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Introduction to Organic Chemistry, 4th Edition

January 2010, ©2011
Introduction to Organic Chemistry, 4th Edition (EHEP001574) cover image
This text provides an introduction to organic chemistry for students who require the fundamentals of organic chemistry as a requirement for their major. It is most suited for a one semester organic chemistry course. In an attempt to highlight the relevance of the material to students, the authors place a strong emphasis on showing the interrelationship between organic chemistry and other areas of science, particularly the biological and health sciences. The text illustrates the use of organic chemistry as a tool in these sciences; it also stresses the organic compounds, both natural and synthetic, that surround us in everyday life: in pharmaceuticals, plastics, fibers, agrochemicals, surface coatings, toiletry preparations and cosmetics, food additives, adhesives, and elastomers.
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1 Covalent Bonding and Shapes of Molecules.

1.1 How Do We Describe the Electronic Structure of Atoms?

1.2 What Is the Lewis Model of Bonding?

1.3 How Do We Predict Bond Angles and the Shapes of Molecules?

1.4 How Do We Predict If a Molecule Is Polar or Nonpolar?

1.5 What Is Resonance?

1.6 What Is the Molecular Orbital Model of Covalent Bonding?

1.7 What Are Functional Groups?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Problems.

CHEMICAL CONNECTIONS.

1A Buckyball: A New Form of Carbon.

2 Acids and Bases.

2.1 What Are Arrhenius Acids and Bases?

2.2 What Are Brønsted–Lowry Acids and Bases?

2.3 How Do We Measure the Strength of an Acid or Base?

2.4 How Do We Determine the Position of Equilibrium in an Acid–Base Reaction?

2.5 What Are the Relationships between Acidity and Molecular Structure?

2.6 What Are Lewis Acids and Bases?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

3 Alkanes and Cycloalkanes.

3.1 What Are Alkanes?

3.2 What Is Constitutional Isomerism in Alkanes?

3.3 How Do We Name Alkanes?

3.4 What Are Cycloalkanes?

3.5 What Is the IUPAC System of Nomenclature?

3.6 What Are the Conformations of Alkanes and Cycloalkanes?

3.7 What Is Cis–Trans Isomerism in Cycloalkanes?

3.8 What Are the Physical Properties of Alkanes and Cycloalkanes?

3.9 What Are the Characteristic Reactions of Alkanes?

3.10 What Are the Sources of Alkanes?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

Putting It Together.

CHEMICAL CONNECTIONS.

3A The Poisonous Puffer Fish.

3B Octane Rating: What Those Numbers at the Pump Mean.

4 Alkenes and Alkynes.

4.1 What Are the Structures and Shapes of Alkenes and Alkynes?

4.2 How Do We Name Alkenes and Alkynes?

4.3 What Are the Physical Properties of Alkenes and Alkynes?

4.4 What Are Terpenes?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Problems.

CHEMICAL CONNECTIONS.

4A Ethylene, a Plant Growth Regulator.

4B Why Plants Emit Isoprene.

5 Reactions of Alkenes and Alkynes.

5.1 What Are the Characteristic Reactions of Alkenes?

5.2 What Is a Reaction Mechanism?

5.3 What Are the Mechanisms of Electrophilic Additions to Alkenes?

5.4 What Are Carbocation Rearrangements?

5.5 What Is Hydroboration–Oxidation of an Alkene?

5.6 What Is Ozonolysis of an Alkene?

5.7 How Can an Alkene Be Reduced to an Alkane?

5.8 Why Are 1-Alkynes (Terminal Alkynes) Weak Acids?

5.9 How Can an Acetylide Anion Be Used to Create a New Carbon–Carbon Bond?

5.10 What Is the Product of the Acid-Catalyzed Hydration of Alkyne?

5.11 How Can Alkynes Be Reduced to Alkenes and Alkanes?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

CHEMICAL CONNECTIONS.

