCP OCC dd dd J 6 wees | ie GENERAL ORGANIC CHEMISTRY Rules for writing Resonating Structures Allresonating structures must be valid Lewis structure, ie., a carbon, N or © can't be pentavalent @ H cant be divalent etc, (6) Positions of atomic nuclei and s-electrons remain constant, Resonance is all about x-electron delocalization, therefore position of x-electrons and non-bonding electrons may change in various resonating states. Invalid resonance states for benzene because distance between two carbon atoms are changing in these structures, All the resonating structures must have same number of unpaired electrons (Lie, An = 0) © For the effective overlap of portals part ofthe molec taking part in vesomance must be planar @ Stabitity of alkenes can be explained by hyperconjugative effect. He Hy CH, HO Ho HG CH, =CH,< Np=oiy< Ne mt < PeC < -~ ye He We Mon? ay He7 cH, Increasing order of stability with increasing number of hyperconjugative structures AROMATICITY Aromaticity: Its explain the extra stability of cyclic molecule, It do not give unsaturation test like Baeyer’s reagent test and bromine water test. © It do not give electrophilic addition reaction. . Tt contains diamagnetic ring current. © It shows electrophilic substitution reactions. Aromatic Character: [The Hiickel (4 + 2) rule] . The following three rales are usefal in predicting whether a particular compound is aromatic or . 1on-aromatic. 1. Aromatic compounds are cyclic and planar 2, Bach atom in an aromatic ring is 9p? hybridized. ; 3. ‘The eyelc m molecular orbital (formed by overlap ofp-orbitl) must contain (4n-+ 2) electrons, forth Delhi: 72, Mall Road, GTB. Nagar, New Delhi ~ 110009 + South Dethi: 28-B/7, Jia Sarai, Near IT, Have Khas, New Delhi - 110016 + Pir: O11-41415514, 09136597244, Toll Free; 180-200-4940 Heb.: wwrw.chemacadeniy.in >, CST ie, 2,610, 14... nelectrons, Where n= an integer 0, 1, 2,3, .. Relative St y of different Carbocation Stability of different types of carbocations in decreasing order bt = > éu-<] > ‘) > (caip,t> caine (CHL),C ® a e 9 @ ® lls CH 2CH; = CH—CH, > CHy—CH, > CH, > CH, = CH> CH =C EXERCISE -I Single Correct Type Which of the following is the strongest base in water? . @ td ® Co “ Oe) H H 1 On monochlorination of 2-methyl butane the total ‘number of chiral compound is (2 ()4 6 @s Which of the following is most basie in aqueous solution? NH NH I CH, CH, 1 ¢, | (a) HN7 SNH, (6) CH—-N—H (©) CH —-N—CH, (A) o7 Sty The most stable free radical is “cH o ® 6 of 00) ‘Which ofthe following double bond in the given molecule is most reactive towards a strong protic acid? ce eagaaagnas nn eee ANT AArn? ee ee ee ee ee ann ann? erases 660066 66666 dod dd d-d_6-6_ dudes. A | IETS © Arrange the given carbon acids in the increasing order of acidic strength Of orf (@AI>0 onan (Oll> 1 (@Oil>M>1 For which of the following reactions equilibrium constant (k) is less than unity? (@) (CD),C—H+ (CH,C’ == (CD,),C* + (CH,),C—H o) O sth O- cH, (©) cH—C=C—H + NH CH,—C=C: + NH, @ O «li (O> +iNH, Which of the following compounds yield most stable carbanion after rupture of (C,-C,) bond: 0 0 ° | Il I) (a) CH,-C-CCI, (b) CH, -C-CBr, OF a (@) none of these 12 12 2 In which of the following molecules the lone pair of nitrogen atom is participating in resonance? CHS. 70H CHIH, CO @ or re “0 ox Which of the following incorrectly represent the acidic strength of given acids? (@ CCH > F,CH (b) CH,COOH > CH,CH,OH OH OH (©) H,0 > CH,OH @ 0 > oO NO, 1 16. 17. 18. EAE aera || 4 13. Which of the following incorrectly represents the stability of reactivity intermediate? + eo (a) CH.