Hig} = Himanshu Pandey BOOKS CEE] ADVANCED PROBLEMS IN __ For JEE (Main & Advanced) & All Other Engineering Entrance Examinations Check ; Lucky *, id ey wi eS Pair reat .4 a ay aa wheD Distribution Office : G. R. BATHLA PUBLICATIONS PVT. LTD. (An 180 9001 : 2008 Certified Establishment) ~ EDUCATIONAL PUBLISHERS & DISTRIBUTORS. “Prakash Building’, Opp. Nayyar Palace, Lal Kur, Meerut (U.P) . Phones : (0121) 2640303, 2640304, 2660802, 2660709 + 9760235126 (Enquiry Dept). . . (0121) 6482119, 9219404920) 9267164022 (Sates Dept) + (0121) 6452010, 6452126, 9219515310 (Order-Booking Dep.) + 8760327805, 9897275667 (Customer Care Dept) Fax: (0121) 2649956, 4059720, 2664539, 4031412 ‘e-mail: wor bathlabooks.com ‘website ¢ grbathla@roditimall.com SS © Author . ISBN : 978-93-82314-46-2 “ Q First Edition : 2010 O Sixth Edition : 2014 Q Price: % 452.80 0) Printed at: Aryan Press, Meerut (U.P) © No part of this book may be reproduced in any form or by any means without the prior written permission of the author and the publisher. * The author and the publisher have made every effort to provide authentic, accurate and ‘up-to-date information in this book. However, they do not take any legal responsibility for any misinterpretations or errors inadvertently overlooked. .PREFACE to the Sixth Edition ‘An excellent response to previous edition, I fee! great pleasure in presenting fully revised edition of the book “GRB Advanced Problems in Organic Chemistry for JEE” according to latest pattern of examination. This book deals with objective problems of each chapter which include Single Choice, Multiple Choice, Matching Type, Comprehension Type and Integer Type Problems. Exercise-! in every chapter contains two levels, Level-I is for JEE-Main and Level-2 is for JEE-Advanced. “This book is highly desirable that students, particularly those who: work very much on their own, should have a mean of achieving confidence in organic chemistry”. The study of Organic Chemistry requires at least three processes : Learning, Understanding and Application. A very good way of achieving it, is through solving the problems. : 1 do hope that the new revised edition of the book will be more useful to the students and leamed teachers. Suggestions for further improvement of the book will be gratefully acknowledged. I wish to acknowledge my indebtedness to all the faculties across the india for their enthusiastic support and their useful suggestions given from time to time for improvement of this book, . : J would like to thanks Mr, Manoj Kumar Bathla and Mr. Vishvnath Bathla, Directors of G. R. Bathla Publications Pvt. Ltd. for their effort in bringing out this February, 2014 Himanshu Pandey Note : Students and honourable teachers may feel free to give valuable suggestions on the mail suggestionsgrb@gmail.com to improve the quality of book. nePREFACE to the First Edition “New Pattern Advanced Problems in Organic Chemistry for I'T-JEE” has primarily been written with the aim of meeting the needs and. interests-of student secking admission to professional courses especially in engineering and medical, The present book on organic chemistry is designed especially in accordance with the new examination pattem and syllabus of IIT-JEE. The main objective of preparing this book is to keep pace with the changing trends of entrance examinations. To make the students more familiar with trends and tricks, how to solve problems, the present problems book has been prepared. The other salient features of the problems book are summarized below. . a 3 The problems are based on basic concepts, Preparations, properties, structures and usefulness of organic chemistry. : 3 Due considerations have been given to mechanism and stereochemical aspects of chemical reactions. 