, Study Guide and Solutions Manual
Organic Chemistry
A Short Course
THIRTEENTH EDITION
David J. Hart
The Ohio State University
Christopher M. Hadad
The Ohio State University
Leslie E. Craine
Central Connecticut State University
Harold Hart
Michigan State University
Prepared by
David J. Hart
The Ohio State University
Christopher M. Hadad
The Ohio State University
Leslie E. Craine
Central Connecticut State University
Harold Hart
Michigan State University
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Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part.
,Contents
Introduction to the Student .................................................................................................... v
Chapter 1 Bonding and Isomerism ................................................................................. 1
Chapter 2 Alkanes and Cycloalkanes; Conformational and Geometric Isomerism ...... 19
Chapter 3 Alkenes and Alkynes ................................................................................... 37
Chapter 4 Aromatic Compounds .................................................................................. 61
Chapter 5 Stereoisomerism .......................................................................................... 87
Chapter 6 Organic Halogen Compounds; Substitution and Elimination Reactions .... 109
Chapter 7 Alcohols, Phenols, and Thiols ................................................................... 123
Chapter 8 Ethers and Epoxides ................................................................................. 141
Chapter 9 Aldehydes and Ketones ............................................................................. 157
Chapter 10 Carboxylic Acids and Their Derivatives ..................................................... 187
Chapter 11 Amines and Related Nitrogen Compounds ............................................... 211
Chapter 12 Spectroscopy and Structure Determination ............................................... 233
Chapter 13 Heterocyclic Compounds ........................................................................... 247
Chapter 14 Synthetic Polymers .................................................................................... 263
Chapter 15 Lipids and Detergents ................................................................................ 279
Chapter 16 Carbohydrates ........................................................................................... 291
Chapter 17 Amino Acids, Peptides, and Proteins ........................................................ 317
Chapter 18 Nucleotides and Nucleic Acids .................................................................. 345
Summary of Synthetic Methods ........................................................................................ 361
Summary of Reaction Mechanisms .................................................................................. 375
Review Problems On Synthesis ......................................................................................... 381
Sample Multiple Choice Test Questions ........................................................................... 385
© 2012 Cengage Learning. All Rights Reserved. May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part.
iii
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part.
, Introduction to the Student
This study guide and solutions book was written to help you learn organic chemistry. The
principles and facts of this subject are not easily learned by simply reading them, even
repeatedly. Formulas, equations, and molecular structures are best mastered by written
practice. To help you become thoroughly familiar with the material, we have included many
problems within and at the end of each chapter in the text.
It is our experience that such questions are not put to their best use unless correct
answers are also available. Indeed, answers alone are not enough. If you know how to work
a problem and find that your answer agrees with the correct one, fine. But what if you work
conscientiously, yet cannot solve the problem? You then give in to temptation, look up the
answer, and encounter yet another dilemma–how in the world did the author get that
answer? This solutions book has been written with this difficulty in mind. For many of the
problems, all of the reasoning involved in getting the correct answer is spelled out in detail.
Many of the answers also include cross-references to the text. If you cannot solve a
particular problem, these references will guide you to parts of the text that you should
review.
Each chapter of the text is briefly summarized. Whenever pertinent, the chapter
summary is followed by a list of all the new reactions and mechanisms encountered in that
chapter. These lists should be especially helpful to you as you review for examinations.
When you study a new subject, it is always useful to know what is expected. To help
you, we have included in this study guide a list of learning objectives for each chapter—that
is, a list of what you should be able to do after you have read and studied that chapter. Your
instructor may want to delete items from these lists of objectives or add to them. However,
we believe that if you have mastered these objectives—and the problems should help you to
do this—you should have no difficulty with examinations. Furthermore, you should be very
well prepared for further courses that require this course as a prerequisite.
Near the end of this study guide you will find additional sections that may help you to
study for the final examination in the course. The SUMMARY OF SYNTHETIC METHODS
lists the important ways to synthesize each class of compounds discussed in the text. It is
followed by the SUMMARY OF REACTION MECHANISMS. Both of these sections have
references to appropriate portions of the text, in case you feel that further review is
necessary. Finally, you will find two lists of sample test questions. The first deals with
synthesis, and the second is a list of multiple-choice questions. Both of these sets should
help you prepare for examinations.
In addition, we offer you a brief word of advice about how to learn the many
reactions you will study during this course. First, learn the nomenclature systems thoroughly
for each new class of compounds that is introduced. Then, rather than memorizing the
particular examples of reactions given in the text, study reactions as being typical of a class
of compounds. For example, if you are asked how compound A will react with compound B,
proceed in the following way. First ask yourself: to what class of compounds does A belong?
How does this class of compounds react with B (or with compounds of the general class to
which B belongs)? Then proceed from the general reaction to the specific case at hand. This
approach will probably help you to eliminate some of the memory work often associated with
organic chemistry courses. We urge you to study regularly, and hope that this study guide
and solutions book will make it easier for you to do so.
© 2012 Cengage Learning. All Rights Reserved. May not be scanned, copied or duplicated, or posted to a publicly accessible website, in whole or in part.
v
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part.
