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Ch1 - C ONTENTS 1 2 The material in this volume was...

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5 10 15 20 25 This Student Study Guide is a companion to the fifth edition of Organic Chemistry by William Brown, Chlistopher Foote, Brent Iverson, and Eric Anslyn. 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-dllnensional and understanding the three-dimenSionalAy 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. . The material in this volume was reviewed for accuracy by Brent and Sheila Iverson. If y~u 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 February, 2008 CONTENTS: 1 Covalent Bonding and Shapes of Molecules 1 2 Alkanes and Cycloalkanes 32 3 Stereoisomerism and Chirality 59 4 Acids and Bases 75 Alkenes: Bonding, Nomenclature, and Properties 99 6' Reactions of Alkenes 112 7 Alkynes 145 8 Haloalkanes, Halogenation, and Radical Reactions 163 9 Nucleophilic Substitution and II-Elimination 179 11 Ethers, Epoxides and Sulfides Alcohols 210 243 12 Infrared Spectroscopy 273 13 Nuclear Magnetic Resonance Spectroscopy 280 14 Mass Spectrometry 297 Organometallic Compounds 310 16· Aldehydes and Ketones 321 17 Carboxylic Acids 374 18 Functional Derivatives of Carboxylic Acids 397 19 Enolate Anions and Enamines 440 .Conjugated Systems 503 ' 22 Reactions of Benzene and its Derivatiyes 567' 24 Carbon-Carbon Bond Formation and Synthesis 662' 21 Benzene and the Concept of Aromaticity 511 23 Amines 616 26 Lipids Carbohydrates 715 733 27 Amino Acids and Proteins 747 28 Nucleic Acids 766 29 Organic Polymer Chemistry 776
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Chapter I: Covalent Bonding and Shapes of Molecules Solutions CHAPTER 1 Solutions to the Proble'ms .PrQblem 1.1 Write and cQmpare the ground-state electron cQnfiguratiQns for each pair Qf elements: (a) CarbQn and silicQn C (6 electrons) Is 2 ZS 2 Zp2 8i (14 electrons) IS2Zs2Zp63s23p'2 . . Both carbon and silicon have four electrons in their outermost (valence) shells. (b) Oxygen and sulfur o (8 electrons) Is 2 'Zs 2 Zp4 8 (16 electrons) Is2Zs2Zp63s23p4 Both oxygen and sulfur have six electrons in their outermost (valence) shells.
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