5A Cis–Trans Isomerism in Vision.

6 Chirality: The Handedness of Molecules.

6.1 What Are Stereoisomers?

6.2 What Are Enantiomers?

6.3 How Do We Designate the Configuration of a Stereocenter?

6.4 What Is the 2n Rule?

6.5 How Do We Describe the Chirality of Cyclic Molecules with Two or More Stereocenters?

6.6 How Do We Describe the Chirality of Molecules with Three or More Stereocenters?

6.7 What Are the Properties of Stereoisomers?

6.8 How Is Chirality Detected in the Laboratory?

6.9 What Is the Significance of Chirality in the Biological World?

6.10 How Can Enantiomers Be Resolved?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Problems.

Putting It Together.

CHEMICAL CONNECTIONS.

6A Chiral Drugs.

7 Haloalkanes.

7.1 How Are Haloalkanes Named?

7.2 What Are the Characteristic Reactions of Haloalkanes?

7.3 What Are the Products of Nucleophilic Aliphatic Substitution Reactions?

7.4 What Are the SN2 and SN1 Mechanisms for Nucleophilic Substitution?

7.5 What Determines Whether SN1 or SN2 Predominates?

7.6 How Can SN1 and SN2 Be Predicted Based on Experimental Conditions?

7.7 What Are the Products of ß-Eliminations?

7.8 What Are the E1 and E2 Mechanisms for ß-Elimination?

7.9 How Do Nucleophilic Substitution and b-Elimination Compete?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

CHEMICAL CONNECTIONS.

7A The Environmental Impact of Chlorofluorocarbons.

7B The Effect of Chlorofluorocarbon Legislation on Asthma Sufferers.

8 Alcohols, Ethers, and Thiols.

8.1 What Are Alcohols?

8.2 What Are the Characteristic Reactions of Alcohols?

8.3 What Are Ethers?

8.4 What Are Epoxides?

8.5 What Are Thiols?

8.6 What Are the Characteristic Reactions of Thiols?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

CHEMICAL CONNECTIONS.

8A Nitroglycerin: An Explosive and a Drug.

8B Blood Alcohol Screening.

8C Ethylene Oxide: A Chemical Sterilant.

9 Benzene and Its Derivatives.

9.1 What Is the Structure of Benzene?

9.2 What Is Aromaticity?

9.3 How Are Benzene Compounds Named, and What Are Their Physical Properties?

9.4 What Is the Benzylic Position, and How Does It Contribute to Benzene Reactivity?

9.5 What Is Electrophilic Aromatic Substitution?

9.6 What Is the Mechanism of Electrophilic Aromatic Substitution?

9.7 How Do Existing Substituents on Benzene Affect Electrophilic Aromatic Substitution?

9.8 What Are Phenols?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

CHEMICAL CONNECTIONS.

9A Carcinogenic Polynuclear Aromatics and Cancer.

9B Capsaicin, for Those Who Like It Hot.

10 Amines.

10.1 What Are Amines?

10.2 How Are Amines Named?

10.3 What Are the Characteristic Physical Properties of Amines?

10.4 What Are the Acid–Base Properties of Amines?

10.5 What Are the Reactions of Amines with Acids?

10.6 How Are Arylamines Synthesized?

10.7 How Are Primary Aromatic Amines Used in Synthesis?

10.8 How Do Amines Act as Nucleophiles?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

Putting It Together.

CHEMICAL CONNECTIONS.

10A Morphine as a Clue in the Design and Discovery of Drugs.

10B The Poison Dart Frogs of South America: Lethal Amines.

11 Infrared Spectroscopy.

11.1 What Is Electromagnetic Radiation?

11.2 What Is Molecular Spectroscopy?

11.3 What Is Infrared Spectroscopy?

11.4 How Do We Interpret Infrared Spectra?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Problems.

CHEMICAL CONNECTIONS.

