|
|
|
|
|
|
3 | (1) |
|
Atomic Structure: Orbitals |
|
|
3 | (2) |
|
Atomic Structure: Electron Configurations |
|
|
5 | (1) |
|
Development of Chemical Bonding Theory |
|
|
6 | (1) |
|
The Nature of Chemical Bonds |
|
|
7 | (3) |
|
|
|
10 | (1) |
|
Hybridization: sp3 Orbitals and the Structure of Methane |
|
|
11 | (1) |
|
Hybridization: sp3 Orbitals and the Structure of Ethane |
|
|
12 | (1) |
|
Hybridization: sp2 Orbitals and the Structure of Ethylene |
|
|
13 | (3) |
|
Hybridization: sp Orbitals and the Structure of Acetylene |
|
|
16 | (1) |
|
Hybridization of Nitrogen and Oxygen |
|
|
17 | (2) |
|
|
|
19 | (10) |
|
Chemistry@Work: Chemicals, Toxicity, and Risk |
|
|
20 | (1) |
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|
|
21 | (2) |
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|
23 | (5) |
|
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|
28 | (1) |
|
|
|
28 | (1) |
|
Polar Covalent Bonds; Acids and Bases |
|
|
|
Polar Covalent Bonds: Electronegativity |
|
|
29 | (3) |
|
Polar Covalent Bonds: Dipole Moments |
|
|
32 | (2) |
|
|
|
34 | (3) |
|
|
|
37 | (2) |
|
Rules for Resonance Forms |
|
|
39 | (1) |
|
|
|
40 | (3) |
|
Acids and Bases: The Bronsted-Lowry Definition |
|
|
43 | (2) |
|
|
|
45 | (1) |
|
Predicting Acid-Base Reactions from pKa Values |
|
|
46 | (2) |
|
Organic Acids and Organic Bases |
|
|
48 | (3) |
|
Acids and Bases: The Lewis Definition |
|
|
51 | (4) |
|
Drawing Chemical Structures |
|
|
55 | (2) |
|
|
|
57 | (11) |
|
Chemistry@Work: Alkaloids: Naturally Occurring Bases |
|
|
58 | (1) |
|
|
|
59 | (1) |
|
|
|
60 | (7) |
|
|
|
67 | (1) |
|
|
|
67 | (1) |
|
Organic Compounds: Alkanes and Cycloalkanes |
|
|
|
|
|
68 | (6) |
|
Alkanes and Alkane Isomers |
|
|
74 | (3) |
|
|
|
77 | (3) |
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|
|
80 | (6) |
|
|
|
86 | (2) |
|
|
|
88 | (1) |
|
|
|
89 | (3) |
|
Cis-Trans Isomerism in Cycloalkanes |
|
|
92 | (11) |
|
|
|
94 | (2) |
|
|
|
96 | (1) |
|
|
|
97 | (5) |
|
|
|
102 | (1) |
|
|
|
102 | (1) |
|
Stereochemistry of Alkanes and Cycloalkanes |
|
|
|
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|
103 | (2) |
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|
105 | (1) |
|
|
|
106 | (3) |
|
Stability of Cycloalkanes: The Baeyer Strain Theory |
|
|
109 | (2) |
|
The Nature of Ring Strain |
|
|
111 | (1) |
|
Cyclopropane: An Orbital View |
|
|
112 | (1) |
|
Conformations of Cyclobutane and Cyclopentane |
|
|
113 | (2) |
|
Conformations of Cyclohexane |
|
|
115 | (1) |
|
Axial and Equatorial Bonds in Cyclohexane |
|
|
116 | (2) |
|
Conformational Mobility of Cyclohexane |
|
|
118 | (1) |
|
Conformations of Monosubstituted Cyclohexanes |
|
|
119 | (3) |
|
Conformational Analysis of Disubstituted Cyclohexanes |
|
|
122 | (3) |
|
|
|
125 | (1) |
|
Conformations of Polycyclic Molecules |
|
|
126 | (9) |
|
Chemistry@Work: Molecular Mechanics |