3& Maximum problems in this book are designed by combining two or more concepts, Answering them need thinking and deep knowledge. : I wish to acknowledge my indebtedness to Mr. Amresh Sharma, Mr. Amit Mishra and Mr, Vivek Pathak for their enthusiastic support. 1 acknowledge the blessings and support of my mother Smt, Kalindee Pandey, father Dr. 8.N. Pandey, uncle Shri Sudhakar Pandey, brother Sudhanshu, Saurabh and my wife Jaya They supported me all the time during the preparation of book. I would like to thank Shri Manoj Kumar Bathla and Shri Vishvnath Bathla, Directors, G. R. Bathla Publications Pvt. Ltd., for their effort in bringing out the book. The author will be grateful to teachers and students, if they be kind enough to offer criticism and suggestions for its improvements and to point out the inevitable errors which, inspite of all efforts, creep in. April, 2010 Himanshu PandeySie Chapters Pages GENERAL ORGANIC CHEMISTRY bss § Exereise-] : Only One Correct Answe Level-1 : . 1 Level-2 : : 9 § Exercise-2 : More Than One Correct Answers’ oo 46 § Exercise-3 : Linked Comprehension Type . 56 § Exercise-4 : Matrix Match Type - 62 § Exercise-S : Integer Answer Type Problems 65 > Answers 67 ISOMERISM ers, § _Exercise-1 : Only One Correct Answer : Level-1 69 Level-2 . 8 Level-3 . . 86 § Exercise-2 : More Than One Correct Answers 110 § Exercise-3 : Linked Comprehension Type . 119 § Exercise-4 : Matrix Match Type 123 § Exercise-5 : Integer Answer Type Problems 128 Answers 128 2 EM Nays ecer cin ek Cesta ie ac Ne nL) ray § Exercise-1 : Only One Correct Answer . . Level-| ; : 130 Level-2 137 § Exercise-2 : More Than One Correct Answers 182 § Exercise-3 : Linked Comprehension Type 192 § Exercise-4 : Matrix Match Type 202 § Exercise-5 : Integer Answer Type Problems 206 2 Answers mors 209 Ce a) 211-278} § Exercise-1 : Only One Correct Answet > : Level-1 7 : 21 Level-2 nee : : 218 § Exercise-2 : More Than One Correct Answers 252(vi) § Exercise-3 : Linked Comprehension Type 263 § Exercise-4 : Matrix Match Type 270 § Exercise-5 : Integer Answer Type Problems 214 3 Answers . 277 ERE at eet nai) ee § Exercise-1 : Only One Correct Answer Level-1 219 Level-2 : 289 § Exercise-2 : More Than One Correct Answers 318 § Exercisc-3 : Linked Comprehension Type : 329 § Exercise-4 : Matrix Match Type : 337 § Exercise-5 : Integer Answer Type Problems . 340 3. Answers : 343 AIT moo nels Eee § Exercise-1 : Only One Correct Answer Level-1 345 Level-2 354 § Exercise-2 : More Than One Correct Answers 394 § _Exercise-3 : Linked Comprehension Type 404 § Exercise-4 : Matrix Match Type 417 § Exercise-5 : Integer Answer Type Problems : au > Answers 424 7. CARBOXYLIC ACIDS AND ITS DERIVATIVES 426-490) § Exercise-1 : Only One Correct Answer Level-I 426 Level-2 433 § Exercise-2 : More Than One Correct Answers 465 § Exercise-3 : Linked Comprehension Type 476 § Exercise-4 : Matrix Match Type . 484 § Exercise-S : Integer Answer Type Problems 486 2 Answers . . 