Organic Chemistry (with Organic ChemistryNOW)

by Hornback, Joseph M.

• ISBN13: 9780534389512
• ISBN10: 0534389511
• Edition: 2nd
• Format: Hardcover
• Copyright: 2005-01-31
• Publisher: Cengage Learning

Summary

ORGANIC CHEMISTRY, Second Edition - the first mechanistic-oriented book written at a level that organic chemistry students will understand! Specifically, the focus on mechanisms is a unifying theme, rather then just an organizing principle. Organizationally mainstream, it is unique in bringing in mechanisms as a unifying principle, and reactions are organized by mechanism type not by functional groups. And now, text/media integration has never been so seamless with the introduction of Organic ChemistryNow for ORGANIC CHEMISTRY, Second Edition.

Table of Contents

PREFACE	xxvi
1 A SIMPLE MODEL FOR CHEMICAL BONDS	1	(29)
1.1 The Field of Organic Chemistry	1	(2)
1.2 Simple Atomic Structure	3	(1)
1.3 Ionic Bonding	4	(1)
1.4 Covalent Bonding	5	(1)
1.5 Lewis Structures	6	(5)
1.6 Covalent Ions	11	(1)
1.7 Formal Charges	11	(4)
1.8 Resonance	15	(2)
1.9 Polar Bonds	17	(1)
1.10 Shapes of Molecules	18	(4)
1.11 Dipole Moments	22	(2)
Review of Mastery Goals	24	(1)
Additional Problems	25	(5)
2 ORGANIC COMPOUNDS: A FIRST LOOK	30	(31)
2.1 Common Bonding Situations	30	(3)
2.2 Bond Strengths and Bond Lengths	33	(1)
2.3 Constitutional Isomers	34	(5)
2.4 Degree of Unsaturation	39	(5)
2.3 Physical Properties and Molecular Structure	44	(2)
2.6 Melting Points, Boiling Points, and Solubilities	46	(4)
Focus On: Boiling Points of Fuels	48	(2)
2.7 Introduction to Functional Groups	50	(2)
Review of Mastery Goals	52	(1)
Additional Problems	53	(8)
3 ORBITALS AND BONDING	61	(42)
3.1 Atomic Orbitals	61	(4)
3.2 Molecular Orbitals	65	(4)
3.3 Single Bonds and sp3 Hybridization	69	(2)
3.4 Double Bonds and sp2 Hybridization	71	(5)
3.5 Triple Bonds and sp Hybridization	76	(2)
3.6 Resonance and MO Theory	78	(3)
3.7 Rules for Resonance Structures	81	(5)
3.8 Types of Resonance Interactions	86	(9)
Focus On: Resonance and the Bond Lengths of Naphthalene	94	(1)
3.9 Molecular Orbital Energies	95	(2)
Review of Mastery Goals	97	(1)
Additional Problems	97	(6)
4 THE ACID-BASE REACTION	103	(39)
4.1 Definitions	103	(4)
4.2 The Acid-Base Equilibrium	107	(4)
4.3 Rate of the Acid-Base Reaction	111	(3)
4.4 Effect of the Atom Bonded to the Hydrogen on Acidity	114	(2)
4.5 Inductive Effects	116	(3)
4.6 Hydrogen Bonding	119	(1)
4.7 Hybridization	120	(1)
4.8 Resonance	120	(8)
Focus On: Calcium Carbide	121	(7)
4.9 Tables of Acids and Bases	128	(4)
4.10 Acidity and Basicity of Functional Groups and Solvents	132	(3)
Review of Mastery Goals	135	(1)
Additional Problems	135	(7)
5 FUNCTIONAL GROUPS AND NOMENCLATURE I	142	(36)
5.1 Alkanes	142	(3)
5.2 Common Nomenclature of Alkanes	145	(1)
5.3 Systematic Nomenclature of Alkanes	146	(9)
Focus On: The Energy Content of Fuels	146	(9)
5.4 Systematic Nomenclature of Cycloalkanes	155	(2)
5.5 Alkenes	157	(3)
5.6 Alkynes	160	(1)
5.7 Alkyl Halides	161	(1)
5.8 Alcohols	162	(5)
Focus On Biological Chemistry: Chlorinated Organic Compounds	164	(3)
5.9 Ethers	167	(1)