|
|
128 | (1) |
|
|
|
129 | (1) |
|
|
|
130 | (4) |
|
|
|
134 | (1) |
|
|
|
134 | (1) |
|
An Overview of Organic Reactions |
|
|
|
Kinds of Organic Reactions |
|
|
135 | (1) |
|
How Organic Reactions Occur: Mechanisms |
|
|
136 | (2) |
|
Radical Reactions and How They Occur |
|
|
138 | (1) |
|
Polar Reactions and How They Occur |
|
|
139 | (5) |
|
An Example of a Polar Reaction: Addition of HBr to Ethylene |
|
|
144 | (3) |
|
Using Curved Arrows in Polar Reaction Mechanisms |
|
|
147 | (3) |
|
Describing a Reaction: Equilibria, Rates, and Energy Changes |
|
|
150 | (3) |
|
Describing a Reaction: Bond Dissociation Energies |
|
|
153 | (3) |
|
Describing a Reaction: Energy Diagrams and Transition States |
|
|
156 | (2) |
|
Describing a Reaction: Intermediates |
|
|
158 | (12) |
|
Chemistry@Work: Explosives |
|
|
160 | (2) |
|
|
|
162 | (1) |
|
|
|
163 | (5) |
|
|
|
168 | (1) |
|
|
|
168 | (2) |
|
Alkenes: Structure and Reactivity |
|
|
|
Industrial Preparation and Use of Alkenes |
|
|
170 | (1) |
|
Calculating Degree of Unsaturation |
|
|
171 | (2) |
|
|
|
173 | (2) |
|
Electronic Structure of Alkenes |
|
|
175 | (1) |
|
Cis-Trans Isomerism in Alkenes |
|
|
176 | (1) |
|
Sequence Rules: The E,Z Designation |
|
|
177 | (4) |
|
|
|
181 | (3) |
|
Electrophilic Addition of HX to Alkenes |
|
|
184 | (3) |
|
Orientation of Electrophilic Addition: Markovnikov's Rule |
|
|
187 | (3) |
|
Carbocation Structure and Stability |
|
|
190 | (2) |
|
|
|
192 | (3) |
|
Evidence for the Mechanism of Electrophilic Addition: Carbocation Rearrangements |
|
|
195 | (12) |
|
Chemistry@Work: Terpenes: Naturally Occurring Alkenes |
|
|
197 | (1) |
|
|
|
198 | (1) |
|
|
|
199 | (6) |
|
|
|
205 | (1) |
|
|
|
205 | (2) |
|
Alkenes: Reactions and Synthesis |
|
|
|
Preparation of Alkenes: A Preview of Elimination Reactions |
|
|
207 | (1) |
|
Addition of Halogens to Alkenes |
|
|
208 | (2) |
|
|
|
210 | (2) |
|
Addition of Water to Alkenes: Oxymercuration |
|
|
212 | (3) |
|
Addition of Water to Alkenes: Hydroboration |
|
|
215 | (4) |
|
Addition of Carbenes to Alkenes: Cyclopropane Synthesis |
|
|
219 | (3) |
|
Reduction of Alkenes: Hydrogenation |
|
|
222 | (2) |
|
Oxidation of Alkenes: Hydroxylation and Cleavage |
|
|
224 | (3) |
|
Biological Alkene Addition Reactions |
|
|
227 | (1) |
|
Addition of Radicals to Alkenes: Polymers |
|
|
228 | (18) |
|
Chemistry@Work: Natural Rubber |
|
|
233 | (1) |
|
|
|
234 | (1) |
|
|
|
235 | (2) |
|
|
|
237 | (8) |
|
|
|
245 | (1) |
|
|
|
245 | (1) |
|
Alkynes: An Introduction to Organic Synthesis |
|
|
|
Electronic Structure of Alkynes |
|
|
246 | (1) |
|
|
|
247 | (1) |
|
Preparation of Alkynes: Elimination Reactions of Dihalides |
|
|
248 | (1) |
|
Reactions of Alkynes: Addition of HX and X2 |
|
|
249 | (1) |
|
|
|
250 | (4) |
|
|
|
254 | (2) |
|
Oxidative Cleavage of Alkynes |
|
|
256 | (1) |
|
Alkyne Acidity: Formation of Acetylide Anions |
