Wiley's Solomons, Fryhle & Snyder Organic Chemistry For Jee (Main & Advanced) 3RD Edition M.S. Chouhan Full Chapters Included
Wiley's Solomons, Fryhle & Snyder Organic Chemistry For Jee (Main & Advanced) 3RD Edition M.S. Chouhan Full Chapters Included
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for JEE (MAIN & ADVANCED)
2020
Highlights of the Book
Solomons
About the Book
This adapted version of one of the world's most well-known books on
• JEE syllabus completely covered. Fryhle
Organic Chemistry combines the Solomons, Fryhle and Snyder’s • Additional topics in textual and tabular form provided within the Snyder
approach to Organic Chemistry with JEE (Main & Advanced) chapter to clarify basic concepts.
requirements. The book has been reorganized based on the challenges • Three new chapters added based on the important topics of
faced by the students preparing for JEE (Main & Advanced) in terms of carbenes, nitrenes and polymers covered in the syllabus of JEE.
practice problems and clarity of concepts. The relevance to JEE is • Various solved examples other than the ones already present in
Solomons|Fryhle|Snyder
Chemistry
Organic
enhanced by elaborating concepts related to the syllabus, removing the original book provided for practice, covering all types of JEE
irrelevant topics and addition of JEE specific problems at the end of each questions.
chapter. Furthermore, the book • Irrelevant chapters/sections removed to present a concise text.
• Focuses on the three problem areas of Organic Chemistry – problem- • Illustrations and challenging problems bring out the emphasis of
solving, visualization of structures and understanding of mechanisms. the high-quality text.
ORGANIC
• Concept maps provided for each chapter to summarize the
• Contains well-illustrated reactions with elaborate and stepwise reactions and concepts for last-minute revision.
explanation of their mechanisms.
• End-of-Chapter exercises, in addition to thought –provoking
• Aids easy learning by summarizing various key concepts in the form of subjective questions, contain all question-type as per JEE
concept maps, summary and review tools. requirement
ü Single-Correct Choice Type
New to this Edition
— Includes NTA-conducted JEE Main 2019 (Jan) Chemistry
papers. Solutions available at
https://www.wileyindia.com/current-year-solved-paper.
ü Multiple-Correct Choice Type
ü Linked Comprehension Type
ü Integer Type
ü Matrix-Match Type
• Answers to selected problems at the end of the book
CHEMISTRY
• Answer key provided for all objective questions
• Chapter-wise solved JEE (Advanced) questions (2011-2017) for JEE (Main & Advanced)
• Includes solved JEE Advanced 2018 Chemistry paper
Visit us at https://www.wileyindia.com/resources/
Chouhan
Visit us at www.jee.wileymaestro.com
Scan the QR code with
your smart phone THIRD
to access
l Useful JEE Resources
ISBN 978-81-265-9832-8 EDITION
l Solutions to Practice and Review Problems
Wiley India Pvt. Ltd.
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Solomons|Fryhle|Snyder
Organic Chemistry
For JEE (Main & Advanced)
THIRD EDITION
Solomons|Fryhle|Snyder
Organic Chemistry
For JEE (Main & Advanced)
THIRD EDITION
Solomons, Fryhle and Snyder Organic Chemistry for JEE (Main & Advanced)
Third Edition
Copyright © 2019 by Wiley India Pvt. Ltd., 4436/7, Ansari Road, Daryaganj, New Delhi-110002.
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. This book is an adaptation of Organic Chemistry, 11/e by T. W. Graham Solomons, Craig B. Fryhle and
Scott A. Snyder (ISBN: 978-81-265-5684-7). All rights remain with their respective holders.
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.
“Why do these topics matter?” is a new feature that bookends each chapter with
a teaser in the opener and a captivating example of organic chemistry in the closer.