489 8. AMINES ere § Exercise-I : Only One Correct Answer Level-1 401 Level-2 497 § Exercise-2 : More Than One Correct Answers 518 § Excrcise-3 : Linked Comprehension Type $24 § Exercise-4 : Matrix Match Type 530 § Exercise-5 : Integer Answer Type Problems 532 3 Answers 534(vii. Prete h ee aceneau enous § Exercise-1 : Only One Correct Answer Level-1 Level-2 Level-3 Exercisc-2 : More Than One Correct Answers Exercise-3 : Linked Comprehension Type Exercise-4 : Matrix Match Type Exercise-5:: Integer Answer Type Problems Answers Comma 10. BIOMOLECULES § Exercise-1 : Only One Correct Answer Level-1 Level-2 § Exercise-2 : More Than One Correct Answers § Exercise-3 : Linked Comprehension Type § Exercise-4 : Matrix Match Type 2 Answers 11. PRACTICAL ORGANIC CHEMISTRY § Exercise-1 : Only One Correct Answer § Exercise-2 : More Than One Correct Answers Exercise-3.: Linked Comprehension Type § Exercise-4 : Matrix Match Type Answers: > 12. NOMEN eit Section-I Section-IT Section-IIL Section-IV Hints & Solutions Bowmmm KER ye 535 545 553. 599 606 615, 617 621 xe ys 623 626, 634 637 640 64: TRE) 12 643 | 647 650 651 654 TAY 655 660 662 662 663at[ auave< 1. Which of the following belongs to +/ group ? (a) —OH ()—OCH, © ()—COOH = @) —CH, 2. Which of the following is the strongest ~ group ? ' (@)—N*(CHy)3 ()—*NH; —— (©)—"*SCHs)., @—F | 3. Among the following compounds, the strongest acid is : (@HC=CH —O)CgHe ()CrHg (®CH,OH 4. Carbocations may be stabilised by : | (@)m- bonds only at allylic position : (b) n- bonds only at vinylic position (©) x- bonds at allylic and benzylic position also ‘ @-Leffect | "5. In the anion HCOO”, the two carbon-oxygen bonds are found to be of equal , length. What is the reason for it ? i | @) The C=O bond is weaker than the C—O bond. : i (b) The anion HCOO™ has two resonating structures. | (©) The electronic orbitals of carbon atom are hybridized. | (d) The anion is obtained by removel of proton from the acid molecule. | 6. Which of the following resonance structures is the major contributor to the {resonance hybrid ? aa 1 i CH,;—CH,—CH—@Me = CH,;—CH,—CH=OMe ; ” ay { @l ) I i | {Both have equal contribution _(@) They are not resonance structures | 1 | 7. The species CH, CHCH, is less stable than : : + * i (a) (CH3)3C* (b)CH3CHy CH, = (c)CH;CH2 (d) CHS i «8 Amange inthe order of decreasing pK. | | @)F—CH,CH,COOH (Q)cl—GH —CH,-~ COOH ' a t _@)F—CH,— COOH __(S) BCH, CH," COOHt 2 GRB Advanced Problems In Organic Chemistry for JEE Correct answer is : - 7 (a2) O>S>P>R (bl) P>R>S>Q (c) R>O>P>S (d) S>Q>P>R 9. The strongest base is : HN NH *\4 (@)CH, rs ) € CH; NH, (CoH Nols (CH,—NU—CH, Cols 10. Consider the following species : : 8 2 @ | (AyOH (a)cH,—8 = (CE, (D) NH, Arrange these species in their decreasing order of nucleophilicity. ! (a)C>D>B>A (b)B>4>C>D ()A>B>C>D (@C>A>B>D 11. Consider the following carbanions : 2 g @ #,00-{O)— cH, ano.n—(O)- CH, g . 2 an) cH, avy) 5e-{O)- CH, ! Correct decreasing order of stability is : @)>M>1V>1 (ey > 1V>1>0 ()IV>I>1> I (@1>>m>IV i OH OH OH NO, 12. | NO} i NO; ‘ I n a : Arrange the following phenols in increasing order of pKa, value. @IH>M =) M>M>1 = @M>I>@)IN> HoT |. Arrange the following in decreasing order of the pKa value. ee ee Sa ee ceGeneral Organic Chemistry 3 CH, ==CHCH,NH,CH;CH,CH,NH,, CH==CCH,NH; @I>t>l ‘@)N>I>m = © W>u>t ~ @uuIVIV>I> >I ()1> > HI>IV>V (@V>Iv>Ml>n>1 17. Arrange the following in increasing order of stability. Oo an aD @i<0I >1>IV {b) I> 1 >1>1V ()MlU>H1>IV () I> 