-CH, o SCH? < cre NO, CH, Which of the following can exhibit geometrical isomerism? =N-OH () o> HAH (©) (CH,),C=C(CH,), @ IN e 14, (@) GHC 5, The avid strength of substituted carboxylic acs is known to be depentlent on the nature and position of the substituent. In the following examples, an attempt has been made to arrange the acids in ord of acid strength, the strongest first. One of the series is incorrect-which one? (a) CHyCH,CH(C)),COOH > CH, CH(C),CH,COOH > CH,.CH, CH, COOH (b) NO, .CH,,COOH > HOCH, COOH > CH,,COOH (c) CkC.COOH> BrCH, COOH > FCH, COOH (d) CH,.COOH > CH, CH, COOH> (CH.),C:COOH Which of the following molecule is expected to have the greatest resonance stabilization ? o( 1 of OOOO «bd Which of the following is most pola Which of the following is aromatic, A as (@) OC © Oo © a @ (Ginglt eb) ; LZ © c G G & TC « —_l 19. 20. 21 22: 23. 24. Coenen eee ‘What value of n in Huckel’s rule applies to the aromatic compound shown below ? \ , YY 3 (4 5 (9 Correct order of stability of carbocation given below is : a ® ® A me qu ct, -CH-CH, (y) CH, =CH @U>M>I>1V (byI>n>MaIv @M>1>M>Iv @I>il>ie tv ‘Which of the following species is most stable ? @ ° (0) p-NO,—C,H,CH, (b) p-C-C eH, — CH ® (@ p-HjCO—CoH—CH ® (©) CoH —CH, Which of the nitrogen compounds shown below is the strongest acid ? 9 QO °o™ “Oe “OLY “OL 0 0 9 Which pair will not form a stable carbocation ? C-ax0 tL (a A WANG (a) Land II (b) and IT (o) Wand IV (@) Mand IV Out the following isomeric compounds, which one would give three constitutional isomers, (one of which possess a stereogenic centre) upon monochlorination ? (a) CH,CH,CH,CH,CH,CH, (b) CHy ae a CH, CHy ‘a (6) Cs ~CH- CH, -CH, @ ae I i cH, -CHy 2 CL AA q cH, @) Ni 2s 4 HM PhNH g= a Correct order of basicity is (@)3>1>2>4 () 3<124 ()3<4<1-2 (@)3>4>1>2 Which carbocation is least likely to form as intermediate? @cune wl ye of @ cH, —CHy ‘Among the following pairs in which case the second eompound has higher heat of hydrogenation 26. 27. @) QO (b) Cis-2-butene, trans-2-butene oO | (a) I-butene, 2-butene 8. 0) Ds which is not correct about (1) (a) 1 istmore soluble than bromocyslopropane (b) [gives pale yellow ppt. on addition with AgNO, (6) shaving lower dipole moment than bromocytlo propane Be (d) have more ionic character than ‘Which one of the following has the smallest heat of hydrogenation ? (a) |-Butene (b) trans-2-Butene _(c) cis-2-Butene (d) 1,3-Butadiene In the following compounds: Jo Q)I>IV>I>0 @M>i>M>V @IVvetb>Pt lowing, the most basic compound is: PCH NH, (€) m-NO,-C.HNH, (4) CQH,CH,NH, AANA NAO MS 5 neroeogs nnn i jae Ce | I ‘Arrange these hydrocarbons according 32. Selected bond angles for six hydrocarbons are shown below. to their pK, values, from the lowest to the highest. fo” Se & the a Oe ()V<1y>z (b)x>z>y (y>x>z @yr2>x | Delhi: 72, Mall Road, GTB, Nagar, New Delhi 110009 * South Delhi: 28-B/7, Jia Sarai, Rann eess New a ee a arenas nesarcirr gd Toll Pena: TE; 200-4040 RS: Wee y i‘) = Ol y my | ° ll ee 36. Consider the hydrogen stom etached to three diferent earbon atoms Cabeled 1,2 >) Ras = . attached hydrogen atoms in order from most acidic to least acidic a ALS a 1 1° e 12 e (@)2>1>3 (1>2>3 (2>3>1 (93>271 37. Which ofthe following compounds would you expect tobe strong carbon aci@? 5 . a . i, \« @ pion ©) (cHycoe), @ CH,COCH,COOC,Hs | 0 38. Arrange the following compounds in the increasing order of acidic strength. | (i) benzoic acid (ii) p-methoxybenzoic acid (iii) o- methoxybenzoie Aci \« (@) iH>M>1V @U>iv>I>M ()ll>I>Iv> @Iv>i>1>m Which is the strongest acid among following (@)CHCN), (0) CHYCO,Et), —_(¢) CH,ON (@HC(CE,), PhNoa is more stable than RN» because (@) in PRN, +ve charge undergoing delocalisation inthe ring, (b) Ph having -I effect whereas R having + effect. (©) in Ph group carbon is more electron defficient wart. carbon in R group, (@ all ae incorrect —_ eg ei ll ar 49, Column-I (Carbanions) ot a ‘ ¥ (A) 0 @ 43*10%s a ’ Hcy “Cas coe a, e ‘ o ®) (Q 25x10%s NO, fis © Cy (BR) 87x107s ty © | (S) 14x 104s He 2 @ Ce EOE -Q),(D-P) () (AR), B-Q), (CS), OP) ()(A-S), aoe ce Line AQ (B-S), (CP), (D-R) of the highest Q O is following 2 . © @) OO ai a, 66.46 6.6 66.4. id J. 5: 55. 