The chapter opener seeks to whet the student’s appetite both for the core chemistry
in that chapter as well as a prize that comes at the end of the chapter in the form of
a “Why do these topics matter?” vignette. These new closers consist of fascinating
nuggets of organic chemistry that stem from research relating to medical, environ-
mental, and other aspects of organic chemistry in the world around us, as well as the
history of the science. They show the rich relevance of what students have learned
to applications that have direct bearing on our lives and wellbeing. For example, in
Chapter 6, the opener talks about the some of the benefits and drawbacks of mak-
ing substitutions in a recipe, and then compares such changes to the nucleophilic
displacement reactions that similarly allow chemists to change molecules and their
properties. The closer then shows how exactly such reactivity has enabled scientists
to convert simple table sugar into the artificial sweetener Splenda which is 600 times
as sweet, but has no calories!
Laying the foundation earlier Certain tools are absolutely key to success in organic
chemistry. Among them is the ability to draw structural formulas quickly and correctly.
v
In this edition, we help students learn these skills even sooner than ever before by
moving coverage of structural formulas and the use curved arrows earlier in the text
(Section 3.5). We have woven together instruction about Lewis structures, covalent
bonds, and dash structural formulas, so that students build their skills in these areas
as a coherent unit, using organic examples that include alkanes, alkenes, alkynes, and
alkyl halides. One could say that it’s a “use organic to teach organic” approach.
Getting to the heart of the matter quicker Acid-base chemistry, and electro-
philes and nucleophiles are at the heart of organic chemistry. Students cannot
master the subject if they do not have a firm and early grasp of these topics. In
this edition, we cut to the chase with these topics earlier in Chapter 3 than ever
before, providing a streamlined and highly efficient route to student mastery of
these critical concepts.
Improving a core area: substitution reactions All organic instructors know how
important it is for their students to have a solid understanding of substitution
reactions. This is one reason our text has proven its lasting value. In this edition we
have even further enhanced the presentation of substitution reactions in several
ways, including a revised introduction of SN1 reactions (Section 6.10) through the
classic hydrolysis experiments of Hughes, and a newly organized presentation of
solvent effects on the rate of substitution reactions.
Maintaining an eye for clarity With every edition we improve the presentation of
topics, reactions, and diagrams where the opportunity arises. This edition includes
improved mechanism depictions for aromatic sulfonation and thionyl chloride sub-
stitution.
vi
Practice Problems Students need ample opportunities to practice and apply their
new found strategies for solving organic chemistry problems. We’ve added to our
rich array of in-text Practice Problems to provide students with even more oppor-
tunities to check their progress as they study. If they can work the practice problem,
they should move on. If not, they should review the preceding presentation.
SOLVED PROBLEMS
Solved Problem 11.2 model problem solving strategies.
Which reagents would you use to accomplish the follow- Answer
ing transformations?
(a) To oxidize a primary alcohol to a carboxylic acid,
O use (1) potassium permanganate in aqueous base,
OH (a) OH followed by (2) H3O+, or use chromic acid (H2CrO4).
(b) To reduce a carboxylic acid to a primary alcohol, use
(b) LiAlH4.
(c) To oxidize a primary alcohol to an aldehyde, use
O the Swern oxidation or pyridinium chlorochromate
OH (c) H (PCC).
(d) To reduce an aldehyde to a primary alcohol, use
(d) NaBH4 (preferably) or LiAlH4.
PRACTICE PROBLEMS
Practice Problem 11.3 provides opportunities to
Show how each of the following transformations could be accomplished: check progress.
O O
OH ? H OH ? OH
(a) (b)
A Mechanism for the Reaction Understanding mechanisms and the ability to recog-
nize patterns among them is a key component in determining student success in organ-
ic chemistry. We provide A Mechanism for the Reaction boxes that show step-by-step
details about how reactions take place so that students have the tools to understand
rather than memorize organic reactions.
vii
A MECHANISM FOR THE
A MECHANISM FOR THE REACTION Hydrogen Atom Abstraction
REACTION Stepped out
General Reaction
reactions with just the right
amount of detail provides the X + H R X H + R
Key Ideas as Bullet Points The amount of content covered in organic chemistry can
be overwhelming to students. To help students focus on the most essential topics, key
ideas are emphasized as bullet points in every section. In preparing bullet points, we
have distilled appropriate concepts into simple declarative statements that convey
core ideas accurately and clearly. No topic is ever presented as a bullet point if its
integrity would be diminished by oversimplification, however.