1 >T>I1V (}1>1V> > (@IV>mM> > 20. Which of the following molecules can act as a nucleophile and an electrophile ? (2) CH;NH, (b) CHCl ()CHCN (@)CH,OH“4 GRB Advanced Problems in Organic Chemistry for JEE 21. Which of the following molecules has the shortest carbon-carbon single bond length ? (@) CH, =CH—C—CH (b)CH, (©) CH, =CH—CH=0 (CH, 22. Give the correct order of decreasing basicity of the following compounds. CoHsNH, (CoHs)2NH = (CsHs)3N 9 CgHiNHz oO ay ay, av) (a)I>M>m>tv (b)IV>IN>>T ()IV>I>I>I0 (d) > >1>1V 23. The correct order of stability of the following carbocations is : (a) CH,CH, CH, >CH, =CH—CH, 3CH, =CHCHCH, > + CH, =CHCICH,), (0) CH,==CHCH, > CH,CH,CH, >CH, =CHC(CH;), >CHiy=CHEHCH (och, =catcH, ).> CH, =CHCHCH, >cH, =CHCH, >oH,CH,CH, (@) CH, =CH—CHCH, > CH, =CHG(CH,),> CH,CH,— b> =CHCH, 24. The order of decreasing stability of the following cations is : CH,CHCH,, CH,CHOCH,, CH,CHCOCH, Ww . aby ap. (a) I> U>1 (b) I> > OE () I>1> 01 @I>m>u 25. What is the decreasing order of strength of the bases ? (OH- (I) NHZ (my)H—C=c- (IV) CH, CH; @Iv>I>m>1 - (b) I> IV>>T ()1>1>M>1V (@)U> H>1> IV 26. The decreasing order of nucleophilicity among the nucleophiles is : CH; aan (i) CH," vo t (uy en" ay) wef S20” ° (a)I>T>>IV . (b) IV >>> .. ©U>m>1>1v (@M>1>1>1V 27. Different hydrogen in Booc. Dp UE OF cer CH—CH,—CH,—CH(CH,), cfGeneral Organic Chemistry 5 are represented by alphabets. Arrange them in decreasing order of reactivity towards radical substitution. (@)C>A>E>D>F>B (b)F>B>A>C>D>E ()B>C>A>F>D>B (@) A>B>C>D>E>F 28, Consider the following: - / O=C—NH, g CH,CH,NH,, CH CNH, o a (mt) Correct order of their basic strength is : @I1>M @WI> > 0 (@U>1>M>1V Consider o es The correct order of their acidity is : @U>I>m>v @IV>M>n>1 om ay NO;—{O)—N @) I 1>1V>11 (@ I> > I> Iv (I) NN ANN 9 ww) sh A (b) >I >1>1V (d) none of these (ay a0) NH) ayy NE N ‘The correct order of decreasing basicity of the above compounds is : (a) I> I> > IV (@)MI>IV>0>1 . Select the correct order of basicity. () > 1> I1V>0 (@U> I> IV (a) CHCH3 >CH,=CH™ > HC=C” >OH™ (b) CH,CH3 > HC=C™ >CH, =CH™ >OH™ (0) CH,CH; > OH > HC= (@) OH" > C=C” > CH, = ~ > CH, =CH™ CH >CH,CH3 eg- General Organic Chemistry 37, The acidity of the protons H* in the following is : Oo ll th (0) CH,CH, CCH, (11) CH,CH,OCCH, q 1 (If) CH,CH,OCCH, COCH,CH; (a)1>U> 1 (b)1>l> it (o) I>1> (d) 11>1>0 38. Which comparison is not correct as indicated ? “(a) € \-on >CH,OH (acidic nature) , o€ Swi, >CH NH, (basic nature). e ® © ( \-&, >CH, CH, (stability) ° ° @ € Son > cu,lou (acidic nature) 39, How many rr electrons are there in the following species ? YX 2 (a2 4, (0) 6 8, 40. Which of the following is not correct ? “ (a) A sigma bond is weaker than m bond. (b) A sigma bond is stronger than % bond. (c) A double bond is stronger than a single bond. (@ A double bond is shorter than a single bond. 41. ‘The length of the carbon-carbon single bond of the compounds (i) CH, =CH—C=CH (i) CH=C-—C=CH (I) CH; —CH=CH, (IV) CH, =CH— CH=CH, is expected to decrease in the order : (@) HI> 1>1>1V (b) I> I> > 1V (co) I> Iv >1>T (d)1>IV>1>1n 42. Which of the following involves no displacement or shifting of electrons ? (2) Zeeman effect .~ (b) Inductive effect (c) Resonance (@ Electromeric effect 43. Which of the following exhibit electromeric effect ? (a) Alkanes : : (b) Aldehydes (©) Alky! halides @ Alkyl amines8 . GRB Advanced Problems in Organic Chemistry for JEE . 