|
|
257 | (1) |
|
Alkylation of Acetylide Anions |
|
|
258 | (2) |
|
An Introduction to Organic Synthesis |
|
|
260 | (15) |
|
Chemistry@Work: The Art of Organic Synthesis |
|
|
265 | (1) |
|
|
|
266 | (1) |
|
|
|
266 | (2) |
|
|
|
268 | (6) |
|
|
|
274 | (1) |
|
|
|
274 | (1) |
|
|
|
|
Enantiomers and the Tetrahedral Carbon |
|
|
275 | (2) |
|
The Reason for Handedness in Molecules: Chirality |
|
|
277 | (3) |
|
|
|
280 | (1) |
|
Pasteur's Discovery of Enantiomers |
|
|
281 | (1) |
|
Sequence Rules for Specification of Configuration |
|
|
282 | (5) |
|
|
|
287 | (1) |
|
|
|
288 | (2) |
|
Molecules with More than Two Chirality Centers |
|
|
290 | (1) |
|
Physical Properties of Stereoisomers |
|
|
291 | (1) |
|
Racemic Mixtures and Their Resolution |
|
|
291 | (2) |
|
A Brief Review of Isomerism |
|
|
293 | (2) |
|
Stereochemistry of Reactions: Addition of HBr to Alkenes |
|
|
295 | (1) |
|
Stereochemistry of Reactions: Addition of Br2 to Alkenes |
|
|
296 | (2) |
|
Stereochemistry of Reactions: Addition of HBr to a Chiral Alkene |
|
|
298 | (1) |
|
Chirality at Atoms Other Than Carbon |
|
|
299 | (1) |
|
|
|
300 | (1) |
|
|
|
301 | (16) |
|
Chemistry@Work: Chiral Drugs |
|
|
304 | (1) |
|
|
|
305 | (1) |
|
|
|
306 | (9) |
|
|
|
315 | (1) |
|
|
|
315 | (2) |
|
|
|
|
|
|
317 | (2) |
|
Structure of Alkyl Halides |
|
|
319 | (1) |
|
|
|
319 | (1) |
|
Radical Halogenation of Alkanes |
|
|
320 | (3) |
|
Allylic Bromination of Alkenes |
|
|
323 | (2) |
|
Stability of the Allyl Radical: Resonance Revisited |
|
|
325 | (2) |
|
Preparing Alkyl Halides from Alcohols |
|
|
327 | (2) |
|
Reactions of Organohalides: Grignard Reagents |
|
|
329 | (1) |
|
Organometallic Coupling Reactions |
|
|
330 | (2) |
|
Oxidation and Reduction in Organic Chemistry |
|
|
332 | (11) |
|
Chemistry@Work: Naturally Occurring Organohalides |
|
|
335 | (1) |
|
|
|
336 | (1) |
|
|
|
336 | (2) |
|
|
|
338 | (4) |
|
|
|
342 | (1) |
|
|
|
342 | (1) |
|
Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations |
|
|
|
The Discovery of the Walden Inversion |
|
|
343 | (1) |
|
Stereochemistry of Nucleophilic Substitution |
|
|
344 | (2) |
|
Kinetics of Nucleophilic Substitution |
|
|
346 | (1) |
|
|
|
347 | (2) |
|
Characteristics of the SN2 Reaction |
|
|
349 | (7) |
|
|
|
356 | (1) |
|
Kinetics of the SN1 Reaction |
|
|
357 | (2) |
|
Stereochemistry of the SN1 Reaction |
|
|
359 | (2) |
|
Characteristics of the SN1 Reaction |
|
|
361 | (6) |
|
Elimination Reactions of Alkyl Halides: Zaitsev's Rule |
|
|
367 | (2) |
|
|
|
369 | (3) |
|
Elimination Reactions and Cyclohexane Conformation |
|
|
372 | (2) |
|
The Deuterium Isotope Effect |
|
|
374 | (1) |
|
|
|
374 | (2) |
|
Summary of Reactivity: SN1, SN2, E1, E2 |
|
|
376 | (2) |
|
Substitution Reactions in Synthesis |
|
|
378 | (16) |
|
Chemistry@Work: Substitution Reactions in Living Organisms |
|
|
380 | (1) |
|