5.10 Amines	168	(3)
Review of Mastery Goals	171	(1)
Additional Problems	172	(6)
6 STEREOCHEMISTRY I: CIS-TRANS ISOMERS AND CONFORMATIONS	178	(41)
6.1 Cis-Trans Isomers	179	(4)
6.2 Designating the Configuration of Cis-Trans Isomers	183	(3)
6.3 Conformations	186	(7)
6.4 Conformations of Cyclic Molecules	193	(3)
6.5 Conformations of Cyclohexane	196	(5)
6.6 Conformations of Other Rings	201	(1)
6.7 Conformations of Cyclohexanes with One Substituent	202	(3)
6.8 Conformations of Cyclohexanes with Two or More Substituents	205	(9)
Focus On: How Much Strain Is Too Much?	206	(8)
Review of Mastery Goals	214	(1)
Additional Problems	214	(5)
7 STEREOCHEMISTRY II: CHIRAL MOLECULES	219	(38)
7.1 Chiral Molecules	219	(2)
7.2 Recognizing Chiral Molecules	221	(3)
7.3 Designating Configuration of Enantiomers	224	(3)
7.4 Properties of Enantiomers	227	(3)
7.5 Molecules with Multiple Chirality Centers	230	(4)
7.6 Stereoisomers and Cyclic Compounds	234	(2)
7.7 Resolution: Separating Enantiomers	236	(1)
7.8 Fischer Projections	237	(5)
Focus On: The Historical Development of Understanding Stereochemistry	238	(4)
7.9 Reactions That Produce Enantiomers	242	(2)
Focus On: Pharmaceuticals and Chirality	243	(1)
7.10 Other Chiral Compounds	244	(3)
Review of Mastery Goals	247	(1)
Visual Summary of Isomers	248	(1)
Additional Problems	249	(8)
8 NUCLEOPHILIC SUBSTITUTION REACTIONS: REACTIONS OF ALKYL HALIDES, ALCOHOLS, AND RELATED COMPOUNDS	257	(56)
8.1 The General Reaction	257	(2)
8.2 Reaction Mechanisms	259	(1)
8.3 Bimolecular Nucleophilic Substitution	259	(2)
8.4 Stereochemistry of the SN2 Reaction	261	(3)
8.5 Effect of Substituents on the Rate of the SN2 Reaction	264	(4)
8.6 Unimolecular Nucleophilic Substitution	268	(4)
8.7 Effect of Substituents on the Rate of the SN1 Reaction	272	(4)
Focus On: The llriphenyhnethyl Carbocation	274	(2)
8.8 Stereochemistry of the SN1 Reaction	276	(3)
8.9 Leaving Groups	279	(5)
8.10 Nucleophiles	284	(2)
8.11 Effect of Solvent	286	(3)
8.12 Competition between SN1 and SN2 Reactions	289	(3)
8.13 Intramolecular Reactions	292	(2)
8.14 Competing Reactions	294	(7)
Focus On: Carbocation Rearrangements in Superacids	299	(2)
Review of Mastery Goals	301	(1)
Visual Summary of Key Reactions	301	(1)
Additional Prohknis	302	(11)
9 ELIMINATION REACTIONS: REACTIONS OF ALKYL HALIDES, ALCOHOLS, AND RELATED COMPOUNDS	313	(35)
9.1 The General Reaction	313	(1)
9.2 Bimolecular Elimination	314	(2)
Focus On Biological Chemistry: DDT Resistant Insects	316	(1)
9.3 Stereochemistry of the E2 Reaction	316	(7)
9.4 Direction of Elimination	323	(6)
9.5 Unimolecular Elimination	329	(2)
9.6 Regiochemistry and Stereochemistry of the El Reaction	331	(3)
Focus On: The Elcb Mechanism	333	(1)
9.7 The Competition between Elimination and Substitution	334	(6)
Focus On Biological Chemistry: Biological Elimination
Reactions	340	(1)
Review of Mastery Goals	341	(1)
Visual Summary of Key Reactions	341	(1)
Additional Problems	341	(7)
10 SYNTHETIC USES OF SUBSTITUTION AND ELIMINATION REACTIONS: INTERCONVERTING FUNCTIONAL GROUPS	348	(56)
10.1 Substitution Reactions	348	(1)
10.2 Preparation of Alcohols	349	(3)