“How to” Sections Students need to master important skills to support their con-
ceptual learning. “How to” Sections throughout the text give step-by-step instruc-
tions to guide students in performing important tasks, such as using curved arrows,
drawing chair conformations, planning a Grignard synthesis, determining formal
charges and writing Lewis structures.
The Chemistry of . . . . Virtually every instructor has the goal of showing students how
organic chemistry relates to their field of study and to their everyday life experience.
The authors assist their colleagues in this goal by providing boxes titled “The Chemistry
of . . .” that provide interesting and targeted examples that engage the student with
chapter content.
Summary and Review Tools At the end of each chapter, Summary and Review
Tools provide visually oriented roadmaps and frameworks that students can
use to help organize and assimilate concepts as they study and review chapter
content. Intended to accommodate diverse learning styles, these include Synthetic
H X X X
H R2 X R2
HX X2
R1 C C R2 C C C C R1 C C R2
(2nd molar (2nd molar
equivalent) R1 X R1 X equivalent)
H X X X
(If R1 in alkyne is H
then addition is
Markovnikov) X2
HX
(1st molar (1st molar
equivalent) equivalent)
• Hydrohalogenation
• Halogenation
• Hydrogenation C C
R1 R2 (1) KMnO4, HO , heat (2) H3O
• Carbene Addition
or
• Ozonolysis
(1) X2 (1) X2 (1) O3 (2) HOAc
• Potassium Permanganate Cleavage
• Alkyne Synthesis by Double E2 (2) NaNH2 (2) NaNH2
(2 equiv.), (2 equiv.),
heat heat
H2, (1) Na, EtNH2
Lindlar’s or
R1 R2 *(1) O3 R1 R2 P-2 catalyst
(2) NH4Cl R1 H *(1) KMnO4, R1 OH
HO , heat
C O O C C C C C C O O C
(2) Me2S (Z) (E) (2) H3O
H H H H H R2 HO R2
H2, catalyst
(Pt, Pd, Rh, Ni)
CH2I2, Zn(Cu) CH2I2, Zn(Cu)
(or other methods) (or other methods)
H H
R1 C C R2
R1 R2 R1 H
H H H H H R2
*If R1 is H, then alkene ozonolysis generates
formaldehyde and KMnO4 generates CO2.
If the alkene is disubstituted at one end, a ketone
results from cleavage by either ozonolysis or KMnO4.
viii
[C O N C E P T M A P ]
Conformers
(Section 5.8)
are
can have
Ring strain
Different potential energies (Section 5.10)
of conformers can among conformers
be represented by is a function of is caused by
and
Conformer potential Torsional strain Angle strain
energy diagrams (Section 5.8) (Section 5.10)
(Section 5.9)
are a plot of is caused by and loss of is caused by
COVERAGE
Throughout the book, we have streamlined or reduced content to match the modern
practice of organic chemistry, and we have provided new coverage of current reactions,
while maintaining our commitment to an appropriate level and breadth of coverage.
ix
lend themselves to introducing several important topics that students need early
in the course: (1) curved arrow notation for illustrating mechanisms, (2) the
relationship between free-energy changes and equilibrium constants, and (3) the
importance of inductive and resonance effects and of solvent effects.
In Chapter 3 we present the first of many “A Mechanism for the Reaction” boxes,
using an example that embodies both Brønsted-Lowry and Lewis acid-base
principles. All throughout the book, we use boxes like these to show the details of
key reaction mechanisms. All of the Mechanism for the Reaction boxes are listed in
the Table of Contents so that students can easily refer to them when desired.
A central theme of our approach is to emphasize the relationship between
structure and reactivity. This is why we choose an organization that combines the
most useful features of a functional group approach with one based on reaction
mechanisms. Our philosophy is to emphasize mechanisms and fundamental
principles, while giving students the anchor points of functional groups to apply
their mechanistic knowledge and intuition. The structural aspects of our approach
show students what organic chemistry is. Mechanistic aspects of our approach show
students how it works. And wherever an opportunity arises, we show them what it
does in living systems and the physical world around us.
In summary, our writing reflects the commitment we have as teachers to do the
best we can to help students learn organic chemistry and to see how they can apply
their knowledge to improve our world. The enduring features of our book have
proven over the years to help students learn organic chemistry.
