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    WG Himanshu Pandey BOOKS CSE] ADVANCED PROBLEMS IN ror JEE (Main & Advanced) & All Other Engineering Entrance Examinations Pata s : Lucky Ce Ta FUSS a mee) ieemeiaal © Distribution Office G. R. BATHLA PUBLICATIONS PVT. LTD. {An 180 9001 = 2008 Certified Eatabichment) EDUCATIONAL PUBLISHERS & DISTRIBUTORS "Prakash Buldng”. Opa. Nayyar Palace, Lal Kurt, Moon UP) y Phones :o¥21) 2640308, 250304, 2660802, 2650700 9760235126 Enqury Dept) 7 (012s) 6482119, dereso4320 267 164072 (sles Dept) Oa) 6482010, ees2125, 2219516210 (OrdorSochng Deak) 3760327805, 9897275657 (Cuca Care Doo) me (0121) 2640056, «059720, 2664508, s03te12 ‘email: wenbetiaboots. com ‘weabsta :goania@ eat. com © Author . ISBN : 978-93-82314-46-2 < Q First Edition: 2010 Q Sixth Edition : 2014 © Price: % 452.80 © Printed a1 “Aryan Press, Mecrut (U.P) Ya part ofthis book may be reproduced in any form or by any means without the prior ‘written permission ofthe 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 lake any legal responsibilty forany misinterpretations or errors inadvertentlyoverlooked. PREFACE to the Sixth Edition === ‘An excellent response to previous edition, I fect 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-I 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 threc 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 leaned teachers. Suggestions for further improvement of the book will be gratefully acknowledged. T 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 ofthis book. : 1 would like to thanks Mr. Manoj Kumar Bathla and Mr. Vishvnath Bathla, Directors of G. R, Bathla Publications Pvt. (1d. for their effort in bringing out this dition: 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. SS SSS PREFACE to the First Edition “New Pattern Advanced Problems in Organic Chemistry for IT-JEE” has primarily been written with the aim of meeting the needs and interests-of student seeking 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 % The problems are based on basic concepts, preparations, properties, structures and usefulness of organic chemistry. ‘ 3 Due considerations have becn given to mechanism and stereochemical aspects of chemical reactions. X& Maximum problems in this book are designed by combining two or more ‘concepts. Answering them need thinking and deep knowledge. | 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. S.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 Put, 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, ereep in April, 2010 Himanshu Pandey CONTENTS Chapters Pages PAN a oko enue a § Exercise-1 : Only One Correct Answer Level-1 4 Level-2 9 Exercise-2 : More Than One Correct Answers 46 Exercise-3 : Linked Comprehension Type 56 Exercise-4 : Matrix Match Type 6 Exercise-S : Integer Answer Type Problems & Answers (eine § Exercise-t : Only One Correct Answer Level- 6 Level-2 B Level-3 86 § Exercise-2 : More Than One Correct Answers 110 § Exercise-3 : Linked Comprehension Type 119 § Exercise-4 : Matrix Match Type 123 4) Exercte-S ImtogerAnawer Type Problems us Answers 3. HYDROCARBONS (ALKANE, ALKENE AND ALKYNE) § Exercise-t : Only One Correct Answer Level-1 130 Level-2 137 § Bxcrcise-2 : More Than One Correct Answers 182 § Exercise-3 : Linked Comprehension Type 192 § Excrcise-4 : Matrix Match Type 202 § Exercise-S : Integer Answer Type Problems 206 2 Answers Es a Exercise-I : Only One Correct Answet Level-1 ” : 2 Level-2 - 218 § Exereise-2 : More Than One Correct Answers 252 4 § § > Urmanan wi) Exercise-3 : Linked Comprehension Type Exercise-4 : Matrix Match Type Exercise-5 : Integer Answer Type Problems Answers Exercise-I : 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 Exercise-5 : Integer Answer Type Problems Answers CRT aeons 4 Comme Ta eee ee Vereen Exercise-1 : Only One Correct Answer Level-| Level-2 Exercise-2 : More Than One Correct Answers Exercise-3 : Linked Comprehension Type Exercise-4 : Matrix Match Type Exereise-5 : Integer Answer Type Problems Answers Exercise-1 : Only One Correct Answer Level-| Level-2 Exercise-2 : More Than One Correct Answers Exercise-3 : Linked Comprehension Type Exercise-4 : Matrix Match Type Exercise-S : Integer Answer Type Problems Answers a 424 426-490} Umer