56, 37. CT ll 3. Which of the following second one has high Resonance energy OQ 0.00 OO, O @ OO. os »O*-O<3-0- »On-Gn0-V © Y9.6 O)-(O (d) None of these Which of the following is not example of cross-conjugation 9 “CY CO 07 = OAs @ Oo Which of the following compounds have no delocalizeds electron H,C—CH, U\ A oO oF oOpawmO neacret H a Energies of three resonating structures of a compound are E,, E,& By respectively and energy of real molecule is E, . IfE, > E, > Ey then the resonance energy will be: (@) (E+E, +E,)-E, ()E,-E, LC © ll 58. The abstraction of proton wil be fastest, in which carbon in the following compound, o y x 2Avn hoo @x ®y @z @p 59. Which of the following have highest resonance energy. ol ©) y. ol J o | H 60. Which is more basic Me HH , I hs ae, | HN NH we A B 61, For phenol which of the following resonating structure ‘is the most stable? @ g. e. or i (@ > ) O 6} Oo (a) All have equal stability 9 ® GP o SS © 0-0-0-0.-0 N on N N N 1 9 9 9 v Il it Iv Among these canonical structures of pyridinie, the correct order of stability is, (@(I=v)>@=1v)> (@=1y)> C=) > (@(=V)>Ill> =I) (o> @i=1V)> d=V) 63. The homolytic breaking ofthe C, ~ C, bond is easiest in: Be EG ho BG Pi ae olac-k wtp at oF RX OF ha ycdi H CH CCH HC CH; ai 1009: Suh Dei: 20-57 Jari, Nor He Kas, New 36597244, Toll Free: 800-200-4940 Web. : wnchemacadeaniit GOCUVCdCdY ll em 6. 65. 66. 67. 68. 69. a | ‘Write the decreasing order of reactivity towards electrophilic addition. + oH oe, UC; . Ar ne ae wc a ue » m SI Bg x, “ o ut w uy @U>M>IVv>1 @)m>n>1>1V (@I>n>m>1V (@) I> i> n> Vv Write correct order of stability gy ae de dys Sayan wee @IPU>M>V @)M>I>I>IV |M>I>1>1V (@)M>U>tv>1 Which of the alkene has least heat of hydrogenation MC FB WG CHC HC OCH, HG @ © © ss leat H oH TEC ye CHa mG seen Hy Which has least heat of hydrogenation o/——\ 0 — oo a == ee Say we Asx n, Hess yy 4 Sy :-} Yis CH; CH; CH, | (@) cir ) Te C—CH, bw CN CN CH; CN [ (©) CH;—C_CN (@ CH, H tx ‘Write correct order of reactivity of following halogen derivatives. a o (1) CH,-CH-Cl_ (MM) Et,C-Cl (IV) PRCH,CL —(V) Ph,C-Cl (@I>V>Iv>m>n @V>IV>I> Mon ()V>I>IV>IP I (@1>V>Ml>Iv>n . Nagar, New Deihi - 110009 + South Delhi: 28-B/7, Jia Sarai, Near UT, Haixz Khas, New -Oli-41415514, 9136507248, Toll Pree: 1801-200-4940, Web, wwwnichemacadeny,in Delhi - cnemacapeMy a so f 10. ce cum erento ons oO sg in column-I1. r Column-a (stability) Column-II (Reason) r ae S @ o > CHS (®) Inductive effect fos 8) ee (Q Resonance © BK, PHC cH (R) _Hyperconjugation : oommianaai ea ne of following carbonyl compound when tre oO i Te oor-tcn, o a ch Se hae |e 1a | | OI 73. Arrange the following in the increasing order of their basic strength iE O 1. OC OL. O WV. Co (@IP>T>S ()T>P>R>S (R>T>P>S (d)P>R>S>T Write the correct basicity order of the following compounds. t { { o(e oy mi) ols @)I>I>IV > Q)I>I>M>IV. @ISIV>MHIv (> UI TV>1 Which of the following, has the most acidic hydrogen? Ov: (a) 3-hexanone —(b) 2, 4-hexanedione (c) 2, S-hexanedione (d) 2, 3-hexanedione Which of the following is the correct order of acidic nature. 