10.3 Preparation of Ethers	352	(5)
10.4 Preparation of Esters	357	(1)
10.5 Preparation of Alkyl Halides	358	(4)
10.6 Preparation of Amines	362	(6)
Focus On Biological Chemistry: Biological Alkylations and Poisons	365	(3)
10.7 Preparation of Hydrocarbons	368	(1)
10.8 Formation of Carbon-Carbon Bonds	369	(2)
10.9 Phosphorus and Sulfur Nucleophiles	371	(1)
10.10 Ring Opening of Epoxides	372	(4)
Focus On: Uses of Epoxides in Industry	375	(1)
10.11 Elimination of Hydrogen Halides (Dehydrohalogenation)	376	(1)
10.12 Preparation of Alkynes	377	(1)
10.13 Dehydration	378	(2)
10.14 Eliminations to Form Carbon-Oxygen Double Bonds; Oxidation Reactions	380	(5)
Focus On: Environmentally Friendly Chemistry (Green Chemistry)	384	(1)
10.15 The Strategy of Organic Synthesis	385	(4)
Review of Mastery Goals	389	(1)
Visual Summary of Key Reactions	390	(4)
Integrated Practice Problem	394	(1)
Additional Problems	395	(9)
11 ADDITIONS TO CARBON-CARBON DOUBLE AND TRIPLE BONDS: REACTIONS OF ALKENES AND ALKYNES	404	(62)
11.1 The General Mechanism	405	(1)
11.2 Addition of Hydrogen Halides	406	(6)
11.3 Addition of Water (Hydration)	412	(1)
11.4 Addition of Halogens	413	(6)
11.5 Halohydrin Formation	419	(4)
Focus On: Industrial Addition Reactions	421	(2)
11.6 Oxymercuration-Reduction	423	(3)
11.7 Hydroboration-Oxidation	426	(9)
Focus On: Chiral Boranes in Organic Synthesis	433	(2)
11.8 Addition of Carbenes	435	(3)
11.9 Epoxidation	438	(1)
11.10 Hydroxylation	439	(2)
11.11 Ozonolysis	441	(3)
11.12 Catalytic Hydrogenation	444	(2)
11.13 Additions to Conjugated Dienes	446	(5)
Focus On: Asymmetric Hydrogenation	449	(2)
11.14 Synthesis	451	(2)
Review of Mastery Goals	453	(1)
Visual Summary of Key Reactions	454	(3)
Integrated Practice Problem	457	(1)
Additional Problems	458	(8)
12 FUNCTIONAL GROUPS AND NOMENCLATURE II	466	(34)
12.1 Aromatic Hydrocarbons	466	(6)
Focus On: Structure Proof by the Number of Isomers	469	(3)
12.2 Phenols	472	(1)
12.3 Aldehydes and Ketones	473	(4)
12.4 Carboxylic Acids	477	(2)
12.5 Derivatives of Carboxylic Acids	479	(9)
Focus On: Fragrant Organic Compounds	486	(2)
12.6 Sulfur and Phosphorus Compounds	488	(3)
12.7 Nomenclature of Compounds with Several Functional Groups	491	(9)
Review of Mastery Goals	494	(1)
Additional Problems	494	(6)
13 INFRARED SPECTROSCOPY	500	(43)
13.1 Electromagnetic Radiation	501	(1)
13.2 Interaction of Electromagnetic Radiation with Molecules	502	(1)
13.3 The Electromagnetic Spectrum	503	(2)
13.4 Infrared Spectroscopy	505	(2)
13.5 Generalizations	507	(1)
13.6 The Hydrogen Region	508	(7)
13.7 The Triple-Bond Region	515	(3)
Focus On: Remote Sensing of Automobile Pollutants	516	(2)
13.8 The Double-Bond Region	518	(2)
13.9 The Fingerprint Region	520	(1)
13.10 Interpretation of IR Spectra	521	(12)
Review of Mastery Goals	533	(1)
Additional Problems	533	(10)
14 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY	543	(66)
14.1 Proton Magnetic Resonance Spectroscopy	543	(2)
14.2 Theory of ¹H-NMR	545	(2)
14.3 The Chemical Shift	547	(9)
14.4 Spin Coupling	556	(6)
14.5 Complex Coupling	562	(1)
14.6 Chemical Exchange	563	(1)
14.7 Deuterium	563	(3)