Exercise-1 : Only One Correct Answer Level-| Level-2 Exercise-2 : More Than One Correct Answers Exercise-3 : Linked Comprehension Type Exereise-4 : Matrix Match Type Exercise-5 : Integer Answer Type Problems Answers (iy POTN) § Exercise-t : Only One Correct Answer Level-) Level-2 Level-3 Exercise-2 : More Than One Correct Answers Exercise-3 : Linked Comprehension Type Exercise-4 : Matrix Match Type Exercise-S.: Integer Answer Type Problems. Answers Ere 535 54s 553, 599 606 ois 617 a meses Cee § Exercise-1 : Only One Correct Answer Level-\ Level-2 Exercise-2 : More Than One Correct Answers Exercise-3 : Linked Comprehension Type Exercise-4 : Matrix Match Type Answers Qomen PRACTICAL ORGANIC CHEMISTRY EE) Bxercise-1 : Only One Correct Answer : Exercise-2 : More Than One Correct Answers § Exercise-3 : Linked Comprehension Type § Berchet Ma Math Type Answers Pane Section-1 Section-II Section-IIl Section-IV Hints & Solutions Ummmn “ 662 662 1. Which of the following belongs to +/ group 7 (a) —OH (b) —OCH,, (c) —COOH (@)—CH, 2. Which of the following is the strongest ~/. group ? 1 NCH), O—*NH, — ©—SCH). @—F | 3. Among the following compounds, the strongest acid is: (@HC=CH (®)CcHy OCH. (@)CH,OH 4. Carbocations may be stabilised by i (a) x - bonds only at allylic position 1 (b)m- bonds only at vinylic position | ()n- bonds at allylic and benzylic position also : (@) -I effect 1 '. In the anion HCOO™, the two carbon-oxygen bonds are found to be of equal length. What is the reason for it ? i (a) The C=O bond is weaker than the C—O bond. : (b) The anion HCOO™ has two resonating structures. (c) The electronic orbitals of carbon atom are hybridized. (qd) 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 ? esaiae fe Hetee CH;—CH,—CH—OMe «> CH,—CH,—CH=OMe : o m i @r on (©) Both have equal contribution (a) They are not resonance structures 7. The species CH, CHCHs is less stable than : (@)(CHy);C’—@)CH,CH CH, (@)CH,CH, (cnt Arrange in the oder of decreasing pK. | @)F—CH,CH,COOH (Q)c1—cH—cH,—COOH I a (8) F—CB,—COOH _(8)Br—-CH,—CH,—COOH | GRB Advanced Problems In Organic Chemistry for JEE | } | i , % 2, 14, Arrange the following in decreasing order of the pKa value, Correct answer is (@) Q>S>P>R (o) P>R>S>Q (©) R>Q>P>S (4) S>Q>P>R The strongest base is: H,N. NH “\4% @CH; eee ) [ cH, NH; CaM, NC (®CH,—NH—CH, ' Cols 10. Consider the following species : ° 2 e (you @a—8 oe, wn, ‘Arrange these species in their decreasing order of nucleophilicity. (@)C>D>B>A (0) B>A>C>D (QA>B>C>D ()C>A>B>D ‘Consider the following carbanions : gz 2 (1) H,Co- Ga, anon {O)- cH, 8 anO)- CH, Correct decreasing order of stability is (a) >> IV>1 (IV> I> 11> 1H On oH or NO; NO; 1 D a ‘Arrange the following phenols in increasing ortier of pKa value. @I 1V>1>1 @l>m>m>5v CH,=CHCH,—COOH —CH,CH,COOH w ay 0 Arrange the following acids in decreasing order of {H” } cone. @I>H>iM = )>M>1 = @M>I>m | @m>n>T General Organic Chemistry 3 (CH; =CHCH, NH, ,CH,CH,CH,NH,, CH=CCH NH, @i>i-m OU>I> ~Om>u>l ~ @Met<1 15. Arrange the following in increasing order of pKa value. ao Hi S Sg oO qa) (oy - @IIvIV>I>m>1 (I> I> ML>V>¥ @V=>iv>M>0>1 17. Arrange the following in increasing order of stability. Ome ap (@I >1> IV (b) I> >1>1V (@m > M1> IV (I> >> IV (c)1>1V> 11> 1 (@)IV>M>0>1 20, Which of the following molecules can act as a nucleophile and an electrophile ? (@)CH;NH, —— (b) CHCl (CHACN (@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; 22, Give the correct order of decreasing basicity of the following compounds. CyHSNH,, © (@I>m>m>1V (©Iv>1> i> I (CsHs)2NH — (CoHs)3N — CgHy) NHz ay am w @)IV>m>1>T @ M>1>1>1V 23. The correct order of stability of the following carbocations is (@)CH,CH, CH, >CH. CH—CH, 3CH, =CHCHCH, > CH, =CHC(CH, 2 () CH=CH, > CH,CH,CH, > CH; = CHE(CH,), > CH,=CHCHCH, “HC(CH,)>CHy =CHCHCH, >CH, =CHCH, >CH,CH,CH,, it uce, >cn, ~-cHéen,),>c10,—2n, > CH, =CHCH, 24, The order of deereasing stability ofthe following cations is ea Gaeai accuser aencoal o a am @>u>t @oMeM |mm — @I>m>u 25, Whatis the decreasing order of strength ofthe bases ? @ow ay NH (iy H—Cec> (AV) CH CH (@)IV>H> I> 1 (ui Ivanar (I> U>M> IV. (@M>M>1>1V 26. ‘The decreasing order of nucleophilicity among the nucleophiles is CH, 6-0" (ay cN~ (@)1>1>m>1V = (M>m>1>IV 27. Different hydrogen in (I) CH,” oO I ()IV>m> > 1 (@M>H>1>1V B o¢.