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This innovative organic chemistry textbook from acclaimed educator Paula Bruice is organized in a way that discourages rote memorization. The author's writing has been praised for anticipating readers' questions, and appeals to their need to learn visually and by solving problems. Emphasizing that learners should reason their way to solutions rather than memorize facts, Bruice encourages them to think about what they have learned previously and apply that knowledge in a new setting.

Table of contents

Ch. 1	Electronic Structure and Bonding, Acids and Bases	1
Ch. 2	An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure	51
Ch. 3	Reactions of Alkenes. Thermodynamics and Kinetics	105
Ch. 4	Stereochemistry: The Arrangement of Atoms in Space; The Stereochemistry of Addition Reactions	178
Ch. 5	Reactions of Alkynes	242
Ch. 6	Electron Delocalization, Resonance, and Aromaticity	268
Ch. 7	Reactions of Dienes	310
Ch. 8	Reactions of Alkanes: Radicals	341
Ch. 9	Substitution and Elimination Reactions at an sp[superscript 3]-Hybridized Carbon I: The Halogen Leaving Group	368
Ch. 10	Substitution and Elimination Reactions at an sp[superscript 3]-Hybridized Carbon II: Leaving Groups Other Than Halogen. Organometallic Compounds	437
Ch. 11	Oxidation-Reduction Reactions	483
Ch. 12	Identification of Organic Compounds by Mass Spectrometry and Infrared Spectroscopy	521
Ch. 13	Reactions of Benzene and Substituted Benzenes	564
Ch. 14	Identification of Organic Compounds by NMR Spectroscopy and Ultraviolet/Visible Spectroscopy	633
Ch. 15	Carbonyl Compounds I: Reactions of Carboxylic Acids and Their Derivatives with Oxygen and Nitrogen Nucleophiles	706
Ch. 16	Carbonyl Compounds II: Reactions of Carbonyl Compounds with Carbon and Hydrogen Nucleophiles. Reactions of Aldehydes and Ketones with Oxygen and Nitrogen Nucleophiles. Reactions of [alpha],[beta]-Unsaturated Carbonyl Compounds	763
Ch. 17	Carbonyl Compounds III: Reactions at the [alpha]-Carbon	816
Ch. 18	Carbohydrates	870
Ch. 19	Heterocyclic Compounds	911
Ch. 20	Pericyclic Reactions	949
Ch. 21	Multistep Organic Synthesis	979
Ch. 22	Synthetic Polymers	1011
Ch. 23	Amino Acids, Peptides, and Proteins	1043
Ch. 24	Catalysis	1089
Ch. 25	The Organic Mechanisms of the Coenzymes	1125
Ch. 26	Lipids	1168
Ch. 27	Nucleosides, Nucleotides, and Nucleic Acids	1199
Ch. 28	The Organic Chemistry of Drugs: Discovery and Design	1244
	App. I Physical Properties of Organic Compounds	A
	App. II pK[subscript a] Values	A-7
	App. III Derivations of Rate Laws	A-9
	App. IV Summary of Methods Used to Synthesize a Particular Functional Group	A-12
	App. V Spectroscopy Tables	A-16
	App. VI The Glycolytic Cycle and the Krebs Cycle	A-22
	Answers to Selected Problems	A-24
	Glossary	G-1
	Index	I-1