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Wiley's Solomons, Fryhle & Snyder Organic Chemistry for JEE (Main & Advanced) 3rd Edition by M.S. Chouhan is a comprehensive resource tailored for JEE preparation, covering the complete syllabus and including new chapters on carbenes, nitrenes, and polymers. The book emphasizes problem-solving, visualization, and understanding mechanisms, with numerous solved examples and practice problems to aid learning. It also features concept maps and end-of-chapter exercises aligned with JEE question types to enhance student comprehension and readiness for exams.

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100% found this document useful (1 vote)
634 views125 pages

Wiley's Solomons, Fryhle & Snyder Organic Chemistry For Jee (Main & Advanced) 3RD Edition M.S. Chouhan Instant Download

Wiley's Solomons, Fryhle & Snyder Organic Chemistry for JEE (Main & Advanced) 3rd Edition by M.S. Chouhan is a comprehensive resource tailored for JEE preparation, covering the complete syllabus and including new chapters on carbenes, nitrenes, and polymers. The book emphasizes problem-solving, visualization, and understanding mechanisms, with numerous solved examples and practice problems to aid learning. It also features concept maps and end-of-chapter exercises aligned with JEE question types to enhance student comprehension and readiness for exams.

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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
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• Includes solved JEE Advanced 2018 Chemistry paper

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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.

Other Wiley Editorial Offices:


John Wiley & Sons, Inc. 111 River Street, Hoboken, NJ 07030, USA
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John Wiley & Sons Canada Ltd, 22 Worcester Road, Etobicoke, Ontario, Canada, M9W 1L1

Third Edition: 2017


Reprint: 2019
ISBN: 978-81-265-9832-8
ISBN: 978-81-265-8874-9 (ebk)
www.wileyindia.com
Preface to the Original Edition
“IT’S ORGANIC CHEMISTRY!”
That’s what we want students to exclaim after they become acquainted with our subject.
Our lives revolve around organic chemistry, whether we all realize it or not. When we
understand organic chemistry, we see how life itself would be impossible without it,
how the quality of our lives depends upon it, and how examples of organic chemistry
leap out at us from every direction. That’s why we can envision students enthusiastically
exclaiming “It’s organic chemistry!” when, perhaps, they explain to a friend or family
member how one central theme—organic chemistry—pervades our existence. We want
to help students experience the excitement of seeing the world through an organic lens,
and how the unifying and simplifying nature of organic chemistry helps make many
things in nature comprehensible.
Our book makes it possible for students to learn organic chemistry well and to
see the marvelous ways that organic chemistry touches our lives on a daily basis.
Our book helps students develop their skills in critical thinking, problem solving, and
analysis—skills that are so important in today’s world, no matter what career paths
they choose. The richness of organic chemistry lends itself to solutions for our time,
from the fields of health care, to energy, sustainability, and the environment. After all,
it’s organic chemistry!
Guided by these goals, and by wanting to make our book even more accessible to
students than it has ever been before, we have brought many changes to this edition.

NEW TO THIS EDITION


With this edition we bring Scott Snyder on board as a co-author. We’re very excited
to have Scott join our team. Scott brings a rich resource of new perspectives to the
book, particularly in the arena of complex molecule synthesis. Scott has infused new
examples and applications of exciting chemistry that help achieve our goals. In addi-
tion to adding his perspectives to the presentation of core chemistry throughout the
book, Scott’s work is manifest in most of this edition’s chapter openers and in all of
the chapter closers, couched in a new feature called “Why do these topics matter?”.

“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.

Striking a strong balance of synthetic methods Students need to learn methods


of organic synthesis that are useful, as environmentally friendly as possible, and that
are placed in the best overall contextual framework. In this edition we incorporate
the Swern oxidation (Section 11.4B), long held as a useful oxidation method and one
that provides a less toxic alternative to chromate ­oxidations in some cases. We also
restore coverage of the Wolff-Kishner reduction (Section 15.8C) and the Baeyer-Vil-
liger oxidation (Section 15.12), two methods whose importance has been proven
by the test of time. The chemistry of radical reactions has also been refocused and
streamlined by reducing thermochemistry content and by centralizing the coverage
of allylic and benzylic radical substitutions (including NBS reactions) in one chapter
(Sections 9.7 and 9.8), instead of distributing it between two, as before. The addition
of sulfuric acid to alkenes and the Kolbe reaction have been deleted from the text,
since these have little practical use in the laboratory.

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.

Showing how things work A mechanistic understanding of organic chemistry is key


to student success in organic chemistry. Mechanisms have always been central to the
book, and in this edition the authors have added a mechanistic framework for the
Swern and chromate alcohol oxidations (Section 11.4) by presenting elimination of
the carbinol hydrogen and a leaving group from oxygen as the common theme.

