Organic Chemistry

by Sorrell, Thomas N.

• ISBN13: 9781891389382
• ISBN10: 1891389386
• Edition: 2nd
• Format: Hardcover
• Copyright: 2005-12-20
• Publisher: Univ Science Books

Table of Contents

Preface	xvii
To the Student	xix
To the Instructor	xxi
Acknowledgments	xxiii
The Structures of Organic Molecules	1	(34)
Structural Components of Organic Molecules	2	(1)
Structural Formulas and Condensed Structures	3	(6)
Systematic Nomenclature: Iupac Names	9	(9)
Constitutional Isomers and Hydrocarbon Substituents	18	(7)
Naming Organic Compounds	25	(10)
Chapter Summary	29	(6)
Bonding in Organic Molecules	35	(42)
Lewis Structures	35	(5)
Bond Properties	40	(3)
Resonance Structures	43	(6)
The Formation of Bonds	49	(2)
Hybrid Orbitals and Shapes of Molecules	51	(9)
Bonus With Herteroatoms	60	(3)
Delocalized π Electron Systems	63	(3)
Noncovalent Interactions	66	(11)
Chapter Summary	70	(7)
The Conformations of Organic Molecules	77	(28)
Conformations of Acyclic Compounds	77	(5)
Conformations of Cyclic Compounds	82	(5)
Conformations of Substituted Cyclohexanes	87	(10)
Conformations of Other Cyclic Compounds	97	(8)
Chapter Summary	100	(5)
The Stereochemistry of Organic Molecules	105	(32)
Geometric Isomers of Alkenes	105	(5)
Chirality and Enantiomers	110	(13)
Diastereomers	123	(4)
Fischer Projections	127	(2)
Reaction Stereochemistry: A Preview	129	(8)
Chapter Summary	130	(7)
Chemical Reactions and Mechanisms	137	(40)
General Aspects of Reactions	137	(6)
Acid-Base Reactions	143	(11)
Reaction Mechanisms	154	(5)
Reaction Coordinate Diagrams	159	(6)
Reactions In Biological Systems	165	(12)
Chapter Summary	171	(6)
Substitution Reactions of Alkyl Halides	177	(34)
Fundamental Aspects of Substitution Reactions	177	(6)
The SN1 Reaction of Alkyl Halides	183	(13)
The SN2 Reaction of Alkyl Halides	196	(8)
A Comparison of The SN1 and SN2 Mechanisms	204	(7)
Chapter Summary	205	(6)
Substitution Reactions of Alcohols and Related Compounds	211	(28)
Substitution Reactions of Alcohols	211	(7)
Substitution Reactions of Ethers and Epoxides	218	(8)
Substitution Reactions of Thiols and Thioethers	226	(2)
Substitution Reactions In Biochemical Systems	228	(11)
Chapter Summary	231	(8)
Elimination Reactions of Alkyl Halides, Alcohols, and Related Compounds	239	(28)
The E1 Reaction	240	(6)
The E2 Reaction	246	(7)
Substitution Versus Elimination	253	(4)
Elimination Reactions In Biology	257	(10)
Chapter Summary	259	(8)
Addition Reactions of Alkenes and Alkynes	267	(36)
Electrophilic Addition Reactions of Alkenes	267	(9)
Electrophilic Addition Reactions of Alkynes	276	(3)
The Formation of Carbon--Carbon Bonds	279	(6)
Hydroboration Reactions of π Bonds	285	(8)
The Addition of Carbenes To π Bonds	293	(10)
Chapter Summary	295	(8)
Addition Reactions of Conjugated Dienes	303	(28)
The Structures of Dienes	303	(4)
Bonding In Conjugated Dienes	307	(6)
Electrophilic Addition To Conjugated Dienes	313	(4)
The Diels--Alder Reaction	317	(14)
Chapter Summary	324	(7)
Oxidation and Reduction Reactions	331	(32)
Oxidation States in Organic Molecules	331	(3)
Hydrogenation Reactions	334	(4)
Oxidation Reactions of Alkenes	338	(8)
Oxidations Reactions of Alcohols	346	(7)
Oxidation Reactions of Amines	353	(10)
Chapter Summary	355	(8)
Free Radical Reactions	363	(34)
Free Radical Halogenation Reactions	363	(11)
Reduction Via Radical Intermediates	374	(4)
Free Radical Addition Reactions	378	(4)
Oxidation Via Radical Intermediates	382	(15)
Chapter Summary	389	(8)
Proton and Carbon NMR Spectroscopy	397	(48)
Chemical Shifts and Proton Equivalence	398	(10)
Spin Coupling in Simple Systems	408	(5)
Interpreting and Predicting 1H NMR Spectra	413	(7)
Spin Coupling In More Complex Systems	420	(6)
Carbon NMR Spectra	426	(4)
Interpreting 13C NMR Spectra	430	(15)
Chapter Summary	435	(10)
Determining The Structures of Organic Molecules	445	(42)
Analytical Data In Structure Determinations	445	(4)
Mass Spectrometry	449	(9)