|
|
381 | (1) |
|
|
|
382 | (1) |
|
|
|
383 | (9) |
|
|
|
392 | (1) |
|
|
|
392 | (2) |
|
Structure Determination: Mass Spectrometry and Infrared Spectroscopy |
|
|
|
|
|
394 | (2) |
|
Interpreting Mass Spectra |
|
|
396 | (1) |
|
Interpreting Mass-Spectral Fragmentation Patterns |
|
|
397 | (3) |
|
Mass-Spectral Behavior of Some Common Functional Groups |
|
|
400 | (3) |
|
Spectroscopy and the Electromagnetic Spectrum |
|
|
403 | (3) |
|
Infrared Spectroscopy of Organic Molecules |
|
|
406 | (1) |
|
Interpreting Infrared Spectra |
|
|
407 | (4) |
|
Infrared Spectra of Hydrocarbons |
|
|
411 | (1) |
|
Infrared Spectra of Some Common Functional Groups |
|
|
412 | (12) |
|
Chemistry@Work: Chromatography: Purifying Organic Compounds |
|
|
415 | (2) |
|
|
|
417 | (1) |
|
|
|
417 | (6) |
|
|
|
423 | (1) |
|
|
|
423 | (1) |
|
Structure Determination: Nuclear Magnetic Resonance Spectroscopy |
|
|
|
Nuclear Magnetic Resonance Spectroscopy |
|
|
424 | (2) |
|
The Nature of NMR Absorptions |
|
|
426 | (3) |
|
|
|
429 | (2) |
|
13C NMR Spectroscopy: Signal Averaging and FT-NMR |
|
|
431 | (1) |
|
Characteristics of 13C NMR Spectroscopy |
|
|
432 | (2) |
|
DEPT 13C NMR Spectroscopy |
|
|
434 | (3) |
|
Uses of 13C NMR Spectroscopy |
|
|
437 | (1) |
|
1H NMR Spectroscopy and Proton Equivalence |
|
|
438 | (2) |
|
Chemical Shifts in 1H NMR Spectroscopy |
|
|
440 | (3) |
|
Integration of 1H NMR Absorptions: Proton Counting |
|
|
443 | (1) |
|
Spin-Spin Splitting in 1H NMR Spectra |
|
|
443 | (5) |
|
More Complex Spin-Spin Splitting Patterns |
|
|
448 | (3) |
|
Uses of 1H NMR Spectroscopy |
|
|
451 | (14) |
|
Chemistry@Work: Magnetic Resonance Imaging (MRI) |
|
|
452 | (1) |
|
|
|
452 | (1) |
|
|
|
453 | (10) |
|
|
|
463 | (1) |
|
|
|
463 | (2) |
|
Conjugated Dienes and Ultraviolet Spectroscopy |
|
|
|
Preparation and Stability of Conjugated Dienes |
|
|
465 | (2) |
|
Molecular Orbital Description of 1,3-Butadiene |
|
|
467 | (2) |
|
Electrophilic Additions to Conjugated Dienes: Allylic Carbocations |
|
|
469 | (3) |
|
Kinetic versus Thermodynamic Control of Reactions |
|
|
472 | (2) |
|
The Diels--Alder Cycloaddition Reaction |
|
|
474 | (1) |
|
Characteristics of the Diels--Alder Reaction |
|
|
475 | (5) |
|
Diene Polymers: Natural and Synthetic Rubbers |
|
|
480 | (2) |
|
Structure Determination in Conjugated Systems: Ultraviolet Spectroscopy |
|
|
482 | (1) |
|
Ultraviolet Spectrum of 1,3-Butadiene |
|
|
483 | (2) |
|
Interpreting Ultraviolet Spectra: The Effect of Conjugation |
|
|
485 | (1) |
|
Conjugation, Color, and the Chemistry of Vision |
|
|
486 | (13) |
|
Chemistry@Work: Photolithography |
|
|
488 | (1) |
|
|
|
489 | (1) |
|
|
|
490 | (1) |
|
|
|
490 | (7) |
|
|
|
497 | (1) |
|
|
|
497 | (2) |
|
|
|
|
Sources of Aromatic Hydrocarbons |
|
|
499 | (1) |
|
Naming Aromatic Compounds |
|
|
500 | (2) |
|
Structure and Stability of Benzene |
|
|