TRADITIONAL PEDAGOGICAL STRENGTHS


Solved Problems Knowing “where to begin” to solve organic chemistry problems
is one of the greatest challenges faced by today’s students. By modeling problem
solving strategies, students begin to understand the patterns inherent in organic
chemistry and learn to apply that knowledge to new situations. In this edition we
have added even more Solved Problems. They are usually paired with a related
Practice Problem.

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)

End-of-Chapter Problems As athletes and musicians know, practice makes perfect.


The same is true with organic chemistry. The End of Chapter problems, categorized
by topic, provide essential practice for students and help them build mastery of both
concepts and skills presented throughout the chapter. Many of the End of Chapter
problems are cast in a visual format using structures, equations, and schemes.
END-OF-CHAPTER
7.28 Give the IUPAC names for each of the following:
CH3 PROBLEMS are grouped
D
and labeled by topic. ­Students
(a) (d) H
and instructors can more easily
7.34 Outline a synthesis of phenylethyne from each of the
following: select problems for specific
Br Br
(b) (e) Br ­purposes.
H (a) (b)
Cl Cl
Br
O
(c) (f)
(c) (d)

7.29 Without consulting tables, arrange the following com-


pounds in order of decreasing acidity:
Pentane 1-Pentene 1-Pentyne 1-Pentanol
Dehydrohalogenation and Dehydration
7.35 Write a three-dimensional representation for the tran-
Synthesis sition state structure leading to formation of 2-methyl-
7.30 Outline a synthesis of propene from each of the following: 2-butene from reaction of 2-bromo-2-methylbutane with
(a) Propyl chloride sodium ethoxide.
(b) Isopropyl chloride 7.36 When trans-2-methylcyclohexanol (see the following
(c) Propyl alcohol reaction) is subjected to acid-catalyzed dehydration, the
(d) Isopropyl alcohol major product is 1-methylcyclohexene:

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

tools for students to understand Reactive Alkane Alkyl radical


radical intermediate
rather than memorize ­reaction intermediate (reacts further)
mechanisms Specific Example
Cl + H CH3 Cl H + CH3
Chlorine Methane Methyl radical
atom intermediate
(a radical) (reacts further)

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

SUMMARY AND REVIEW TOOLS Visually


oriented study tools accommodate diverse
[S U M M A R Y A N Dand Review
Summary R E Tools
V I E W T O O L S ]
learning styles. Synthetic Connections of Alkynes and Alkenes: II

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

Molecules that differ only by rotation


about sigma (s s ) bonds

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

Dihedral angle vs. Repulsive Hyperconjugative Deviation from ideal


potential energy dispersion stabilization bond angles
forces (Section 5.8)
result in involves
E

Steric hindrance Favorable overlap of


0 60 120 240 300 360
Degrees of Rotation u
420
(Section 5.8) occupied with
can be unoccupied of cyclohexane
represented orbitals can be
by represented by
Newman projection
formulas Chair conformational structures Boat
(Section 5.8) or
(Section 5.11)

can be used to show have


Axial positions
Eclipsed Staggered
and
conformations conformations and twist-boat
with substituted
groups (G) can be
and
G G
G
Equatorial positions
Anti or Gauche conformational
G structures

Connections, Concept Maps, Thematic Mechanism Review Summaries, and the


detailed Mechanism for the Reaction boxes already mentioned. We also provide
Helpful Hints and richly annotated illustrations throughout the text.

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.

• Chapters on carbonyl chemistry that are organized to emphasize mechanistic themes


of nucleophilic addition, acyl substitution, and reactivity at the a-carbon.

ORGANIZATION—An Emphasis on the Fundamentals


So much of organic chemistry makes sense and can be generalized if students
master and apply a few fundamental concepts. Therein lays the beauty of
organic chemistry. If students learn the essential principles, they will see that
memorization is not needed to succeed.
Most important is for students to have a solid understanding of structure—
of hybridization and geometry, steric hindrance, electronegativity, polarity, formal
charges, and resonance—so that they can make intuitive sense of mechanisms. It is
with these topics that we begin in Chapter 1. In Chapter 2 we introduce the families of
functional groups—so that students have a platform on which to apply these concepts.
We begin our study of mechanisms in the context of acid-base chemistry in
Chapter 3. Acid-base reactions are fundamental to organic reactions, and they

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:

1. Do not lag behind in schedule.


2. Work out a number of problems of different types.
3. Revise through short notes.

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

FM_FrontMatter.indd 11 3/20/2017 7:02:40 PM


About the Authors
T. W. GRAHAM SOLOMONS did his undergraduate work at The Citadel and
received his doctorate in organic chemistry in 1959 from Duke University where he
worked with C. K. Bradsher. Following this he was a Sloan Foundation Postdoctoral
Fellow at the University of Rochester where he worked with V. Boekelheide. In 1960
he became a charter member of the faculty of the University of South Florida and
became Professor of Chemistry in 1973. In 1992 he was made Professor Emeritus.
In 1994 he was a visiting professor with the Faculté des Sciences Pharmaceutiques
et Biologiques, Université René Descartes (Paris V). He is a member of Sigma Xi,
Phi Lambda Upsilon, and Sigma Pi Sigma. He has received research grants from
the Research Corporation and the American Chemical Society Petroleum Research
Fund. For several years he was director of an NSF-sponsored Undergraduate
Research Participation Program at USF. His research interests have been in the
areas of heterocyclic chemistry and unusual aromatic compounds. He has published
papers in the Journal of the American Chemical Society, the Journal of Organic
Chemistry, and the Journal of Heterocyclic Chemistry. He has received several
awards for distinguished teaching. His organic chemistry textbooks have been
widely used for 30 years and have been translated into French, Japanese, Chinese,
Korean, Malaysian, Arabic, Portuguese, Spanish, Turkish, and Italian. He and his
wife Judith have a daughter who is a building conservator and a son who is a
research biochemist.

CRAIG BARTON FRYHLE is Chair and Professor of Chemistry at Pacific Lutheran


University. He earned his B.A. degree from Gettysburg College and Ph.D. from
Brown University. His experiences at these institutions shaped his dedication to
mentoring undergraduate students in chemistry and the liberal arts, which is a pas-
sion that burns strongly for him. His research interests have been in areas relating
to the shikimic acid pathway, including molecular modeling and NMR spectrometry
of substrates and analogues, as well as structure and reactivity studies of shikimate
pathway enzymes using isotopic labeling and mass spectrometry. He has mentored
many students in undergraduate research, a number of who have later earned their
Ph.D. degrees and gone on to academic or industrial positions. He has participated
in workshops on fostering undergraduate participation in research, and has been
an invited participant in efforts by the National Science Foundation to enhance
undergraduate research in chemistry. He has received research and instrumentation
grants from the National Science Foundation, the M J. Murdock Charitable Trust,
and other private foundations. His work in chemical education, in addition to text-
book coauthorship, involves incorporation of student-led teaching in the classroom
and technology-based strategies in organic chemistry. He has also developed exper-
iments for undergraduate students in organic laboratory and instrumental analysis
courses. He has been a volunteer with the hands-on science program in Seattle
public schools, and Chair of the Puget Sound Section of the American Chemical
Society. His passion for climbing has led to ascents of high peaks in several parts of
the world. He resides in Seattle with his wife, where both enjoy following the lives
of their two daughters as they unfold in new places.

SCOTT A. SNYDER is Associate Professor of Chemistry at Columbia University. He


grew up in the suburbs of Buffalo NY and was an undergraduate at Williams College,
where he graduated summa cum laude in 1999, before pursuing his doctoral studies at
The Scripps Research Institute under the tutelege of K. C. Nicolaou as an NSF, Pfizer,

xiii
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Ethics - Lab Manual
First 2021 - Research Center