0 ® a a x (a) M>1>11 (I> U> mm (QU>I>m (QUl>n>1 The correct increasing order of Ka of following acid. () CH,CH,COOH (ii) CH, = CHCO,H (i) HC=CCOOH @d<@) Br + uw | H il vi ai al ai @* . o* o* @* Reaction coordinate Reaction coordinate Reaction coordinate Reaction coordinate 89. Weakest base among the following is : @ [ye ome OCH @ Cs 90. Rank the following in order of deoreasing basicity. (ts call eh tly hie (Wy) A? (@IV>I>M>T ()I>IveN>M = @l>l>m> (gens 91. Correct order of basicity is: Wh Ny NH NH, @ O oO) wo) ayy om ‘Me Me (QI>0>MI>1V ()I>1>1>IV @)M>M>1>1V @M>Ml>tvet 92, — Write the pK, order of the following acids, ac. ial cea a (O)x>z>y (e)z>y>x (dy>x>z ‘Which of the following is the correct order of basic nature, OY OO 0 GH Of ig @)Q>R>P (W)R>Q>P (@R>P>Q | “+ North Deli: 72, Mal Road, GTB, Napur New Delhi - 110009» South Deli: 28-87, ~ Delhi= 110016 ae (09136597244, Toll Fre: mon ogrtek TTS 94. The compounds that react with aqueous NaHCO, to release CO, are 9 rs 7 ee Pr 0, 9 HOY Sy Se O20 a oul @ he! q@uowc \— Ho =O Ho © OH os HO ‘OH ; (a) Land3 (b) 2and4 (c)2and 3 (@) 1 and 4 95. Correct order of bond strength of X-F in following compounds/molecules. (@B-F(BF,) (il) C-(CE,) Gi) N-FONF,) O-F(OF,) (¥) FFE) (0) iY>X . hg cuencxcapey TT Geral Orzanis Chemisty] 97 i01. Match the following a Column 1 Column Tl (DOU) a ° (Degree of unsaturation) » (A) Azulenie ®) 4 a> (B) —Napthalene @ 5 . © retain CI) ® 6 as! () 1,23: cyclo propyl eyclo propane 7 i (2)(A-8), (B-8), (C-Q),(D-P) (6) (A-), (8-8), (C-P), O-R) & (¢) (A-8), (B-R), (C-Q), (D-P) (d) (A-Q), (B-P), (C-R), (D-S) j Ny) 102 Comeet order of acide strength ofthe following compound is ~ Oo 0 AD Oy ~yo o 0 Cao) @ 1) Hi} ke woe & aed . oy ae ) ue Sas @I>IV>>M (b)IV>M>I>M (I> 1>Iv>m @)IV>T> >I 103. Which one of following represents different molecules? P o 2 I (Me) 5) Cm OHH, Product 9, oH Oca, © On OH OH = | | Ph \ i (@P-CH-Ph@ Ph—CH-Ph © hE oon Pho Ph 105. Arrange the following compound, in order of C-N bond length. Me “ "Oo ® om © Cu. e “Oy" sagt NO, NO; ()D>C>B>A__(b)D>C>A>B_()A>B>C>D @)D>A>C>B AIT Hatz Khas, New Sarai. wwnchemacademy.in 106. The correct order of boiling point is: 6 6.6 & NO; @ @ ®) © (@P>Q>R>S B)S>R>Q>P )S>PPQHR @P>Qrs7R 107, What will be the order of rotation bartiers about C-N bond among these compounds ? A Cs TS | 7 e sl Lak (1) CH,-CH,-NH, 0) yy a cag Ne (a)1> > HL (by 1<1m>1 (@M>I> gO, oto). o a ay ‘Arrange these compounds in basic strength order: (a) [>> (by t>1> (glll>i>n 109. Followi ins three C=C, i (le Wt so b>c>a (b)a>b>e (c)b>arc (@c>b>a ‘Which of the following hydrocarbons has the lowest dipole moment? -2-butene _—_(b) 2-butyne (©) L-butyne (@)H,C=CH-C = CH (3) CH,CH,CH,COOH (b)3>1>2 (e)1>3>2 (@3>2>1 carbon ie radial is most stable (GH -CH=CH, (HCH (@)CH—CH-Ph | | TT i 9 14 cH BuScHV/AIBN product =F pn i c : 4 HO HO H > eal I a oc @all | . be a : Me cH, ~ CH,-CH—C— = 8} ous. : c i , Nie _ 1. (x (major) tt CH, CH, “2 rs bi = ale 2 —— @ Px “3, ae ‘ a. iN, Nan a 2 116 Sa PI 2) ee Hy-Cl HH gH,-NO, 17. ey “a0 OD leq)” Major product of this reaction at 40°C is: CC || = os | OH 118, D HE YX 5 on OH OH “(OL oy © cx @ Of fi 119. Give rate of dehydration when given compounds are heated with cone, H,SO,. ve HL o CHO CH b Hy - ol) @ ®) ) a "i (@R>Q>P>S ()Q>R>P>S (R>Q>S>P ()R>P>Q>8 , ’ o 120. CH,=CH-CH,-CH,-CH,-CH-SH eh "HE | EE 122. Pick the correct statement for monochlorination of R-secbutyl chloride. (a) There are four possible production ; three are optically active one is optically inactive (b) There are five possible production ; three are optically inactive & two are optically activ (c) There ate five possible production ; two are optically inactive & three are optically active (@) There are four possible production ; two are optically active & two are optically inactive COCCbCeYG = 123, Possible products formed during the reaction. A Allyl Na (Dry ether) cus SCH, -Cl © { | 124. Statement-1 = The major product formed by the electrolysis of aqueous solution of IK Alia opti uti COO} K Statement-2 : The product has