11A Infrared Spectroscopy: A Window on Brain Activity.

12 Nuclear Magnetic Resonance Spectroscopy.

12.1 What Are the Magnetic Properties of Nuclei?

12.2 What Is Nuclear Magnetic Resonance?

12.3 What Is Shielding?

12.4 How Is an NMR Spectrum.

Obtained?

12.5 How Many Resonance Signals Will a Compound Yield in Its NMR Spectrum?

12.6 What Is Signal Integration?

12.7 What Is Chemical Shift?

12.8 What Is Signal Splitting?

12.9 What Is 13C-NMR Spectroscopy, and How Does It Differ from 1H-NMR Spectroscopy?

12.10 How Do We Interpret NMR Spectra?

12.11 How Do We Solve an NMR Problem?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Problems.

CHEMICAL CONNECTIONS.

12A Magnetic Resonance Imaging.

13 Aldehydes and Ketones.

13.1 What Are Aldehydes and Ketones?

13.2 How Are Aldehydes and Ketones Named?

13.3 What Are the Physical Properties of Aldehydes and Ketones?

13.4 What Is the Most Common Reaction Theme of Aldehydes and Ketones?

13.5 What Are Grignard Reagents, and How Do They React with Aldehydes and Ketones?

13.6 What Are Hemiacetals and Acetals?

13.7 How Do Aldehydes and Ketones React with Ammonia and Amines?

13.8 What Is Keto–Enol Tautomerism?

13.9 How Are Aldehydes and Ketones Oxidized?

13.10 How Are Aldehydes and Ketones Reduced?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

CHEMICAL CONNECTIONS.

13A A Green Synthesis of Adipic Acid.

14 Carboxylic Acids.

14.1 What Are Carboxylic Acids?

14.2 How Are Carboxylic Acids Named?

14.3 What Are the Physical Properties of Carboxylic Acids?

14.4 What Are the Acid–Base Properties of Carboxylic Acids?

14.5 How Are Carboxyl Groups Reduced?

14.6 What Is Fischer Esterification?

14.7 What Are Acid Chlorides?

14.8 What Is Decarboxylation?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

CHEMICAL CONNECTIONS.

14A From Willow Bark to Aspirin and Beyond.

14B Esters as Flavoring Agents.

14C Ketone Bodies and Diabetes.

15 Functional Derivatives of Carboxylic Acids.

15.1 What Are Some Derivatives of Carboxylic Acids, and How Are They Named?

15.2 What Are the Characteristic Reactions of Carboxylic Acid Derivatives?

15.3 What Is Hydrolysis?

15.4 How Do Carboxylic Acid Derivatives React with Alcohols?

15.5 How Do Carboxylic Acid Derivatives React with Ammonia and Amines?

15.6 How Can Functional Derivatives of Carboxylic Acids Be Interconverted?

15.7 How Do Esters React with Grignard Reagents?

15.8 How Are Derivatives of Carboxylic Acids Reduced?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

Putting It Together.

CHEMICAL CONNECTIONS.

15A Ultraviolet Sunscreens and Sunblocks.

15B From Moldy Clover to a Blood Thinner.

15C The Penicillins and Cephalosporins: ß-Lactam Antibiotics.

15D The Pyrethrins: Natural Insecticides of Plant Origin.

15E Systematic Acquired Resistance in Plants.

16 Enolate Anions.

16.1 What Are Enolate Anions, and How Are They Formed?

16.2 What Is the Aldol Reaction?

16.3 What Are the Claisen and Dieckmann Condensations?

16.4 How Are Aldol Reactions and Claisen Condensations Involved in Biological Processes?

16.5 What Is the Michael Reaction?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

CHEMICAL CONNECTIONS.

16A Drugs That Lower Plasma Levels of Cholesterol.

16B Antitumor Compounds:The Michael Reaction in Nature.