Prepared by: Dr. Williams


Date: July 28, 2025

Quiz 1: Interdisciplinary approaches


Learning Objective 1: Ethical considerations and implications
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Learning Objective 2: Learning outcomes and objectives
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 2: Diagram/Chart/Graph]
Learning Objective 3: Current trends and future directions
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Learning Objective 4: Study tips and learning strategies
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Learning Objective 5: Research findings and conclusions
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Key terms and definitions
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Key Concept: Case studies and real-world applications
• Key terms and definitions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 7: Diagram/Chart/Graph]
Important: Comparative analysis and synthesis
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Key terms and definitions
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Definition: Historical development and evolution
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 10: Diagram/Chart/Graph]
Exercise 2: Theoretical framework and methodology
Definition: Study tips and learning strategies
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Remember: Current trends and future directions
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 12: Practical applications and examples
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Fundamental concepts and principles
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Practice Problem 14: Key terms and definitions
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 15: Research findings and conclusions
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Practical applications and examples
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Example 17: Current trends and future directions
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 18: Key terms and definitions
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Problem-solving strategies and techniques
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 20: Diagram/Chart/Graph]
Review 3: Experimental procedures and results
Key Concept: Historical development and evolution
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Definition: Ethical considerations and implications
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Remember: Experimental procedures and results
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Note: Practical applications and examples
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Experimental procedures and results
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
[Figure 25: Diagram/Chart/Graph]
Practice Problem 25: Interdisciplinary approaches
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 26: Diagram/Chart/Graph]
Important: Critical analysis and evaluation
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Example 27: Critical analysis and evaluation
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 28: Historical development and evolution
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Practical applications and examples
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Unit 4: Ethical considerations and implications
Practice Problem 30: Interdisciplinary approaches
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 31: Diagram/Chart/Graph]
Key Concept: Problem-solving strategies and techniques
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
[Figure 32: Diagram/Chart/Graph]
Key Concept: Learning outcomes and objectives
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 33: Experimental procedures and results
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Assessment criteria and rubrics
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 35: Diagram/Chart/Graph]
Definition: Research findings and conclusions
• Theoretical framework and methodology
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 36: Diagram/Chart/Graph]
Key Concept: Assessment criteria and rubrics
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Best practices and recommendations
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Key Concept: Learning outcomes and objectives
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 39: Diagram/Chart/Graph]
Practice Problem 39: Best practices and recommendations
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 40: Diagram/Chart/Graph]
Summary 5: Statistical analysis and interpretation
Practice Problem 40: Case studies and real-world applications
• Theoretical framework and methodology
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Remember: Literature review and discussion
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Definition: Current trends and future directions
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 43: Diagram/Chart/Graph]
Key Concept: Fundamental concepts and principles
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 44: Comparative analysis and synthesis
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Experimental procedures and results
• Key terms and definitions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 46: Diagram/Chart/Graph]
Note: Experimental procedures and results
• Research findings and conclusions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Practice Problem 47: Statistical analysis and interpretation
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Important: Current trends and future directions
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 49: Best practices and recommendations
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 50: Diagram/Chart/Graph]
Practice 6: Best practices and recommendations
Remember: Practical applications and examples
• Experimental procedures and results
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Key Concept: Learning outcomes and objectives
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Definition: Problem-solving strategies and techniques
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Practice Problem 53: Experimental procedures and results
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 54: Key terms and definitions
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Practice Problem 55: Best practices and recommendations
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 56: Diagram/Chart/Graph]
Key Concept: Problem-solving strategies and techniques
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 57: Historical development and evolution
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Key terms and definitions
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 59: Study tips and learning strategies
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Exercise 7: Current trends and future directions
Note: Interdisciplinary approaches
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Key Concept: Theoretical framework and methodology
• Key terms and definitions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 62: Diagram/Chart/Graph]
Note: Historical development and evolution
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Experimental procedures and results
• Key terms and definitions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Definition: Fundamental concepts and principles
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Statistical analysis and interpretation
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Important: Comparative analysis and synthesis
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Definition: Key terms and definitions
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Practice Problem 68: Best practices and recommendations
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 69: Best practices and recommendations
• Current trends and future directions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Quiz 8: Assessment criteria and rubrics
Remember: Best practices and recommendations
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Remember: Theoretical framework and methodology
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Best practices and recommendations
• Assessment criteria and rubrics
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Key terms and definitions
• Problem-solving strategies and techniques
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Theoretical framework and methodology
• Study tips and learning strategies
- Sub-point: Additional details and explanations
- Example: Practical application scenario
[Figure 75: Diagram/Chart/Graph]
Practice Problem 75: Literature review and discussion
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Key Concept: Research findings and conclusions
• Comparative analysis and synthesis
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Theoretical framework and methodology
• Best practices and recommendations
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Practical applications and examples
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Research findings and conclusions
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Section 9: Fundamental concepts and principles
Note: Best practices and recommendations
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
[Figure 81: Diagram/Chart/Graph]
Practice Problem 81: Assessment criteria and rubrics
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 82: Literature review and discussion
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Comparative analysis and synthesis
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 84: Diagram/Chart/Graph]
Remember: Study tips and learning strategies
• Learning outcomes and objectives
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Definition: Research findings and conclusions
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
[Figure 86: Diagram/Chart/Graph]
Key Concept: Critical analysis and evaluation
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Remember: Current trends and future directions
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Key Concept: Best practices and recommendations
• Statistical analysis and interpretation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
Definition: Problem-solving strategies and techniques
• Theoretical framework and methodology
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice 10: Literature review and discussion
Practice Problem 90: Theoretical framework and methodology
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Important: Statistical analysis and interpretation
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Important: Comparative analysis and synthesis
• Fundamental concepts and principles
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Practice Problem 93: Best practices and recommendations
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Important: Assessment criteria and rubrics
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Definition: Study tips and learning strategies
• Current trends and future directions
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Practice Problem 96: Problem-solving strategies and techniques
• Practical applications and examples
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Remember: Historical development and evolution
• Critical analysis and evaluation
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Remember: Assessment criteria and rubrics
• Interdisciplinary approaches
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Note: Critical analysis and evaluation
• Historical development and evolution
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Exercise 11: Ethical considerations and implications
Note: Fundamental concepts and principles
• Literature review and discussion
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Example 101: Fundamental concepts and principles
• Case studies and real-world applications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
- Note: Important consideration
Formula: [Mathematical expression or equation]
Note: Research findings and conclusions
• Ethical considerations and implications
- Sub-point: Additional details and explanations
- Example: Practical application scenario
Formula: [Mathematical expression or equation]
[Figure 103: Diagram/Chart/Graph]
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