C, axis of symmetry. (a) Statement-I is true, statement-2 is true and statement-2 is correct explanation for statement-1 (b) Statement-I is true, statement-2 is true and statement-? is NOT the correct explanation for statement-1. VS BOSCCeCSCECeCCdéeed (c) Statement-1 is true, statement2 is false. (d) Statement-1 is false, statement-2 is true. EXERCISE - II Multiple Answer Type CHCOOH i (maleic acid) can show : bacon ‘ (a) stereoisomer (b) geometrical isomer (©) chain isomer (@) functional isomer 2. Which of the following compound(s) can show tautomerism ? t ot (i) CH,-C=N (O)C-O% of Bi «North Dethi: 72, Mall Road, GTB. Nagar, New Delhi - 110009 + South Delhi: 28-87, Jia CL | eS 3. Which lone pairs of nitrogens in the following molecule participate in delocalization? i (@)W OX @zZ io = 4. Whieh ivare fess acidic than Benzoie acid? = af COOH (@CH,COOH ®) (Opcoos Qe (a) 4,0 {3 & I NO» on 5. Which have active methylene group? = id " (a) CH, -C-CH, -C-cH, () CH,-CH,-NO, = = - 9 9 g © cH, bca, lias (Oy Len,-e8 CLC) = || (@) I & 111 are antiaromatic (0) 1 & IV are non-aromatic (c) Il alone is aromatic (@) 1& IV are non-aromatic 9. Which of the following have acidic hydrogen? C-CH,-CN — (d) NaNH, r (a) CH,COOH ® (O)-on (© cH. 10. Which of the following may be classed as an electrophilic reagent? (@) BCI, ()) NHS © ca, @ Alc; 11. Which of the following would not have a dipole moment? OH (a) CCl, (b) CH,Cl, (c) trans-1,2-dichloroethene (d) 12. Which of the following compounds can exhibit keto-enol tautomerism? oO HC, cH @ 'b ee HC, ' c-0 Ce, 13, Which species is/are aromatic? (a) O (b) O 14. Aromatic character is possible only when (a) four electrons are delocalized (b) the molecule is cyelic and planar having delocalized (4n +2)r electrons where n=0, 1, 2, (c) alternate sigma (0) & pie (1) bond are present, (d) None is true 15. Which does not reacts with AgNO, to give ppt.? @) (0) Br © ‘Dethi - 110016 « Ph. 011-41415514, 09136597244, Toll Free; 1800-200-4940 Heb.: CA | RISTO 16. Which are correct statements? (a) methyl malonic acid is converted into propanoic acid on heating (b) succinic acid forms suecinic anhydride on heating (©) 4-hydroxy butanoic acid forms Lactone on heating re (@) CH, ~C-CH,COOH forms acetone on heating c 17. Select the stable molecule (s); 2 oe Nee @ Cr (®CCLCHOH, © ‘9 @ oo H 0 18. In which of the following the 2nd structure having more resonance energy: wl Jat CC || » | 21. Inthe given reaction ‘Hy eke) ae (a)can be as major product CH, CH: (a) y-CH=Cl (4 . (o) Sr . @ ie 22. A pyridine derivative (P) reacts with (Y). (¥) can be free radical, cation or anion, The structure of intermediate (Q) formed in reaction is given below (P) and (Y) respectively can be i Y Seeinetattent ae ue Ft CeCe oO 2 ¥ 6 A eC Se Se SE Re, ° % & & 23. Choose all alkane that give only one monochloro derivative upon reaction with chlorine in sun light of) worX oX K ow J) 24 Corret order of stability ofcabanon linked with Mg (a) Phenyl > Vinyl > Cyclopropyl (b) Methyl > Ethyl > Isopropyl i (©) Cyclopropyl > Vinyl > Phenyl (4) Bthyl > Methy| > Vinyl 1} 25. — Which of the following correct order of Resonance energy oO mee : Poi oo y ih CEES ao (@) None of these Which of the following i example of Tentormerssa i > Dre Oe @acen? nea ‘NHMe N-Me @p,cH-CR=NRR,C=CR-NER wae & give red colour with FeCl, solution TEEN OO ND Ye On, Jeon oy ele (gg A encased NH, ’ e Bs: Ce AE ETE a “me ~ NH, ‘ ZN Nh Nth -_~ Oo a. Oo 4 » 6 NH, » EP ~ NI) Nh © + EDS) @ SO OL c ¥ Eel MeO" ‘OMe OMe ¥ ae ; OM) 2 cH —cr,—C_oK + Products) “> (@) CH, —CH,—CH,—CH, (b) CH, = CH, 2 gs ° i @ CH, I) © CH,—CH,—C—CH,—CH, Which of the following reaction is/are involves carbon free radical as an intermediate 9 9 | i \ @® CHy-cH,-C-0K Besoin Cy CHC -OAag E> 0, ime a (9 ON 1 (@ CH, = cca, NO, Which of the following carbon free radical do(es) not undergo self-combination CH; Ph | HC | ae (@) Pho wie © @ aga I cH, 0 0 I CH;—CH,—C—O-—CyHs + oi, boc, MEM, Product(s) Qo 9° © cH,—cr, tb cu—cH, ci, on, 00 00 © o,-c1,-t-_cu, f oa (@) None of these EXERCISE - Hl Numerical and Subjective Answer Type 1. Number of 1-eleetrons in Cyclobutadienyl anion (C,H,)?