17 Organic Polymer Chemistry.

17.1 What Is the Architecture of Polymers?

17.2 How Do We Name and Show the Structure of a Polymer?

17.3 What Is Polymer Morphology? Crystalline versus Amorphous Materials.

17.4 What Is Step-Growth Polymerization?

17.5 What Are Chain-Growth Polymers?

17.6 What Plastics Are Currently Recycled in Large Quantities?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

CHEMICAL CONNECTIONS.

17A Stitches That Dissolve.

17B Paper or Plastic?

18 Carbohydrates.

18.1 What Are Carbohydrates?

18.2 What Are Monosaccharides?

18.3 What Are the Cyclic Structures of Monosaccharides?

18.4 What Are the Characteristic Reactions of Monosaccharides?

18.5 How Is the Concentration of Blood Glucose Determined?

18.6 What Is L-Ascorbic Acid (Vitamin C)?

18.7 What Are Disaccharides and Oligosaccharides?

18.8 What Are Polysaccharides?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

Putting It Together.

CHEMICAL CONNECTIONS.

18A Relative Sweetness of Carbohydrate and Artificial Sweeteners.

18B A, B,AB, and O Blood-Group Substances.

19 Amino Acids and Proteins.

19.1 What Are the Many Functions of Proteins?

19.2 What Are Amino Acids?

19.3 What Are the Acid–Base Properties of Amino Acids?

19.4 What Are Polypeptides and Proteins?

19.5 What Is the Primary Structure of a Polypeptide or Protein?

19.6 What Are the Three-Dimensional Shapes of Polypeptides and Proteins?

19.7 What Is Denaturation?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

CHEMICAL CONNECTIONS.

19A Spider Silk: A Chemical and Engineering Wonder of Nature.

20 Nucleic Acids.

20.1 What Are Nucleosides and Nucleotides?

20.2 What Is the Structure of DNA?

20.3 What Are Ribonucleic Acids (RNA)?

20.4 What Is the Genetic Code?

20.5 How Is DNA Sequenced?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Problems.

CHEMICAL CONNECTIONS.

20A The Search for Antiviral Drugs.

20B DNA Fingerprinting.

21 Lipids.

21.1 What Are Triglycerides?

21.2 What Are Soaps and Detergents?

21.3 What Are Phospholipids?

21.4 What Are Steroids?

21.5 What Are Prostaglandins?

21.6 What Are Fat-Soluble Vitamins?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Problems.

CHEMICAL CONNECTIONS.

21A Snake Venom Phospholipases.

21B Nonsteroidal Estrogen Antagonists.

22 The Organic Chemistry of Metabolism.

22.1 What Are the Key Participants in Glycolysis, ß-Oxidation of Fatty Acids, and the Citric Acid Cycle?

22.2 What Is Glycolysis?

22.3 What Are the Ten Reactions of Glycolysis?

22.4 What Are the Fates of Pyruvate?

22.5 What Are the Reactions of the ß-Oxidation of Fatty Acids?

22.6 What Are the Reactions of the Citric Acid Cycle?

Key Terms and Concepts.

Summary of Key Questions.

Quick Quiz.

Key Reactions.

Problems.

APPENDIX 1 Acid Ionization Constants for the Major Classes of Organic Acids.

APPENDIX 2 Characteristic 1H-NMR Chemical Shifts.

APPENDIX 3 Characteristic 13C-NMR Chemical Shifts.

APPENDIX 4 Characteristic Infrared Absorption Frequencies.

Glossary.

Answers Section.

Index.