Focus On: NMR Spectroscopy of Carbocations in Superacid	565	(1)
14.8 Interpretation of ¹H-NMR Spectra	566	(8)
Focus On: Magnetic Resonance Imaging	572	(2)
14.9 Carbon-13 Magnetic Resonance Spectroscopy	574	(9)
14.10 Solved Problems Employing IR and NMR Spectra	583	(12)
Review of Mastery Goals	595	(1)
Additional Problems	596	(13)
15 ULTRAVIOLET-VISIBLE SPECTROSCOPY AND MASS SPECTROMETRY	609
15.1 Ultraviolet-Visible Spectroscopy	609	(3)
15.2 Types of Electronic Transitions	612	(3)
15.3 UV Visible Spectroscopy in Structure Determination	615	(2)
Focus On: Ozone, Ultraviolet Radiation, and Sunscreens	616	(1)
15.4 Mass Spectrometry	617	(2)
15.5 Determining the Molecular Formula	619	(5)
15.6 Fragmentation of the Molecular Ion	624	(10)
Focus On: Gas Chromatography and Mass Spectrometry	633	(1)
Review of Mastery Goals	634	(1)
Additional Problems	634
16 BENZENE AND AROMATIC COMPOUNDS	042	(629)
16.1 Benzene	642	(2)
16.2 Resonance Energy of Benzene	644	(2)
16.3 Molecular Orbital Model for Cyclic Conjugated Molecules	646	(3)
16.4 Cyclobutadiene	649	(2)
16.5 Hackel's Rule	651	(1)
16.6 Cyclooctatetraene	652	(1)
16.7 Heterocyclic Aromatic Compounds	653	(2)
16.8 Polycyclic Aromatic Hydrocarbons	655	(2)
Focus On: Carcinogenic Polycyclic Aromatic Hydrocarbons	657	(1)
16.9 NMR and Aromaticity	657	(2)
16.10 Annulenes	659	(2)
16.11 Aromatic and Antiaromatic Ions	661	(4)
Focus On: Buckminsterfullerene, a New Form of Carbon	663	(2)
Review of Mastery Goals	665	(1)
Additional Problems	665	(6)
17 AROMATIC SUBSTITUTION REACTIONS	671	(68)
17.1 Mechanism for Electrophilic Aromatic Substitution	671	(3)
17.2 Effect of Substituents	674	(8)
17.3 Effect of Multiple Substituents	682	(1)
17.4 Nitration	683	(3)
17.5 Halogenation	686	(3)
17.6 Sulfonation	689	(1)
17.7 Friedel-Crafts Allrylation	690	(6)
Focus On: Synthetic Detergents, BHT, and BHA	694	(2)
17.8 Friedel-Crafts Acylation	696	(3)
17.9 Electrophilic Substitutions of Polycyclic Aromatic Compounds	699	(1)
17.10 Nucleophilic Aromatic Substitution: Diazonium Ions	700	(3)
17.11 Nucleophilic Aromatic Substitution: Addition-Elimination	703	(2)
17.12 Nucleophilic Aromatic Substitution: Elimination-Addition	705	(4)
Focus On: Experimental Evidence for the Benzyne Mechanism	708	(1)
17.11 Some Additional Useful Reactions	709	(4)
17.14 Synthesis of Aromatic Compounds	713	(6)
Review of Mastery Goals	719	(1)
Visual Summary of Key Reactions	719	(4)
Intergrated Practice Problem	723	(1)
Additional Problems	724	(15)
18 ADDITIONS TO THE CARBONYL GROUPS REACTIONS OF ALDEHYDES AND KETONES	739	(64)
18.1 General Mechanisms	740	(2)
18.2 Addition of Hydride; Reduction of Aldehydes and Ketones	742	(2)
18.3 Addition of Water	744	(4)
18.4 Addition of Hydrogen Cyanide	748	(3)
18.5 Preparation and Properties of Organometallic Nucleophiles	751	(2)
18.6 Addition of Organometallic Nucleophiles	753	(5)
18.7 Addition of Phosphorus Ylides; The Wittig Reaction	758	(7)
Focus On: Synthesis of Vitamin A	763	(2)
18.8 Addition of Nitrogen Nucleophiles	765	(10)
Focus On Biological Chemistry: Imines in Living Organisms	773	(2)
18.9 Addition of Alcohols	775	(4)
18.10 Conjugate Additions	779	(5)