> is, 2. Which of the following carbon will be deprotonatated first on treatment with a tia ve 3. How many litres of methane would be produced when 0.6 gm of CH,MgBris treated with excess of CH NE, 4. The number of moles of erignard reagent consumed per mole of the compound See . SH 9 ’ 5 8 ba aint v os gets) x oa ah C1 (iH0" OH jy Fe qeonangnnnrad¢ errr? = sane PIII NOON TTT 2) 2 2) 2) > » 2 9 2 » - 2 3 oo9 | | ETE on if Ph—-C-Ph a i (reaction-3) p0-U-0-8; Warigne, (reaction-3) wou" Ph What is the value ofx-+y+2~? 6. 4.6 g of'a polyhydric alcohol was treated with an excess of methy magnesium bromide to produce 3.36 litre of CH, at STP. Calculate number of -OH group present in the alcohol. (molecular weight of alcohol = 92) 7. How many moles of Grignard reagent can react with one mole of following compound. ey COOP O 2 « 7 4 8. Number of possible product on monobromination of the given compound is HO’ Me CHy SS NBS 9. Amongst the following, the total number of compounds soluble in aqueous NaOH (at room temperature) is S CH; OOH = OCH,,CH, HH NO, Cre OH CH,CH, ° 5 oy i ON 10. The total number of contributing structures showing byperconjugation (involving C —H bonds) for the following carbocation is HyC.@-CH,CH, North Delhi: 72, Mall Road, GT.B. Nagar, New Delhi - 1] 0009 » South Dethi: 28-B/7, Jia Sarai, Near IIT, Hauz Khas, New se UE ! > ETT soe In above compound total number of 2° hydrogen atoms are: Cost “OO ‘OH ny nyc-on NHC 5 (4) (B) Es (C4 (D) ¢ eat as il ‘Sum of molecular mass of gas (A + C) is f -c=ch 409 Ph-C-0-H—N#23_4(A) gas ae Hd Ph-OH—“2_4(C) gas R-0-H—4 4(D) gas ‘Sum of molecular mass of gas A+ B + C+D is: P.Q,R, Sand Tare the number of x electron in a, b, ¢, d and e respectively. What is the valuc of P+Q+Rt+S+T. | > | TT 18. Arrange the following in increasing order of stability. Hy )~CH =CH,» 0 “Cy? (regarding to stability of free radical) * 4 A : (b) oJ Lot Jeo CoQ (regarding stability of free radical) (@) (1) cH, =CH,, @é 9 6 Resonance energy of a is much lower than that “() but resonance energies of (j= o lL o. : are identical. Explain é¢ ee ee ee ee oe ee ee ae 2 ode ddddddidds 20. Ordinarily the barrier to rotation about a carbon-carbon double bond is quite high but compound have a rotational barrier of only about 20 K cal / mole ney ‘What is the reason for:this th (A) 21, Among the following compounds select those (i) Which will readily dimerise. (il) Which are Quasi aromatic a) @ cu %) O oO | Anule @ A Qs 2 aii How can you explain the aromatic nature of prophyrin? pbuddddd Delhi: ag i a hj: 28-B/7, Jia Serai, Near IIT, Hauz Khas, New ‘North Dethi: | Road, GTB. ‘New Delhi - 110009 + South Del : ; ee oe » ph OLL-ATALSSL4, 09136597244, Tol Fre: 1800-200-4940 Web wwrnchemacademy in m4. 25. 26. cp ES ha Di) «il a 23. Arrange the following in increasing order of pKa values 2 (@) ()HNO, (2)H,0 (3) HCO,H (4) CH;CO,H (5) PhOH iS w ®) (1) CH, (Q)PRCH, (3) PhC=CH (4) ees 3 ; 8 G (© Q)PKCH, @)cuccu-c-cs, (@)CF,CO,H (4) NH, c I 1 c 0 0 1 (@ ()PhCH, @)HCN 3) HCO,H (4) CHO cy Ni on Nt «| (1) NH, ocy (3) PhNH, (a) - Br al OH = ! on Ne @® @ (2)CH,=CH-OH 3) HC=C-OH 4) = Be = For the following compounds, arrange the labelled proton in increasing order of their case of deprotonation: - = p at «CH we re - @ cr wey © o ail, O14 an Hw we _ HH! yy? 9 Decreasing order of enol content of the following. (along with proper explanation). a s c wo BA 0K 0S oni oO OW \ve In which of the following pairs, indicated bond is of greater strength. 