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William H. Brown is Professor Emeritus at Beloit College, where he was twice named Teacher of the Year. He is also the author of two other college textbooks: Organic Chemistry 5/e, coauthored with Chris Foote, Brent Iverson, and Eric Anslyn, published in 2009, and General, Organic, and Biochemistry 9/e, coauthored with Fred Bettelheim, Mary Campbell, and Shawn Farrell, published in 2010. He received his Ph.D. from Columbia University under the direction of Gilbert Stork and did postdoctoral work at California Institute of Technology and the University of Arizona. Twice he was Director of a Beloit College World Affairs Center seminar at the University of Glasgow, Scotland. In 1999, he retired from Beloit College to devote more time to writing and development of educational materials. Although officially retired, he continues to teach Special Topics in Organic Synthesis on a yearly basis. Bill and his wife Carolyn enjoy hiking in the canyon country of the Southwest. In addition, they both enjoy quilting and quilts.

Thomas Poon is Associate Professor of Chemistry in the Joint Science Department of Claremont McKenna, Pitzer, and Scripps Colleges, three of the five undergraduate institutions that make up the Claremont Colleges in Claremont, California. He received his B.S. degree from Fairfield University (CT) and his Ph.D. from the University of California, Los Angeles under the direction of Christopher S. Foote. Poon was a Camille and Henry Dreyfus Postdoctoral Fellow under Bradford P. Mundy at Colby College (ME) before joining the faculty at Randolph-Macon College (VA) where he received the Thomas Branch Award for Excellence in Teaching in 1999. He was a visiting scholar at Columbia University (NY) in 2002 (and again in 2004) where he worked on projects in both research and education with his friend and mentor, Nicholas J. Turro. He has taught organic chemistry, forensic chemistry, upper-level courses in advanced laboratory techniques, and a first-year seminar class titled Science of Identity. His favorite activity is working alongside undergraduates in the laboratory on research problems involving the investigation of synthetic methodology in zeolites, zeolite photochemistry, natural products isolation, and reactions of singlet oxygen. When not in the lab, he likes to play guitar and sing funny chemistry songs to his daughter Sophie.

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  • “How To” boxes have been added within the chapters, providing students with techniques and hints for approaching and understanding key course topics. i.e. “How to Draw Chair Conformations”, “How to determine Which Acid is Stronger or Weaker”.

  • Cumulative review questions, entitled “Putting It Together”, appear after groups of selected chapters. Because organic chemistry is, by nature, a cumulative subject, it is important for students to encounter problems that not only test them on the current chapter’s material, but also on the material from previous chapters.  These questions will provide students with an opportunity to test their understanding of multiple concepts and ideas and help them prepare for tests and exams. As one text reviewer noted, “Tools for assessment are very important to avoid illusions during the semester.  Students have to know where they stand and when they have to make an effort.  Most of them have difficulties to come from behind when they have failed to understand several chapters.  I would definitely assign these to my students”.

  • Every Example consists of three steps – the problem statement, a strategy, and the solution. New to this edition, the Authors have added the second step entitled “Strategy”. The purpose of this step is to provide further guidance to students as they attempt to solve the problem. In essence, the Strategy step will help students to answer the question, “Where do I begin to solve this problem?” 
    • Each example concludes with a reference to an end of chapter problem(s) that practices the same concept or technique so that students have an opportunity to practice, reinforce and confirm their understanding of the concept/technique.
    • When students are working end of chapter exercises, a selection of these will include a visual reference to an in-text worked example that they can reference for assistance in completing the exercise.
    • More in-text examples have been added that focus on everyday life and serve to reinforce and illustrate key concepts. 

  • “Quick Quizzes” have been added to the end of each chapter, allowing students to promptly assess their grasp of the material within each chapter.  The answers to the Quick Quiz sections can be found within the text Answer Appendix.

  • An earlier introduction of biochemistry: the biological molecules chapters (Proteins and Nucleic Acids) have been streamlined.  These chapters traditionally fall at the end of most textbooks, as well as at the end of the semester, and it is often difficult to find time to cover these important biochemistry concepts within one semester.  However, these chapters contain some of the most relevant material for health-related and biological science majors and it is important to emphasize that organic chemistry is relevant to their studies.   In this edition of the text, more biochemistry examples appear in the earlier chapters, which now contain material from the Proteins and Nucleic Acids chapters of the text.  Students will be exposed to important biological molecules earlier in the course, which helps to reinforce the importance of biochemistry to organic chemistry.