18.11 Synthesis	784	(3)
Review of Mastery Goals	787	(1)
Visual Summary of Key Reactions	787	(2)
Integrated Practice Problem	789	(1)
Additional Problems	790	(13)
19 SUBSTITUTIONS AT THE CARBONYL GROUP: REACTIONS OF CARBOXYLIC ACIDS AND DERIVATIVES	803	(55)
19.1 The General Mechanism	803	(5)
19.2 Preparation of Acyl Chlorides	808	(2)
19.3 Preparation of Anhydrides	810	(1)
19.4 Preparation of Esters	811	(4)
19.5 Preparation of Carboxylic Acids	815	(9)
Focus On: The Preparation of Soap	819	(5)
19.6 Preparation of Amides	824	(2)
19.7 Reaction with Hydride Nucleophiles	826	(4)
19.8 Reduction of Acid Derivatives to Aldehydes	830	(2)
19.9 Reactions with Organometallic Nucleophiles	832	(2)
19.10 Preparation of Ketones	834	(2)
19.11 Derivatives of Sulfur and Phosphorus Acids	836	(4)
Focus On Biological Chemistry: Nerve Gases and Pesticides	838	(2)
Review of Mastery Goals	840	(1)
Visual Summary of Key Reactions	840	(3)
Integrated Practice Problem	843	(1)
Additional Problems	843	(15)
20 ENOLATE AND OTHER CARBON NUCLEOPHILES	858	(60)
20.1 Enols and Enolate Anions	859	(3)
20.2 Halogenation of the a-Carbon	862	(2)
20.3 Alkylation of Enolate Anions	864	(3)
20.4 Alkylation of More Stabilized Anions	867	(6)
20.5 The Aldol Condensation	873	(7)
Focus On Biological Chemistry: The Reverse Aldol Reaction in Metabolism	880	(1)
20.6 Ester Condensations	880	(7)
Focus On: An Industrial Aldol Reaction	886	(1)
20.7 Carbon and Hydrogen Leaving Groups	887	(2)
20.8 Enamines	889	(2)
20.9 Other Carbon Nucleophiles	891	(3)
20.10 Conjugate Additions	894	(4)
20.11 Synthesis	898	(4)
Review of Mastery Goals	902	(1)
Visual Summary of Key Reactions	902	(2)
Integrated Practice Problem	904	(1)
Additional Problems	905	(13)
21 THE CHEMISTRY OF RADICALS	918	(38)
21.1 Radicals	918	(1)
21.2 Stability of Radicals	919	(2)
21.3 Geometry of Carbon Radicals	921	(1)
21.4 Generation of Radicals	922	(1)
213 General Radical Reactions	923	(4)
Focus On: The 'Itiphenylmethyl Radical	926	(1)
21.6 Halogenation	927	(7)
21.7 Dehalogenation	934	(1)
21.8 Autoxidation	935	(4)
Focus On Biological Chemistry: Vitamin E and Lipid Autoxidation	937	(2)
21.9 Radical Additions to Alkenes	939	(2)
21.10 Reductions and Radical Anions	941	(5)
Review of Mastery Goals	946	(1)
Visual Summary of Key Reactions	947	(1)
Additional Problems	948	(8)
22 PERICYCLIC REACTIONS	956	(55)
22.1 Pericyclic Reactions	956	(3)
22.2 MO Theory for Conjugated Molecules	959	(6)
22.3 Electrocyclic Reactions	965	(5)
22.4 Examples of Electrocyclic Reactions	970	(5)
Focus On: Dewar Benzene	973	(2)
22.5 Cycloaddition Reactions	975	(2)
22.6 The Diels-Alder Reaction	977	(7)
22.7 Other Cycloaddition Reactions	984	(2)
22.8 Sigmatropic Rearrangements	986	(4)
22.9 Examples of Sigmatropic Rearrangements	990	(4)
Focus On Biological Chemistry: Pericyclic Reactions and Vitamin D	993	(1)
22.10 Rearrangements to Electron-Deficient Centers	994	(5)
Review of Mastery Goals	999	(1)
Visual Summary of Key Reactions	999	(2)
Additional Problems	1001	(10)
23 THE SYNTHESIS OF ORGANIC COMPOUNDS	1011	(42)
23.1 Protecting Groups for Alcohols	1011	(4)