9 I Oe “ & “O° | c [ I OH On 18 EXERCISE - IV Previous Year Questions I1T-JAM Previous Year Questions 1. ‘The correct statement describing the relationship between oo 9 s7 Vg nae” RCN RO=N Ms \, RHC-N anes . me oe (a) X and Y are resonance structures and Z is a tautomer () X and Y are tautomer and Z is a resonance structures () X,Y and Z are all resonance structures (d) X, ¥ and Z are all tautomers 2. The correct order of acidity among Me @ ® W& @ aoe | iN H HOW ( or) a) ti) Fe 8 a me lS Torr |i (a) (0.<(t) > 2 ° 3 > > 9 8 | = | TOT The correct orientations of dipoles in pyrrole and hyridine is a Ot woe Ot Ot Ot .Ot Ot ‘The correct order of stability of the following carbocation is O-c oO 1 (a) I> 1>1 (b> m>1 (i> M>m @ T>Mel ‘The specics/compounds that are aromatic among the following are Hl e . j tN 1 corte cctinad P g R s (a) Rands (b) PandQ (©) Qands (d) Pand’S Hybridizations of the atoms indicated with the asterisk (*) inthe following compounds sequentially are CH 0-0 DD. ee me mi 0 as ia Re eS (a) sp”, sp?, sp*, sp? (b) sp?, sp, sp?, sp? (0) sp? sp’, sp*, sp (A) sp? sp, sp°, sp* ‘The product P and Q in the following reactions, respectively are cl f T CH _ nets p 1 “249 ES a ee : Too CO mo Benzene Dewar Benzene (2) Canonical forms (b) Structural isomers (¢) Taatomers (@ Conformational isomers “Azrange the following in the correct order of acidity of the hydrogen indicated in bold. oO (@P>Q>R (@R>Q>P ()Q>R>P @P>R>Q Arrange the following in the decreasing order of acidity of the hydrogen indicated in italics @.cH,cocH, (i) CH,COCH,COCH, (@ CH,OOCCH,COOCH, (iv) CH,COCH,NO; > @>O>W) ‘ (0)@)> > @> Phenols less acidic than MACADENN > Reece ‘The amount (in gram) of NaOH (MW = 40) required for complete neutralization of one mole of the following compound is ............ HOOC Ny ATE Previous Year Questions ‘The major product obtained in the following reaction is =C_CH,OH BUN @oniyrigntt, , ae LOH > ctisbr(lequir) 3.H,0* (@) CH,CH,—C=C—CH,OH (t) HC =C—CH,0CH,CH, (©) CH,CH,—C =C—CH,NH, (@) H-C=C_CH,NH—CH,CH, Among the following compounds, the one that is non-aromatic is @O wo of] ots recom ol) (a) Aromatic and has high dipole moment (b) Aromatic and has no dipole moment (©) non-aromatic and has high dipole moment (d) anti-aromatic and has no dipole moment 23. The compound that is NOT aromatic is S oO @ (@) () (@) © Ss S O : 24. The order of stability for the following cyclic olefins is peak? ol aay 0 aig Vv I (@I SS ia ® . & ' @ &@ @ er @ ee x x x x - HOW HOH H u 26. — The increasig order of basicity among the following compounds is (LON N(CHe HON NCH), (LON NICH): nen aces yw wy = ¥ HOD | OCs \ (a Y¥x>¥ (nn 31. The correct stability order of the following resonance str | uJ CRE) AEA rT 2 e ee ® e 2 8 H,C“N=N HjC—N=N H,C_NeN H,. © © wy w) (a) (D> (> (IV) >() (b) (1) > (I> I> (Ivy, (©) @)> (> an >avy @ att) > (D> (v)> | 32. Among the following compounds, the most acids is | (@ prritrophenol (b) p-hydroxybenzoic acid 0) (© o-hydroxybenzoie, acid (@) ptoluic acid » 33. Amongst the following, the most basic compound is » (a) benzylamine (b) aniline (c) acetanilide (d) p-nitroaniline | 34. What is the decreasing order of strength of the bases.? t RS OH”, NHj,H—C=C> and CH, — CH; (a) CH; —CH; > NH} >H—C=C~>08 = > CH —CH5 > NH5> Os (©) ORT > NAG > eeC scH, — cH; | (@) NH} >H—C=C7>0H->Ch,—CH | 35. Among the following compounds, the strongest acid is (@) HC=CH (b) Cyl © GH, (@ CH,On | 36. Among the following, the strongest base is (a) CgHNH, (6) pNO,CgH,NH, (C) m-NO,—C,H NH, (€) CgH,CH,NH, 37. The correct order of basicities of the following compounds is mt y e-G, (2)CH,CH,NH, (3) (CH) ,NH @)CH,CONH, NH) (a) 2>1>3>4 « (B) L>3>2>4 ©) 3>1>2>4 — @) 1>2>3>4 Hooc CH Be OF OC | _talsstatt, A, The product A will be CH OH . 