ISBN 81-265-5582-3 9 788126 555826 PROBLEMS IN ORGANIC CHEMISTRY PROBLEMS IN ORGANIC CHEMISTRY Dr. K. Singh K. Singh Vision Classes, Patna Problems in Organic Chemistry Copyright © 2015 by Wiley India Pvt. Ltd., 4435-36/7, Ansari Road, Daryaganj, New Delhi-110002. Cover Image: stuartbur/iStockphoto All rights reserved. No part of this book may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording or scanning without the written permission of the Publisher. Limits of Liability: While the publisher and the author have used their best efforts in preparing this book, Wiley and the author make no representation or warranties with respect to the accuracy or completeness of the contents of this book, and specifically disclaim any implied warranties of merchantability or fitness for any particular purpose. There are no warranties which extend beyond the descriptions contained in this paragraph. No warranty may be created or extended by sales representatives or written sales materials. Disclaimer: The contents of this book have been checked for accuracy. Since deviations cannot be precluded entirely, Wiley or its author cannot guarantee full agreement. As the book is intended for educational purpose, Wiley or its author shall not be responsible for any errors, omissions or damages arising out of the use of the information contained in the book. This publication is designed to provide accurate and authoritative information with regard to the subject matter covered. It is sold on the understanding that the Publisher is not engaged in rendering professional services. Trademarks: All brand names and product names used in this book are trademarks, registered trademarks, or trade names of their respective holders. Wiley is not associated with any product or vendor mentioned in this book. Other Wiley Editorial Offices: John Wiley & Sons, Inc. 111 River Street, Hoboken, NJ 07030, USA Wiley-VCH Verlag GmbH, Pappellaee 3, D-69469 Weinheim, Germany John Wiley & Sons Australia Ltd, 42 McDougall Street, Milton, Queensland 4064, Australia John Wiley & Sons (Asia) Pte Ltd, 1 Fusionpolis Walk #07-01 Solaris, South Tower Singapore 138628 John Wiley & Sons Canada Ltd, 22 Worcester Road, Etobicoke, Ontario, Canada, M9W 1L1 Edition: 2015 ISBN: 978-81-265-5582-6 ISBN: 978-81-265-8216-7 (ebk) www.wileyindia.com Printed at: PREFACE Organic Chemistry is understood by reading the textbook, listening to lectures and memorizing name reactions with reagents. But perhaps most importantly, it is learnt by doing, that is, solving problems. It is not uncommon for students who have performed below expectation in JEE to explain that they honestly thought they understood the text and lectures. The diffi culty, however, lies in applying, generalizing, and extending the specifi c reactions and mechanisms they have “memorized” to the solution of a very broad array of related problems. In doing so, students will begin to “internalize” Organic Chemistry to develop an intuitive feel for, and appreciation of, the underlying logic of the subject. Acquiring that level of skill requires but goes far beyond rote learning. It is the ultimate process by which one learns to manipulate the myriad of reactions and, in time, gains a predictive power that will facilitate solving new problems. Mastering Organic Chemistry is challenging. It demands memorization, but then requires application of those facts to solve real problems. It features a highly logical structural hierarchy and builds upon a cumulative learning process. The requisite investment in time and effort, however, can lead to the development of a sense of self-confi dence in the subject, an intellectually satisfying experience, indeed. Many excellent textbooks are available to explain the theory of Organic Chemistry; all provide extensive exercises. Better performing students, however, consistently ask for additional exercises. It is the purpose of this book, then, to provide supplementary problems and their solutions that reinforce and extend those textbook exercises. This book has reached its destination in fi ve years; three years used in collection of problems chapter-wise and two years for correction/eliminating errors. I have designed this book in such a manner that it will be useful for JEE aspiring students. If you go through previous years’ JEE problems, you will fi nd that objective type questions have subjective nature, that is why it was decided to write an objective pattern book in a subjective way. The beauty of this book is in the solutions, which are at par with international level treatment. Each and every question has detailed solution with reaction sequence, bond cleavage and formation of products. The book has separate chapters for Substitution and Elimination reaction and Carbonyl alpha-Substitution and Carbonyl Condensation reactions, because JEE has always been framing problems from these chapters. Arrangement is according to classical functional group organization, with each group typically divided into Reactions, Conversions and Mechanisms. To emphasize the vertical integration of the subject, problems in later chapters heavily draw upon and integrate reactions learned in earlier chapters. It is desirable, but impossible, to write a problem book that is completely text-independent. Most problems will follow a similar developmental sequence, progressing from alkane/alkene/alkyne to aromatic to aldehyde/ketone to carboxylic acid to enol/enolate to amine chemistry. But within the earlier domains, placement of the basics, stereochemistry, S /E N mechanisms, and other functional groups varies considerably. The sequence is important because it establishes the concepts and reactions that can be utilized in subsequent problems. It is the intent of this problem book to follow a consensus sequence that complements a broad array of Organic Chemistry textbooks. Consequently, instructors utilizing a specifi c textbook may on some occasion offer their students guidance on the corresponding problem book chapter and select problems for practice. FFMM -- CCooppyy..iinndddd vv 88//1177//22001155 55::4422::3366 PPMM vi PREFACE I acknowledge the blessings and support of my mother Smt. Tileshwari Devi, father Shri Triveni Singh, wife Mrs. Sarika Singh and sons, Aayushman and Shauryaman. I would like to thank Dr. Sarika Mehta Jain for her unconditional support to make this an error-free book. She spent a lot of time on this book, and solved each and every problem to ensure authentic and error free solutions. I can say without any hesitation that she is the mother of this book, without her support this book would have never reached to my students, readers and teachers. I also sincerely thank all the members of Wiley India team and especially Paras Bansal, Anjali Chadha and Seema Sajwan in bringing out this book in such a nice form. It is all made possible by the grace of God Almighty. I devote this book to the feet of God. At the end, constructive criticism and valuable suggestions from the readers are most welcome to make the book more useful. Dr. K. Singh [email protected] FFMM -- CCooppyy..iinndddd vvii 88//1177//22001155 55::4422::3377 PPMM ABOUT THE AUTHOR Dr K. Singh has done his post-graduation in Chemistry with special paper in Organic Chemistry and his PhD in Water Pollution from Veer Kunwar Singh University, Ara, Bihar. He is an accomplished faculty in Chemistry, imparting quality education to JEE aspirants across north India. He has a vast teaching experience of more than 19 years and has taught more than 60,000 students. He has churned out thousands of successful students in JEE, many of whom attained top hundred ranks and studied in institutes of their choice. Many of these students are doing exceedingly well in the fi eld of research and in corporate sector. He is one of the very few faculties from Bihar who had the privilege of teaching at Kota in early days. He then went on to establish the fi rst Coaching Institute at Patna, Bihar, which is based on Kota teaching pattern. As a leading educationist of Patna, he very successfully stopped the migration of the students from Bihar to Kota. Dr K. Singh is a member of American Chemical Society and has been conferred with many awards. Some of which are: “Bharat Gaurav Award” by World Economic Progress Society; Rashtriya Siksha Ratna Award” by I.E.D.R.A. and “Bhojpuri Academy Samman” by Govt. of Bihar. He has also participated in the “National Conference on Excellence in Higher Education”. His name is counted among the most successful and respected faculty in the world of JEE coaching. FFMM -- CCooppyy..iinndddd vviiii 88//1177//22001155 55::4422::3388 PPMM FFMM -- CCooppyy..iinndddd vviiiiii 88//1177//22001155 55::4422::3388 PPMM
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