44. Point out the incorrect statement about resonance. (a) Resonance structure should have equal energy. (b) In resonance structures, the constituent atom should be in the same position. (c) In resonance structure there should be the same number of electron pairs. (a) Resonance structures should differ only in the location of electrons around the constituent atoms, , 45. Resonating structures of molecules have (a) identical bonding () different bonding (©) identical arrangement of atoms and nearly same energies (d) the different number of paired and unpaired electrons 46. Shifting of electron of multiple bond under the influence of a reagent is called: (a) Leffect (b) M-effect (© E-effect (d) T-effect : 47. Give the correct order of increasing acidity of the following compounds. © OH a OH ay (coon avy) C=CH @lu1V>1>1 (b) I> 1>IV>1 (I< UU>1> IGeneral Organic Chemistry” ** 9 49. Resonance energy of these compounds will be in the order as : ofS mS mMAN~ ~ N 0 H a | H @M>I>n >> (]U>mM>I @u>1>m 1, Which of the indicated H in the following is most acidic? H | @ HN N H ” n” HHO ” . (@) X &) ¥ @Z @p 2. In which of the following compounds is hydroxylic proton the most acidic? F @ LA, OAA, ow a) we 3. Which of the following pairs does not represent the resonance contibutors of the same species? o t | (=) CHy—CH” and cy 7 @ oN (b) CH, CHa and CH),—CH, on © i | >ot—Gis and t / AC 0 pp ay! a @ CH NC, and HNC 4. Which of the following is not a planar molecule? (a) H,C=C=CH, (b) H,C=C=C=CH, (©) HyC=C=0 (@) NC—HC=CH—CN . Which ofthe following pairs does not represent resonance structures? @ @ CH ComN—O and Hy C= NO . ee of (b) cian and CH>—NC Ge Py10 GRB Advanced Problems in Organic Chemistry for JEE on @ cat.—Ko e Sgn CN 6. In which of the following pairs is the structure on the right major resonance contributor? : : e 3 oO a Z (@) CH;—C <> CHy—C aan b—CK 9 - ° {b) CH, =CH—Cl) <— CH,—CH= op-o pes Ci CH go © nm’? — Jo 9 Tn whieh of the following pairs of resonance contributors is the structure on the right a important contributor? o eo se @ ° (») CH,—N=N <> CH,=N=N o 6 (c) CH;—-CH—-OH <> CH;—CH=OH (d) All of the above 8. Examine the following resonating structures of formic acid and arrange them in decreasing order of stability : op ety cw la cul H—C—OH ‘H—C=0—H H—C—OH <> H—C—OH a ay i) aw) (a) W>1>Ul>Iv (b) [> 1>I1>Iv (c) I> 1>IVet (d@) IV>MI>1>1 9. Which of the following compounds will not show resonance? b : °CH: @) CO (b) CH==CH—CH=CH—CH,General Organic Chemistry 1" i HN—H © @ OO 10. Which of the following compounds will exhibit d-orbital resonance? 7 20H Cz @ Os ) o © Co @ O 11. Which of the following represents resonating structure of ? ~~ QO C4? “© Ce <(d) All of these 12. Which of the following is not a permissible resonating form? e 8 e ° @ CH —¥—0 (b) CH, =K-0 CH; cH; ® ° (c) CH, “y=0 (d) CH —N=0 _CH, CH; 13. Less contributing stuctre of nitroethene is : o e 8 (a) CH cr 8G (b) CHC NCs : 3 . 9 @ ‘e409 . © Giy-Gt-KK @ Cc ae . 