28-B/7, Jia Sarai, Near IIT, Hauz Khas, New .B. Nagar, New Delhi - 110009 « South : e J11-41415514, 09136597244, Tall Free; 1800-200-4940.Heb.: warwichemacademy. ‘Delhi: 72, Mall Road, Delhi 110016 + Ph 2 C—O AAA A OAL 43. €.€ 6d bob b eb oda ‘The cmpound that gives precipitate on warming with aqueous AgNO, is Br " ir ue SS ® O © } © O @ QO N ‘The compound that is antiaromatic is “i B. 2 > ey ia ( oF wo Kym ) ev) [=o @I ul (mt @iv ‘The decreasing order of basicity of the following compound is Oe) gee o> oCY mF mw oO N N (a1>H>M>IV (b)IVeI> MoM = ©@Ml>l>I>1V @)IV>Ml>M>1 | «CATE ANSWER KEY a EXERCISE | o 1b 2b 3.a 4.b Sa i 8a a 10.4 iL.b 12.¢ i I5.¢ 16.b 17.b 18.6 19.6 a 2.4 23.¢ 24. 25.4 26.6 u 29.4 30.d 31d 32.4 33.4 Wi 36.4 37.d 38.0 39a 40. a Bic 4a 45.6 46.0 47.4 t 50.4 She 52.6 53.b 54.0 S7.¢ 58.8 59.4 60.B 6l.c 1 64.4 65.b 66.¢ oe 68.¢ I The na Bd 74,6 Ba t 7a 9.0 80.¢ Bla Ba ep I 85.a 86.4 87a 88.4 89.0 C 1 92.0 9316 4b gs \ my 99.4 100.6 10h.e 1020 » 106.d : 108.3 L I 113.b Te 2 Abie i 120.4 a 122.0 123. 124. tT EXERCISE-I bie | Lab abe 3.04 4ad S.acd 6.bd Tabed > Bac 9.abc 10.ac Lac 12. a,b,c 13.a,cd 14. be ° iS.ac I6abed 17.ab Babed IWabed Wabed 21. ab Co 2bd Badd ab — 25.be 26.abd 2abe 2B.abe 1 29.abd 30abe 3labed 32abe 3.abe 34.ab . EXERCISE II ~ 16 24 3.0112 4.4 5.12 6.3 17 x 8.9 9.4 10.6 1.6 12,90 13.65 14.38 15. (@)}8(0)6 16.12 17. (®cisis stronger acid as the Hof. Oss seers "CH, is operating not at 180°, so conjugation is not as destablized | Bigg EEE ica lade , 80 Conjugate is more stablized than Js m cis 4 18, (@)3>2>4>1()4>2>1>3>5 19. 2 23. 24. 25. VOUVUOFOSDOOO4OOHKC COVEY EYP TOTS No conjugation, + m effect of C-O is same in both, cH ° é[ One of the R.S. is having both ring aromatic, CH (1) Quasi (2) Quasi (3) Quasi (4) Quasi (5) It is antiaromatic but does not undergos dimerisedue to bulky t-Bu groups, (6) Quasi Eighteen electrons delocalised in porphyrin which satisfy the huckel’s rule @1<3<4<5<2 ()4cded<1 ()3<2<4<1 — (0)3<2<4<1 ()2<4<3<1 — ()4<1<3<2 (a)2<1<3 (b)3<1<2 ()3<1<2] ( a) Bens ey (1) 3*!*1P*is atatched to sp hybridised “C” stom so is most acitic (2) 24H atomis attatched to op hybridised “C” atom & 1* °C” atomattachod 10 sp? hybridised SC? atom. But anion formed is stabilised by resonance (b) 1882! Hr atomare present at 2” position to CoO group where 2 is directly attached to °N atom so is more Acidic which 31" is least. Acidi because te anion formed after protonation js not stabilised by resonance (o) 2&1" “H" atoms are ‘phenolic “H” atoms are more acidic than ketonic “e:” “H” atom. But {L gd “17° ig more acidic because - R of ~C~ group stabilised by resonance Re PING TSA ifs Mth hn Me @ (b) © @) ©) ‘ble ketone due to repulsion between two adjacent keto groups. (a) Highly unsta (b) Active tor / Acie" fom 0 his ve enolic ote el abs by soars Tm ‘molecular H-bonding) > (c) Enolic contents decreases with introduction of e- donor group which causes repulsion in enolic form. @ Due to ester group resosnace > (6) Lowest enolic content besanse 0-0 ismore stable than 2O-C< Bond ] acidic structure of active H decreases & C=C of enol undergoose cross Tc DLE WY Wines Mac New Cs | RN °o o 26, 21. + . II @ cH,-c-c ect,-¢-cr (double bond character) » 9-0 Pe oe In 1* compound due to mesomeric effect more double bond character between C & Nso that greater strength of bond. Wo 0 Hoo (iii) Ag in II compound due to ortho effect + m of ring is cut off.) dhl) prey POPPI L 4s ‘Out of plane d

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