Preface to the Adapted Version
This book is dedicated to the lotus feet of Revered Guruji
SHRI KESARAM JI MAHARAJ
It is a matter of great pleasure for me to present the second edition of the book before
engineering aspirants. This book was written because I felt the need for a textbook
that corresponds closely to the course that I teach. Although the book is organized
along tried-and- true functional-group lines, it contains some unique features that
have served me well in both my teaching and understanding of Organic Chemistry.
My four major concerns in both the initial writing and the revision of this text
were readability, presentation, organization, and accuracy. In the current scenario of
stiff competition especially for engineering entrances, one must be clear that almost
all the sincere applicants are well equipped with the facts of subject; yet, the winner
is the one who knows how to use these facts with accuracy and efficiency. As an
experienced teacher, I would like to suggest students three golden rules to score high
in Organic Chemistry:
I hope that the present book will cater to the needs of engineering aspirants.
As a matter of fact, they will enjoy the present venture and I would feel rewarded
if this book is helpful for the students and teachers in real terms. All efforts have
been made to make the book error-free; however, a few misprints may inadvertently
creep.
I acknowledge the blessing and support of my mother Smt. Raj Kanwar,
father Shri B.S. Chouhan, brother Dr. V. S. Chouhan, wife Ms. Meena Chouhan and
daughter. They inspired me all the time during the preparation of this book.
The support and valuable suggestions from Mr. V.K. Jaiswal, Mr. N. Avasthi,
Mr. Akshay Chawdhary, Dr. S. Kothari, Mr. Navneet Jethwani, Ms. Neha
Joshi, Mr. Ashish Mishra, Mr. Kumud Ranjan, Mr. Mohit Sayal, Mr. Hanuman
Prasad Sahay, Mr. Vineet Khatri, Mr. Govind Khadelwal, Mr. Manish
Arora, Mr. Rahul Malay, Mr. Rahul Pareek, Mr. Divyesh Tiwari, Mr. Omkar
Kelapure, Mr. Mayank Pareek, Mr. Gurpreet Singh, Mr. Yogesh Jain, Ms.
Anjana Kamal, Mr. Anit Chaudhry, Mr. Shaliwahan Singh Rathore and
Mr. Kishore Kilani, are highly acknowledged. I also pay my sincere thanks to all
the esteemed members of Wiley India and specially Ms. Anjali Chadha, Ms. Seema
Sajwan and Mr. Rakesh Poddar in bringing out this book in such a nice form.
In the end, constructive criticism and valuable suggestions from the readers are
most welcome to make the book more useful.
M.S.Chouhan
(MSC Sir)
Email: [email protected]
Mobile: 9828025625
xi
xiii
and Bristol-Myers-Squibb predoctoral fellow.While there,he co-authored the graduate
textbook Classics in Total Synthesis II with his doctoral mentor. Scott was then an
NIH postdoctoral fellow in the laboratories of E. J. Corey at Harvard University
before assuming his current position in 2006. His research interests lie in the arena
of natural products total synthesis, especially in the realm of unique polyphenols
and halogenated materials, and to date he has trained more than 60 students at the
high school, undergraduate, graduate, and postdoctoral levels and co-authored more
than 40 research and review articles. Scott has received a number of awards and
honors, including a Camille and Henry Dreyfus New Faculty Award, Amgen New
Faculty and Young Investigator Awards, Eli Lilly New Faculty and Grantee Awards,
a Bristol-Myers Squibb Unrestricted Grant Award, an NSF CAREER Award, an
Alfred P. Sloan Foundation Fellowship, a DuPont Young Professor Award, and
an Arthur C. Cope Scholar Award from the American Chemical Society. He has
also received recognition for his teaching through a Cottrell Scholar Award from
the Research Corporation for Science Advancement and a Columbia Presidential
Teaching Award. He is a member of the international advisory board for The
Chemical Record and the editorial board of Chirality. He lives north of New York
City with his wife Cathy where he enjoys gardening, cooking, and watching movies.