-D OE F (CH\CH=CH—CH;—CH,—CH(CH;)2 General Organic Chemistry 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>E (a) A> B> C>D>E>F 28, Consider the following : : O=C—NH, 9 CH,CH;NH;, CHCNH,, 0 om a Correct order of their basic strength is : @ichl>m (~@M1> n> @U>I> > IV Consider ON ALAN 9° ° eerie tT ‘The correct order of their acidity is: (a> I> m> IV (@Iv>M>nal ‘The correct order of decreasing basicity of the above compound (a)1>U>>IV (ul>WV>U>1 Select the correct order of basici (@)CH,CH; > CH, (b)CH,CH; > HC= (©) CH,CHG > OH” > Hi (@)OH > HCC” >CH, S a Gini 0 @m I> 1V>11 @i>m>1>Vv (ON Zr0_-_-NO, ° ° mm SS, No oO (n> >1>1V (@) none of these a coo) nt ay) NE Ne ()U>T> vem @m>1> sv CH > HC==C~ > OH General Organie Chemistry Zz 37. The acidity of the protons HT in the following is = iL { ()CH,CH,CCH, (11) CH,CH,OCCH, Yd (Ill) CH,CH,OCCH, COCHCH; (@I>U>i = (ISM | @M>I> MM @Ml> > 38, Which comparison is not correct as indicated ? (a) C\-0n >CH,OH (acidic nature) wo Sw, SCH Nt; (sie nane) < scat Sit, (abit) @ O-bow-cdon {acidic nature) 39. How many x electrons are there in the following species ? QO fa)2 (o)4 6 @8, 40. Which of the following is not correct ? ‘ (2) A sigma bond is weaker than % bond. (0) A sigma bond is stronger than % bond. (©) A double bond is stronger than a single bond. (@) A double bond is shorter than a single bond 41, The length of the cazbon-carbon single bond of the compounds (I) CH, =CH—C™=CH (I) CH==C-—C=CH (HI) CH, —CH=CH, (V)CH, =CH—CH=CH, is expected to decrease in the order @ > 1>1>1V (by 1> > >I Poms (@i>IV>1> ML . Which of the following involves no displacement or shifting of electrons ? eG Zeeman effet (b) Inductive effect (©) Resonance (@) Electfomeric effect 43, Which ofthe following exhibit eletromeric effect? a) Alkanes (b) Aldehydes (©) Alkyl halides (@) Alky! amines GRB Advanced Problems in Organic Chemistry for JE 44. Point out the incorrect statement about resonance. (a) Resonance structure should have equal energy. (b) Inresonance structures, the constituent atom should be in the same position. (©) In resonance structure there should be the same number of electron pairs. (4) Resonance structures should differ only in the location of electrons around ‘the constituent atoms, 45, Resonating structures of molecules have {) identical bonding (b) different bonding (©) identical arrangement of atoms and nearly same energies (4) the different number of paired and unpaired electrons 46. Shifting of electron ofa multiple bond under the influence of 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 aw on (coos (Iv) -Cm=CH @)Il 1V>m>1 @M>t> won (@In>I>m General Organic Chemistry 8 49. Resonance energy of these compounds will be in the order as : oS oS MANS . I ° i H (a) MI>I>n (b)1> 0 > (> M>T @U>1>m 11. Which of the indicated H in the following is most acidic? ¥ i je HO Hoy ® if WHO ” @x wy Oz os 2. In which of the following compounds is hydroxylic proton the most acidic? @ I @ @ DN, OAAN ONG An F F 3. Which of the following pairs does not represent the resonance contributors of the same species? e ° iat, (@) CH=CH” = and CHy—CH ® cH cH oe 7 © Cth Cit, and CH, Che oth © | SoH—CH and [- "CH=CH, cH” Ch, oe 27° ed @ CNC and CHIN 4. Which of the following is not a planar molecule? (a) HC=C=CH (b) H,C=C=C=CH, 5 Qe cs2, (@) NC—HC=CH—CN . Which ofthe following pairs does not represent resonance structures? (@) CH coh Sandc CaN ° ) ch and ahd, | 10 GAB Advanced Problems In Organic Chemistry for JEE @ oO OH @ coo and cat ‘NH; ‘NH 6. In which of the following pairs is the structure on the right major resonance contributor? ; e ° 6 4 (@) cHy—c& Hef 5 7. In which of the following pairs of resonance contributors is the structure on the right a important contributor? eo ° — HC 0% eo ee () CH,—N=N <> CH, = @ e (©) CH, —CH—OH <> CH,—CH=OH (@) All of the above 8. Examine the following resonating structures of formic acid and arrange them in decreasing order of stability g 0, ®0 08 le | | H—C—OH <> H—C=0—H <> H—C—OH > H—C—on ee “ o ap ay i) (@) W>1>mI>1V (b) [> 11> I> 1V (c) >> 1V>1 @ WV>M>i>0 9. Which of the following compounds will not show resonance? *CH @ (© cH,

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