Student Study Guide and Solutions Manual for Brown's Organic Chemistry, 7th Edition

884 Pages·2013·41.556 MB·English

by  William H. Brown, Brent L. Iverson, Eric V. Anslyn, Christopher S. Foote

Student Study Guide and Solutions Manual for
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Student Study Guide and Solutions Manual
Organic Chemistry
SEVENTH EDITION
William H. Brown
Beloit College
Brent L. Iverson
University of Texas, Austin
Eric V. Ansiyn
University of Texas, Austin
Christopher S. Foote
University of California, Los Angeles
Prepared by
Brent L. iverson
University of Texas, Austin
aM CENGAGE
Learning
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© 2014 Cengage Learning ISBN-13: 978-1-285-05261-8
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____ This Student Study Guide is a companion to the seventh edition of Organic Chemistry by
William Brown, Brent Iverson, Eric Anslyn, and Christopher Foote. All of the problems from the
text have been reprinted in this guide, so there is no need to flip back and forth between the text and
the guide. Detailed, stepwise solutions to all of the problems are provided.
Molecules are three-dimensional and understanding the three-dimensionality of organic
chemistry is important for any student. This Student Study Guide has placed special emphasis on
stereochemistry, an important aspect of three-dimensional molecular structure. Throughout the
problems and answers, many of the molecules with chiral centers have the configuration explicitly
denoted using wedges and dashes to indicate location in space. When the configuration is not
specifically given, chiral centers are indicated by an asterisk (*). In addition, the stereochemical
outcome of every reaction is stated, whether the question calls for consideration of stereochemistry
or not.
There are two new and innovative features of this Student Study Guide. First, each
mechanistic step is identified as one of the relatively few fundamental mechanistic elements
introduced in the primer preceding Chapter 6. Providing such systematic and stepwise answers to
all of the mechanism questions will help students more easily identify the similarities and thereby
make connections between the mechanisms from different chapters. This revolutionary new
approach will help students understand as opposed to just memorize organic chemistry. The
second innovative feature new to this edition is the inclusion of organic chemistry roadmaps in all
of the chapters that introduce new reactions (for an example see Problem 7.29). Roadmaps are
effective study aides in which key functional groups are listed as locations, and specific reactions
are shown as the routes between them. Roadmaps help students collect and organize the different
reactions from multiple chapters in a two-dimensional format that is easy to understand and review.
These roadmaps help students “navigate” synthesis questions that involve multiple sequential
reactions, the type of problem that in our experience causes students the most difficulty.
Immediately following an end of chapter problem asking students to update their roadmap, we have
added new questions requiring students to utilize the roadmaps while navigating multi-step
transformations (for an example see Problem 7.30).
The material in this volume was reviewed for accuracy by William Brown, Brent Iverson
and Sheila Iverson. If you have any comments or questions, please direct them to Professor Brent
Iverson, Department of Chemistry and Biochemistry, the University of Texas at Austin, Austin,
Texas 78712. E-mail: [email protected].
Brent and Sheila Iverson
Austin, Texas
January, 2013
Vv
© 2014 Cengagge Learning. ; All Rights Reserved. May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part.
Digitized by the Internet Archive
in 2022 with funding from
Kahle/Austin Foundation
https://archive.org/details/studentstudyguid0000brow
CONTENTS:
1
Covalent Bonding and Shapes of Molecules 1
74
Alkanes and Cycloalkanes 32
3
Stereoisomerism and Chirality 60
4
Acids and Bases 777
5
Alkenes: Bonding, Nomenclature, and Properties 102
6
Reactions of Alkenes 115
7 Alkynes 150
8
Haloalkanes, Halogenation, and Radical Reactions 171
9
Nucleophilic Substitution and 8-Elimination 190
10
Alcohols 224
11 Ethers, Epoxides and Sulfides 261
12 Infrared Spectroscopy 293
13
Nuclear Magnetic Resonance Spectroscopy 300
14 Mass Spectrometry 317
15 An Introduction to Organometallic Compounds 330
16 Aldehydes and Ketones 344
hey, Carboxylic Acids 402
18 Functional Derivatives of Carboxylic Acids 429
19 Enolate Anions and Enamines 476
20 Dienes, Conjugated Systems, and Pericyclic Reactions 545
21 Benzene and the Concept of Aromaticity 573
ne Reactions of Benzene and its Derivatives 633
8 Amines 685
24 Catalytic Carbon-Carbon Bond Formation 736
25 Carbohydrates 779
26 Lipids 797
2, Amino Acids and Proteins 812
28 Nucleic Acids 831
29 Organic Polymer Chemistry 841
Vil
© 2014 Cengage Learning. All Rights Reserved. May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part.
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