  • The number of end of chapter exercises has increased by 15%, providing students with more problems for practice.

  • More Chemical Connections boxes have been added to this edition. These boxes focus on the applications of organic chemistry to everyday life. 
    • Assessment questions have been added to the Chemical Connections boxes which connect back to the concepts covered within the chapter, and give students additional opportunities to practice their understanding. Instructors could assign these and/ or discuss them in class. Answers to these are found in the Student Solutions Manual.

  • Dialog bubbles have been added to the text figures/illustrations, where appropriate, to provide students with detailed information about what is taking place within the illustration.  Many students are visual learners, and these dialog bubbles provide visual cues for students in reaction schemes, tables, and figures.  Reviewers responded well to this new feature, stating:
    •   “It gets their attention much better than information in a paragraph.  It is highly visual, and that should appeal to a large section of the student population.”
    • “Anything that will highlight or draw attention to the important parts of a reaction is helpful for the students.  Because these students are new to organic chemistry, they need all of the visual clues possible to show them what is important in each reaction.”

  • The traditional end-of-chapter summary has been replaced by a list of Key Terms, accompanied by a “Summary of Key Questions”, which summarizes the main points of each chapter section in a concise fashion. 

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  • An emphasis on the mechanistic understanding of reactions, rather than memorization.

  •   “Chemical Connections” boxes illustrate the applications of organic chemistry.

  • Examples integrated throughout the text highlight the application of organic chemistry to the health and biological sciences, and, more broadly, to the everyday world.

  • Extensive use of worked examples to illustrate important concepts.

  • Categorized end of chapter problems with varied levels of difficulty to challenge students.

  •   Text is easy to read and at the appropriate level and style for the intended student audience.

  • High impact, four-color art program.  Photos, conceived and developed specifically for this text, show organic chemistry as it occurs in the laboratory and in everyday life.

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Wiley is pleased to offer Sapling Learning with our Chemistry titles. Sapling Learning offers interactive homework and instruction designed to improve student performance and outcomes. Its software is designed to offer students highly targeted instructional feedback and coaching, and includes rich tutorial questions. With Sapling Learning instructors can author and edit their own question content. Sapling Learning is known for its strong customer service (Ph.D. Chemists on staff) who also work with instructors to create and customize problem content. Sapling Learning is completely textbook independent and does not contain an eBook.
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Students Resources
Wiley Student Companion Site
Sapling
Wiley is pleased to offer Sapling Learning with our Chemistry titles. Sapling Learning offers interactive homework and instruction designed to improve student performance and outcomes. Its software is designed to offer students highly targeted instructional feedback and coaching, and includes rich tutorial questions. With Sapling Learning instructors can author and edit their own question content. Sapling Learning is known for its strong customer service (Ph.D. Chemists on staff) who also work with instructors to create and customize problem content. Sapling Learning is completely textbook independent and does not contain an eBook.
Available Materials
by William H. Brown, Thomas Poon
978-0-470-55494-4
March 2010, ©2011, Paperback (E-book also available)
Authored by Felix Lee, of the University of Western Ontario: contains detailed solutions to all text problems.
by T. W. Graham Solomons
978-0-471-36271-5
August 1999, ©2000, Display stands, trays etc
Created by Darling Models, an affordable modeling kit that can be packaged with the text for added value to the student.
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Introduction to Organic Chemistry, 4th Edition
ISBN : 978-0-470-56936-8
July 2010, ©2011
$93.50   BUY

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Introduction to Organic Chemistry, 4th Edition Binder Ready Version
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Introduction to Organic Chemistry, 4th Edition
ISBN : 978-0-470-12923-4
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Introduction to Organic Chemistry, Textbook and Student Solutions Manual , 4th Edition
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