Infrared Spectroscopy	458	(12)
Combined Structure Determination Exercises	470	(17)
Chapter Summary	478	(9)
Organometallic Reagents and Chemical Synthesis	487	(38)
Carbon--Carbon Bond Formation	487	(2)
Organomagnesium and Lithium Compounds	489	(9)
Transition Metal Organometallic Compounds	498	(8)
Retrosynthesis	506	(5)
Selectivity Criteria In Synthesis	511	(14)
Chapter Summary	516	(9)
Asymmetric Reactions and Synthesis	525	(36)
Chiral Compounds	525	(3)
Enantiomeric Resolution	528	(2)
Asymmetric Synthesis	530	(8)
Enantioselective Addition Reactions	538	(10)
Synthetic Design of Chiral Molecules	548	(13)
Chapter Summary	554	(7)
The Chemistry of Benzene and Its Derivatives	561	(44)
Structural Aspects of Aromatic Molecules	562	(7)
Electrophilic Substitution Reactions of Benzene	569	(5)
Electrophilic Substitution Reactions of Benzene Derivatives	574	(13)
Other Reactions of Benzene and Its Derivatives	587	(18)
Chapter Summary	594	(11)
Nucleophilic Addition Reactions of Aldehydes and Ketones	605	(30)
General Aspects of Nucleophilic Addition Reactions	606	(2)
Nucleophilic Addition Reactions	608	(4)
Reduction Reactions of Aldehydes and Ketones	612	(10)
Oxidation Reactions of Aldehydes and Ketones	622	(13)
Chapter Summary	625	(10)
Addition--Substitution Reactions of Aldehydes and Ketones: Carbohydrate Chemistry	635	(34)
Hemiacetals and Acetals	636	(4)
Acetals As Protecting Groups	640	(3)
Carbohydrates	643	(8)
Glycosides	651	(7)
Oxidation and Reduction Reactions of Carbohydrates	658	(11)
Chapter Summary	661	(8)
Addition-Elimination Reactions of Aldehydes and Ketones	669	(32)
Compounds With Carbon-Nitrogen Double Bonds	669	(6)
Imine Chemistry and Biochemistry	675	(7)
Enamines	682	(2)
Ylides	684	(17)
Chapter Summary	691	(10)
Addition-Elimination Reactions of Carboxylic Acids and Derivatives	701	(44)
General Aspects of Structure and Reactivity	702	(4)
Reactions of Carboxylic Acids	706	(4)
The Chemistry of Acid Chlorides, Thioesters, and Anhydrides	710	(5)
The Chemistry of Esters	715	(4)
The Chemistry of Amides	719	(5)
The Chemistry of Nitriles	724	(1)
Reactions With Organometallic Compounds	725	(3)
Reduction Reactions of Carboxylic Acids and Derivatives	728	(17)
Chapter Summary	731	(14)
The Acid-Base Chemistry of Carbonyl Compounds	745	(42)
Acidity of Carbonyl Compounds	745	(6)
Enols and Enolate Ions	751	(8)
Reactions of Enolate Ions	759	(7)
Dicarbonyl Compounds	766	(6)
Reactions of Amide and Imide Ions	772	(15)
Chapter Summary	775	(12)
The Nucleophilic Addition Reactions of Enolate Ions	787	(36)
The Aldol Reaction	787	(4)
Crossed-Aldol Reactions	791	(11)
The Claisen Condensation	802	(4)
Crossed-Claisen Condensations	806	(17)
Chapter Summary	816	(7)
Conjugate Addition Reactions of Unsaturated Carbonyl Compounds	823	(36)
α, β-Unsaturated Carbonyl Compounds	824	(3)
Conjugate Addition Reactions	827	(7)
Conjugate Addition Reactions of Carbanions	834	(9)
Reduction Reactions	843	(16)
Chapter Summary	848	(11)
The Chemistry of Polycyclic and Heterocyclic Arenes	859	(34)
Polycyclic Aromatic Compounds	859	(5)
Pyridine and Related Heterocycles	864	(9)
Pyrrole and Related Heterocycles	873	(6)
Azoles	879	(14)
Chapter Summary	886	(7)
Polymers and Polymerization	893	(28)
Polymers and Their Properties	893	(5)
Chain-Growth Polymerization	898	(6)
Step-Growth Polymerization	904	(7)
Modification of Polymers	911	(10)
Chapter Summary	914	(7)
Amino Acids, Peptides, and Proteins	921	(32)
Amino Acids	921	(6)
Chemical Synthesis of Amino Acids	927	(3)
Asymmetric Synthesis of Amino Acids	930	(5)
Peptide Synthesis and Analysis	935	(7)
Protein Structures	942	(11)
Chapter Summary	947	(6)
Nucleic Acids and Molecular Recognition	953
Nucleosides and Nucleotides	953	(8)
Nucleic Acid Structures	961	(8)
Molecular Recognition	969	(1)
Crown Ethers and Cryptands	969	(5)
Cavity-Containing Molecules	974	(3)
Recognition Using Hydrogen Bonds	977
Chapter Summary	982
Appendix	1	(1)
Glossary	1	(1)
Index	1