0 14. Which will be the least stable resonating Structure? oO + (@) CH, =CH—CH-CH—NH, (6) CH,—CH—cH CHNA, e eo (©) CH,—CH=CH-CH=NH, (@) CH =CH—CH—CH=NH,12 GRB Advanced Problems in Organic Chemistry for JEE 15. Which will be the least stable resonating structure? ae) 0 9 KS w (nt ° © Oye @ O86 16. Which of the following pairs of structures is not a pair of resonating structures? (a) H—C=NHand H_C=N—H (b) CH; —-CH=CH—CH, and CH,CH,CH—=CH, © CHy—P=CH—F— CH, and cH, pC —e—c, s ° @ olde % 17. Which of the following pairs of structures does not_represent resonating structures? oO OH A ll | { (a) CH; —C—CH, and CH, —C=CH, oOvoml 4 ®0—H OH (c) CH; —C—CH, and CH; —C—CH, ° 0 0 ° e (@) CH, =C=0 and CH, C=O 18. The most stable resonating structure of p-nitrosobenzene is : { t t { Ne Ne N® en ® () © © 0 @ () : N e Ng ° \ és oN 3 o ‘8General Organic Chemistry 13 19. Which of the following molecules has longest C=C strength? (a) CH, =C=CH) (b) CH; —CH=CH, CH; | © CH, —E—CH= CH (@) CH; —C=CH, | CH; CH; 20. The decreasing order of bond length of C=C in the following compounds is : OO OO Tl O) neisaveim ) tit> >> (©) > >1> 0 : @ IV>t> i> 1 21. In which of the following molecules all the effects namely inductive, mesomeric and hyperconjugation operate? oC a _ ©) (ls ° © Cpe of . CHs : 22. There. are three canonical structures of naphthalene. Examine them and find correct Statement among the following : . 1 1 . 1 2 2 2 <> _ 4 4 4 {a) All C—€ bonds are of same length (b) C,—C, bond is shorter than C;—Cy bond (c) Cj —C, bond is larger than C,—C bond (d) None of the above ‘NH NH} “0 S J ave it IV14 GRB Advanced Problems in Organic Chemistry for JEE Among these compounds the correct order of C—N bond length is : (a) IV>1>i> Tl - (b) M>I>T>1V (c) I> 11>1>1V @ ML>1>1V>0 24. C, —C, bond is shortest in : 2 2 : C=CH | CH=CH, ® ©) Cy 2 2 | CHr—CH, | C=sCH © @ 25. Among the following three canonical structures what would be their relative contribution in hybrid? Ci; =CH—CH—CH—CH=CH, I =CH—CH—CH=CH—CH) re eo e CH, —CH=CH—CH=CH—CH, m @Pn>M @)M>m>I @I>M>n @m>1>-n HOH il 26. CH" CH “CHB (CH, —H C\—H, C)—H, C,H and C, —H the homolytic bond dissociation energy is in the order : (a) C,—H>C,;—H>C,—H>C,—~H (b) C; -H>C,—~H>C,—H>C,—H (¢) C, —H>C,;—H>C, —H>C,—H (@) C, -H>C,—H> C,;—H> C,H 7. Which of the following bas longest C—O bond? “oY cy oct « o 28. In which of the following molecules electron density in ring is smaxinom? NO, 6 wl 96 8 3 ® H,C—N=N -H,C—-Ne=N -H,C_N=N a amy ayyGeneral Organic Chemistry 15 (a) I> > IV > (b) I> W>M>IV (©) > I> l>Iv @ M>1>Iv>0 30. What is correct increasing order of bond lengths of bond indicated as I, 1, III and TV in following compounds? 1 Wow : WY oll (a) << I2>3 (b) 1>3>2 ©) 3>2>1 (@2>3>1 33. The C—CI bond length is shortest in : (a) CH, =CH—Cl; (b) CH;—Ch (c) C6Hs—CH,—Cl (@) CH,=CH—CH,—Cl 34. Which of the following pairs of structure are resonance structure? CH;—O? CHy—O® a | es and Il yc CHs—C=NC H3C—C-NC Nou . ‘CH e 0 @ ,OH . @& (Calig,CU-NE and (Catt, C=NC 8 3 (a) Land 4 (b) 2and3 (©) Land 2 @ All of these16 GRB Advanced Problems in Organic Chemistry for JEE | 35. Which of the following is pair of resonance structure? @ @) iol () AC and oS oO OH ©, jo] . (@) AA oe AR 36. The most stable diene is : —s a @~wVv oA ovcnsdar~~~ 37. Which of the following cation would have greatest stability? CH we @ @ o ® N—CH, (c) CH; O—CH, (d) 3F CH, cH,” o a 38. Which of the following is not valid resonance structure of polyene? a”AY oY © AY @ NY 6 4 39, Most contributing structure in nitrocthene is ; o (a) CHs—S—CE) (b) e 0 e 2 eS (@) CH,=CH-NZ 5 () ben SZ ‘6 3 . e 20 * « 0 <3 @ CHy—CH=N 9 40. The most stable resonating structure of CH, —O—CH=CH is: @ 8 (b) CH; -O=CH—CH, e ) (@) CH,—O—CH—CH, & "OD OO . ‘aGeneral Organic Chemistry 17 42. The correct stability order of following