About the Adapting Author
Mahendra Singh Chouhan (MSC Sir) is a renowned name in the realm of Organic
Chemistry. Though a Chemical engineer from Mumbai University, he has great
passion for the subject that led him to impart guidance to engineering aspirants on
a regular basis. His in-depth knowledge and vast teaching experience has helped
innumerable students to achieve their dream of excelling in engineering and other
such tough challenges.
He has launched a website to extend the benefits of his expertise beyond the
geographical barriers to all those who dare to dream and seek—www.winvall.com
and www.shivwin.com. The website provides expert guidance in all areas of the
subject in a most skillful manner. There are quizzes, challenging questions, notes,
e-books, videos, etc. This website is a complete guide in itself for organic chemistry
and has been designed for engineering, keeping in mind CBSE syllabus and various
other syllabi. Highly recommended for high flyers!
xv
To the Student
Contrary to what you may have heard, organic chemistry Organic chemistry is best assimilated through the
does not have to be a difficult course. It will be a rigorous fingertips by writing, and not through the eyes by
course, and it will offer a challenge. But you will learn simply looking, or by highlighting material in the
more in it than in almost any course you will take—and text, or by referring to flash cards. There is a good
what you learn will have a special relevance to life and reason for this. Organic structures, mechanisms,
the world around you. However, because organic chem- and reactions are complex. If you simply examine
istry can be approached in a logical and systematic way, them, you may think you understand them thor-
you will find that with the right study habits, mastering oughly, but that will be a misperception. The reac-
organic chemistry can be a deeply satisfying experience. tion mechanism may make sense to you in a certain
Here, then, are some suggestions about how to study: way, but you need a deeper understanding than
this. You need to know the material so thoroughly
1. Keep up with your work from day to day— that you can explain it to someone else. This level
never let yourself get behind. Organic chemistry of understanding comes to most of us (those of
is a course in which one idea almost always builds on us without photographic memories) through writ-
another that has gone before. It is essential, therefore, ing. Only by writing the reaction mechanisms do
that you keep up with, or better yet, be a little ahead we pay sufficient attention to their details, such
of your instructor. Ideally, you should try to stay one as which atoms are connected to which atoms,
day ahead of your instructor’s lectures in your own which bonds break in a reaction and which bonds
class preparations. The lecture, then, will be much form, and the three-dimensional aspects of the
more helpful because you will already have some structures. When we write reactions and mech-
understanding of the assigned material. Your time anisms, connections are made in our brains that
in class will clarify and expand ideas that are already provide the long-term memory needed for success
familiar ones. in organic chemistry. We virtually guarantee that
2. Study material in small units, and be sure that your grade in the course will be directly propor-
you understand each new section before you go tional to the number of pages of paper that your
on to the next. Again, because of the cumulative fill with your own writing in studying during the
nature of organic chemistry, your studying will be term.
much more effective if you take each new idea as it 5. Learn by teaching and explaining. Study with
comes and try to understand it completely before you your student peers and practice explaining concepts
move on to the next concept. and mechanisms to each other. Use the exercises
3. Work all of the in-chapter and assigned problems. your instructor may assign as vehicles for teaching
One way to check your progress is to work each of and learning interactively with your peers.
the in-chapter problems when you come to it. These 6. Use the answers to the problems in the Study
problems have been written just for this purpose and Guide in the proper way. Refer to the answers
are designed to help you decide whether or not you only in two circumstances: (1) When you have fin-
understand the material that has just been explained. ished a problem, use the Study Guide to check your
You should also carefully study the Solved Problems. answer. (2) When, after making a real effort to solve
If you understand a Solved Problem and can work the problem, you find that you are completely stuck,
the related in-chapter problem, then you should then look at the answer for a clue and go back to
go on; if you cannot, then you should go back and work out the problem on your own. The value of
study the preceding material again. Work all of the a problem is in solving it. If you simply read the
problems assigned by your instructor from the end problem and look up the answer, you will deprive
of the chapter, as well. Do all of your problems in a yourself of an important way to learn.
notebook and bring this book with you when you go
to see your instructor for extra help. 7. Use molecular models when you study. Because
of the three-dimensional nature of most organic
4. Write when you study. Write the reactions, mech- molecules, molecular models can be an invaluable
anisms, structures, and so on, over and over again. aid to your understanding of them.
xvii
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