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