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ceNII Bala M.S. Chouhan WE REL ORGANIC CHEMISTRY _ JEE o gogaao0 SHR! BAN ee aTHGUTORSI FEDUGATIONAL PUGLISHERS & DISTRIBUTORS) | 6, Gulshan Vinar, | Opp. Mahalaxmi Enclave, \ Jansath Road, Muzaffarnagar (U.P.) | Phone : 0131-2660440 (0), 2600503 (R) | website : www.shribalajibooks.com i NL Published by: ' SHRI BALAJI PUBLICATIONS - ‘email : sbjpub@gmail.com First edition: 2008 " Second edition : April 2008 : Third edition: April 2009 Seventh edition: April 2013 Eighth edition: April 2014 ©All Right Reserved with Author Price : = 480.00 Typeset by : Sun Creation Muzaffarnagar All the right reserved. No part of this publication may be reproduced, stored in 2 retrieval system cr transmitted, in any form or by any means, electronic, mechanical, photocopying, recording of otherwise, without the prior permission of the ‘authors and publisher. Any violationfbreach shall be taken into legal action. Dedicated to the Lotus feet of Revered Guruji SHRI KESARAM JI MAHARAJ Advanced Problems in ORGANIC CHEMISTRY It is a matter of great pleasure for me to present the eighth edition of “Advanced Problems in Organic Chemistry for JEE” before JEE aspirants. During my teaching experience, I felt that the facts may be made more and more clear to the students through problematic approach. Although an ‘ocean of material in Organic Chemistry is available with the students, yet the approach to design the problems has been changed in recent years and if one tries to swim in this ocean, it will be a very difficult task. To make the students more familiar with trends and tricks how to solve problems, the present problem book has been presented. In the current scenario of stiff competition especially for JEE, one must be clear that almost all the sincere applicants are well equipped with the facts of subject, yet the winner is one who knows how to use these equipments with accuracy and efficiency. AS an experienced teacher, I would like to suggest students three golden rules toscore high in OrganicChemistry: 1. Don'tgetbehind 2, Workoutanumber ofproblems of differenttypes 3. Revise through short notes / learning chart. Thope that the present book will cater to the needs of JE aspirants & as, a matter of fact, they will enjoy the present venture and I would feel rewarded if this book is found helpful to the students and teachers in real terms. All attempts have been made to make the book error free however a few misprints may inadvertently creep. J acknowledge the blessing and support of my mother Smt. Raj Kanwar, father Shri B.S. Chouhan, brother Dr. VS. Chouhan, my wife and daughter, They inspired meal the time during the preparation of this book. The support and valuable suggestions from my colleagues especially Mr. N. Avasthi, Mr. VX. Jaiswal, Mr. Nitin Jain, Mr. N.K. Sethia, Mr. Vikash Gupta, Mr. Pankaj Joshi, Dr. S. Kothari, Mr. Vineet Khatri, Mr. Ashish Mishra, Mr. Manish Arora, Mr. Govind Khandelwal, Mr. Rahul Pareek, Mr. Rahul Malav, Mr. Akshay Choudhary, Mr. Hanuman Sahay, Mrs. Neha Joshi, Mrs, Neetu Jha, Mr. Kamlesh Gupta, Mr. Kumud Ranjan and Mr. KD. Tiwari are highly acknowledged. I also pay my sincere thanks to all the esteemed members of M/s Shri Balaji Publications in bringing out this book in such anice form. In the last, constructive criticism and valuable suggestions from the readersaremost welcometo make the bookmore useful. M.S, CHOUHAN email: mahen_chouhan@yahoo.com Mob.(Only for SMS) : 09828025625 A few words to the JEE Aspi Dear JEE aspirants, | hope that this collection of problems will surely help you during your preparation for JEE. In this book, each chapter consists of two levels : Level 1 - includes the problems having only one option correct. ‘These problems are based on different facts and their twists. Level 2 - includes unique approach which may be used to solve the problems altogether different from the prevailing trend followed by JEE, These approaches will undoubtedly help you in the quick revision of the key facts and their applications. 1 wish all of you a grand success in the ensuing Joint Entrance Examination. Your valuable suggestions and constructive criticism for the betterment of the book are welcome. M.S, Chouhan e-mail : mahen_chouhan@yahoo.com eneral Organic Chemistry ~~ Isomerism (Structural & Stereoisomerism) [547 TAllo Hatides (substitution Reaction) Alkyl Halides (Elimination Reaction) ——————[—[—_———— Alkyt Halides itheir Derivatives’ ‘| S05] —— awa] CEN Practical Organic Chemistry "ear [Ga Taoneeais [is JuuracNames ss O™OC~—SS How many 2° Hydrogen atoms are present in the given following compound ? Son @2 5 oO7 @s Identify which functional group are Not present in the given following compound ? 9 NH oO (a) Ketone (b) Ester (¢) Amide (@) Ether Correct energy profile for amine inversion and hybridization of nitrogen in transition state is: tt = wh b T= WUT (a) ®) @ 0) @) “o ®B @ L____, L_____, 4 s A se © @ /\ ® ) a ® L___, L___, o Gio Gi Compare the heats of combustion of above compounds: @ O >> Gi) ©) @>G)>G © G>@> Gi @ Gi) > Gi) > 0 Which of the following is not a resonance structure of the others ? 9 9 9 Z . = @ © o @ Rank the hydrogen atoms (Hq, Hy, H) in the following molecule according to their acidic strength. HH @a>b>c (b)b>a>c © b>e>a @c>b>a ° I CHy —C—0-— CH; ‘Compare the bond lengths a and b. (@a=b @) b>a @b © cf @) Dun Diacone lactone frlactone Sclactam ‘The functional groups present in Cortisone are : HOH, ©. is och, 9 Cortisone (a) Ether, alkene, alcohol (b) Alcohol, ketone, alkene, ether © Alcohol, ketone, amine (© Ether, amine, ketone Select the acid with the highest K, ((e., lowest pK). Oo Oo Oo (@) W367 “OH py Cl ©, Oa Most stable carbocation among the given example is : CH @ @ L—F © ANY e © CO-% (@ cH, Set the following in increasing order of their pK values. ° ° I II @) Cs 0-H @) CH; —C—O—H — @) CH; —OH oO @y 99 a}xdst0 racine rofsssilig os “0 fir om msl < Td) vo 19. Circle represents most tbat, atoms,in these molecule. Which of. che llowine 5} correct Gree anne i ft 27. Se ted bond angl hevcarteo ase! urd: to their ok trot the lowest ee (3 Sa “B: a 4 beat) ¢ Bites oc a KO) “ ie) ia oy N @ oe at f < Ay tig Qxeons nojeorh)s cod wash ko ayameo = aad

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