Organic Chemistry (with InfoTrac and CD-ROM)

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  • Edition: 5th
  • Format: Hardcover
  • Copyright: 1999-08-25
  • Publisher: Brooks Cole
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Supplemental Materials

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  • The New copy of this book will include any supplemental materials advertised. Please check the title of the book to determine if it should include any access cards, study guides, lab manuals, CDs, etc.


John McMurry's international best-seller is widely and consistently praised as the most clearly written book on the market. Why? In John McMurry's words: "I have been asked hundreds of times over the past ten years why I wrote this book. I wrote this book because I love writing. I get great pleasure and satisfaction from taking a complicated subject, turning it around until I see it clearly from a new angle, and then explaining it in simple words. I write to explain chemistry to students the way I wish it had been explained to me years ago." Through his lucid writing and ability to show the beauty and logic of organic chemistry, McMurry makes learning enjoyable for students. The highest compliment that can be given to a chemistry book applies to McMurry: It works! Mainstream in level, McMurry's coverage is concise yet doesn't omit any key topics. McMurry blends the traditional functional-group approach with a mechanistic approach. The primary approach, by functional group, begins with the simple and progresses to the more complex so that readers who are not yet versed in the subtleties of mechanisms are first exposed to the "what" of chemistry before beginning to grapple with the "why." Within this primary organization, the author places a heavy emphasis on explaining the fundamental mechanistic similarities. In this edition, McMurry retains his standard-setting features (including his innovative vertical format for explaining reaction mechanisms) while revising his text line-by-line to include hundreds of small but important improvements. For example, the Sixth Edition includes new examples, additional steps in existing examples, new problems, new phrases to clarify the exposition, and a vibrant new art program. In addition, new icons in the text lead students to a variety of new online resources. McMurry's text is in use at hundreds of colleges and universities around the world, from North America, to the United Kingdom and the Pacific Rim.

Table of Contents

Solutions to Problems
Structure and Bondingp. 1
Polar Bonds and Their Consequencesp. 17
Review Unit 1p. 35
Organic Compounds: Alkanes and Cycloalkanesp. 38
Stereochemistry of Alkanes and Cycloalkanesp. 59
An Overview of Organic Reactionsp. 84
Review Unit 2p. 100
Alkenes: Structure and Reactivityp. 104
Alkenes: Reactions and Synthesisp. 126
Alkynes: An Introduction to Organic Synthesisp. 151
Review Unit 3p. 173
Stereochemistryp. 176
Alkyl Halidesp. 205
Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminationsp. 224
Review Unit 4p. 254
Structure Determination: Mass Spectrometry and Infrared Spectroscopyp. 258
Structure Determination: Nuclear Magnetic Resonance Spectroscopyp. 278
Review Unit 5p. 302
Conjugated Dienes and Ultraviolet Spectroscopyp. 305
Benzene and Aromaticityp. 327
Chemistry of Benzene: Electrophilic Aromatic Substitutionp. 345
Review Unit 6p. 381
Alcohols and Phenolsp. 385
Ethers and Epoxides; Thiols and Sulfidesp. 416
Review Unit 7p. 442
Aldehydes and Ketones: Nucleophilic Addition Reactionsp. 445
Carboxylic Acidsp. 484
Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactionsp. 506
Review Unit 8p. 541
Carbonyl Alpha-Substitution Reactionsp. 545
Carbonyl Condensation Reactionsp. 570
Aminesp. 601
Review Unit 9p. 635
Biomolecules: Carbohydratesp. 638
Biomolecules: Amino Acids, Peptides, and Proteinsp. 663
Review Unit 10p. 690
Biomolecules: Lipidsp. 693
Biomolecules: Heterocycles and Nucleic Acidsp. 713
The Organic Chemistry of Metabolic Pathwaysp. 739
Review Unit 11p. 761
Orbitals and Organic Chemistry: Pericyclic Reactionsp. 765
Synthetic Polymersp. 786
Review Unit 12p. 802
Functional-Group Synthesisp. 805
Functional-Group Reactionsp. 810
Reagents in Organic Chemistryp. 814
Name Reactions in Organic Chemistryp. 821
Abbreviationsp. 829
Infrared Absorption Frequenciesp. 832
Proton NMR Chemical Shiftsp. 835
Top 40 Organic Chemicalsp. 836
Nobel Prize Winners in Chemistryp. 838
Answers to Review-Unit Questionsp. 846
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