species is : ow / i ey A! Om mM ®. (a) X>¥>W>Z(b) ¥>X>W>Z() X>W>Z>Y ® ) z>x>y>W 43. Choose the correct statement : (a) [effect operate in both o and x bonds () effect create net charge in molecule (©) [effect transfer electron from one carbon to another (d) J effect create partial charges and it is distance dependent 44, Which carbocation is most stabilised among following? aC ID #OD . Which one of the following is most stable? $284 OH 46. ‘Which of the following cations is most stable? ma oh, “OQ. Oe, : 3 Hy s 17. Which of the following cations is most stable? CH; CH; . @ Cy / CH, . ) CH” c/o i 8 3 CHs an os © Cv / CH: . @ Cc Ho“BY Ob wc/8 on 48. Which of the following carbanions is most'stable? 8 e: (a) CH;—CH, (b) CH;=CH—CH, ° “NH Il Il (©) CH;—C=CH, | @ CH;—C—CH,18 . * GRB Advanced Problems in Organic Chemistry for JEE 49. In which ofthe following 2nd anion is more stable than frst? * (@) 0,N—CH, and F—CH, (6) Cy and CCl, ° Ile 8 () F,C—CH, and cc—CH, (d) CH;—-C—CH, and H,N—CH, 50. Arrange the following carbanions in decreasing order of stability : 2 e ° e CH,=CH © Ph—CH, CH, =CH—CH, ) @) ® © (@) P>Q>R>S (b+) S>Q>P>R © S>Q>R>P @) Q>S>R>P 51. Arrange the following cations in decreasing order of stability = ° : . e eo oe CH,=CH—CH, Ph—CH, CH,;—CH, ® ~ @) @) (S) (a) P>R>Q>S (bl) R>P>S>Q (c) G>R>P>S (d) P>Q>S>R 52, Among the following which is most stabilised cation ? . ; INE, INH By ony oN, «T 6 53. Which of the following anions is most stabilised? @ jl » ff Aa, AA 900 . © Jel . (@) All have same stability os 54. Arrange the following anions in decreasing order of stability : ° ° ° ° Atl so I le Il H—C—CH—C—H CH; —C—CH—C—H e) @) ° ° lo Il os CH,—-C—CH—C—0—CH, @®) (@) R>Q>P (b) O>R>P (©) P>R>Q (@) P>Q>RGeneral Organic Chemistry : 19 55. Which of the following is most stabilised by ech ‘ os CHCH; wa Hy0-b-CH, 6 Se Ged =. The decreasing order of stability of following cations is (Question No. 56-60). °CH, Ha Hy ‘Hy 56. : : OH NH CH; fol (R) S (@) P>Q>R>S (bt) Q>S>R>P (©) Q>P>S>R @ Q>P>R>S “O a 21, o :0H * hat cw, “ (Q) ' (@ P>R>Qrs (o>Rss>P (c) R>S>Q>P (9 Ponere ®CH, : ord 56 ” @ . : (@—) Q>R>P>S © ay S>Onn>P (©) S>R>P>Q Ores CH: . gh, (e) P>O>R>S o P>S>Q>R ©) PoR>0>8 (d) S>R>Q>P20 GRB Advanced Problems in Organic Chemistry for JEE H, = °CH, °CH) 60. 7 CH; CH,CH; Cs HC—F—ely ba, bu, 2) @ ®) o (®) S>R>Q>P (b) P>O>R>S (0) Q>R>S>P (d) R>S>P>O => The decreasing order of stability of following anions is (Question No. 61-65). $6 Ss : @®) () O>R>5>P @ArgsPos (s>PoRr>0 (d) P>Q>R>S ease ( P>0>R>s DO>aapss. e) P>R>Q>8 (d) S>R>Q>P oO Bo: or ich gb z @) P>O>R>s @ S>R>Q>P "O>ssR>P (@) Q>R>S>PGeneral Organic Chemistry . 21 fe : ecH, Hy CHACHs Hs me—F—CHs ba, CH; P,Q? ®) © (a) R>S>Q>P (bl) P>S>R>O (0) Q>P>S>R (d) S>R>Q>P 66, The most unlikely representation of resonance structure of rnitrophenoxide i is: 8. 8 Re ah RP aap Dog Df 67. Which wa be least stable resonating site? (a) cH cE Ct |5 (b) ch, —¢ H—CH=CH—OCHs (© tf, —CH=CHCH—O—CH, (4) CH =cH—Cu—cH-0—cH, 68. Which of the following acids has lowest value of dissociation constant? @ CHy—CH—COOH by GHa—CHl,—COOH F . *F (c) CH, CH, COOH @ CHy—FH—COOH Br . Br 69. Arrange t the following acids in decreasing order of acidity : ° 1 i Woon H—C—OH CH, —C—OH > Ow . w) @® @) X>Z>¥ ) X>¥>Z () Z>X>¥ (@) Z>Y¥>X 10. Which of the following acids has towest pK, value? o . . oO ool I @ Gia C—OH ~ (b) oH, — CH, --C—OH , . | + .NO2 : NO,