23.2 Protecting Groups for Aldehydes and Ketones	1015	(1)
23.3 Protecting Groups for Carboxylic Acids	1016	(2)
23.4 Protecting Groups for Amines	1018	(2)
23.5 Retrosynthetic Analysis	1020	(6)
Focus On Biological Chemistry: Pheromones	1025	(1)
23.6 Examples of Syntheses	1026	(3)
23.7 Reactions That Form Carbon-Carbon Bonds	1029	(1)
23.8 Preparation of Functional Groups	1030	(15)
Review of Mastery Goals	1045	(1)
Additional Problems	1046	(7)
24 SYNTHETIC POLYMERS	1053	(32)
24.1 Radical Chain Polymerization	1053	(4)
24.2 Structures of Polymers	1057	(3)
24.3 Ionic Polymerization	1060	(2)
Focus On: Super Glue	1062	(1)
24.4 Coordination Polymerization	1062	(2)
24.5 Physical Properties of Polymers	1064	(2)
24.6 Major Thermoplastic Addition Polymers	1066	(2)
24.7 Elastomers	1068	(2)
24.8 Condensation Polymers	1070	(5)
24.9 Thermoset Polymers	1075	(2)
24.10 Chemical Properties of Polymers	1077	(4)
Focus On: Recycling Plastics	1080	(1)
Review of Mastery Goals	1081	(1)
Additional Problems	1081	(4)
25 CARBOHYDRATES	1085	(38)
25.1 Structures of Carbohydrates	1085	(1)
25.2 Stereochemistry of Carbohydrates	1086	(4)
25.3 Cyclization of Monosaccharides	1090	(4)
25.4 Reactions of Monosaccharides	1094	(11)
Focus On: The Determination of Anomer Configuration	1095	(8)
Focus On: Artificial Sweeteners	1103	(2)
25.5 Fischer's Structure Proof for Glucose	1105	(5)
25.6 Disaccharides	1110	(1)
25.7 Polysaccharides	1111	(2)
25.8 Other Carbohydrate-Containing Compounds	1113	(10)
Focus On Biological Chemistry: Blood Groups	1115	(1)
Review of Mastery Goals	1116	(1)
Additional Problems	1117	(6)
26 AMINO ACIDS, PEPTIDES, AND PROTEINS	1123	(39)
26.1 Amino Acids	1123	(3)
26.2 Acid-Base Chemistry of Amino Acids	1126	(4)
26.3 Chemical Reactions of Amino Acids	1130	(1)
26.4 Laboratory Synthesis of Amino Acids	1131	(6)
Focus On: Asymmetric Synthesis of Amino Acids	1135	(2)
26.5 Peptides and Proteins	1137	(3)
Focus On: NMR Spectra of Amides	1140	(1)
26.6 Sequencing Peptides	1140	(8)
26.7 Laboratory Synthesis of Peptides	1148	(7)
26.8 Protein Structure	1155	(1)
26.9 Enzymes	1156	(2)
Review of Mastery Goals	1158	(1)
Additional Problems	1158	(4)
27 NUCLEOTIDES AND NUCLEIC ACIDS	1162	(22)
27.1 Nucleosides and Nucleotides	1162	(3)
27.2 Structure of DNA and RNA	1165	(6)
Focus On: Tautomers of Guanine and Thymine	1170	(1)
27.3 Replication, Transcription, and Translation	1171	(4)
Focus On Biological Chemistry: Treatment of AIDS with AZT	1174	(1)
27.4 Sequencing DNA	1175	(3)
27.5 Laboratory Synthesis of DNA	1178	(2)
Review of Mastery Goals	1180	(1)
Additional Problems	1181	(3)
28 OTHER NATURAL PRODUCTS	1184
28.1 Terpenes	1184	(2)
28.2 Monoterpenes	1186	(4)
28.3 Sesquiterpenes	1190	(4)
28.4 Larger Terpenes	1194	(2)
28.5 Steroids	1196	(6)
Focus On: Syntheses That Mimic Nature	1200	(2)
28.6 Synthesis of Steroids	1202	(4)
Focus On: The Birth Control Pill	1204	(2)
28.7 Alkaloids	1206	(2)
28.8 Fats and Related Compounds	1208	(3)
Focus On: Partially Hydrogenated Vegetable Oil	1210	(1)
28.9 Prostaglandins	1211	(2)
Review of Mastery Goals	1213	(1)
Additional Problems	1213
APPENDIX: ANSWERS TO IN-CHAPTER PROBLEMS A-0
GLOSSARY G-0
INDEX	I-0