502 | (2) |
|
Molecular Orbital Description of Benzene |
|
|
504 | (1) |
|
Aromaticity and the Huckel 4n + 2 Rule |
|
|
505 | (2) |
|
|
|
507 | (3) |
|
Aromatic Heterocycles: Pyridine and Pyrrole |
|
|
510 | (2) |
|
|
|
512 | (2) |
|
Polycyclic Aromatic Compounds: Naphthalene |
|
|
514 | (1) |
|
Spectroscopy of Aromatic Compounds |
|
|
515 | (14) |
|
Chemistry@Work: Aspirin, NSAIDs, and COX-2 Inhibitors |
|
|
519 | (1) |
|
|
|
520 | (1) |
|
|
|
521 | (6) |
|
|
|
527 | (1) |
|
|
|
527 | (2) |
|
Chemistry of Benzene: Electrophilic Aromatic Substitution |
|
|
|
Bromination of Aromatic Rings |
|
|
529 | (3) |
|
Other Aromatic Substitutions |
|
|
532 | (3) |
|
Alkylation of Aromatic Rings: The Friedel-Crafts Reaction |
|
|
535 | (3) |
|
Acylation of Aromatic Rings |
|
|
538 | (1) |
|
Substituent Effects in Substituted Aromatic Rings |
|
|
539 | (4) |
|
An Explanation of Substituent Effects |
|
|
543 | (6) |
|
Trisubstituted Benzenes: Additivity of Effects |
|
|
549 | (2) |
|
Nucleophilic Aromatic Substitution |
|
|
551 | (2) |
|
|
|
553 | (2) |
|
Oxidation of Aromatic Compounds |
|
|
555 | (3) |
|
Reduction of Aromatic Compounds |
|
|
558 | (1) |
|
Synthesis of Trisubstituted Benzenes |
|
|
559 | (19) |
|
Chemistry@Work: Combinatorial Chemistry |
|
|
564 | (2) |
|
|
|
566 | (1) |
|
|
|
566 | (3) |
|
|
|
569 | (8) |
|
|
|
577 | (1) |
|
|
|
577 | (1) |
|
A Brief Review of Organic Reactions |
|
|
|
A Summary of the Kinds of Organic Reactions |
|
|
578 | (4) |
|
A Summary of Organic Reaction Mechanisms |
|
|
582 | (6) |
|
|
|
586 | (1) |
|
|
|
586 | (1) |
|
|
|
586 | (2) |
|
|
|
|
Naming Alcohols and Phenols |
|
|
588 | (2) |
|
Properties of Alcohols and Phenols: Hydrogen Bonding |
|
|
590 | (1) |
|
Properties of Alcohols and Phenols: Acidity and Basicity |
|
|
591 | (5) |
|
Preparation of Alcohols: A Review |
|
|
596 | (2) |
|
Alcohols from Reduction of Carbonyl Compounds |
|
|
598 | (3) |
|
Alcohols from Reaction of Carbonyl Compounds with Grignard Reagents |
|
|
601 | (4) |
|
Some Reactions of Alcohols |
|
|
605 | (6) |
|
|
|
611 | (2) |
|
|
|
613 | (2) |
|
Preparation and Uses of Phenols |
|
|
615 | (3) |
|
|
|
618 | (1) |
|
Spectroscopy of Alcohols and Phenols |
|
|
619 | (21) |
|
Chemistry@Work: Ethanol: Chemical, Drug, and Poison |
|
|
623 | (1) |
|
|
|
624 | (1) |
|
|
|
625 | (3) |
|
|
|
628 | (10) |
|
|
|
638 | (1) |
|
|
|
638 | (2) |
|
Ethers and Epoxides; Thiols and Sulfides |
|
|
|
|
|
640 | (1) |
|
Structure, Properties, and Sources of Ethers |
|
|
640 | (2) |
|
The Williamson Ether Synthesis |
|
|
642 | (1) |
|
Alkoxymercuration of Alkenes |
|
|
643 | (1) |
|
Reactions of Ethers: Acidic Cleavage |
|
|
644 | (2) |
|
Reactions of Ethers: Claisen Rearrangement |
|
|
646 | (2) |
|
|
|
648 | (1) |
|
Ring-Opening Reactions of Epoxides |
|
|
649 | (5) |
|
|
|
654 | (1) |
|
|
|
655 | (3) |
|
|
|
658 | (14) |
|
Chemistry@Work: Epoxy Resins and Adhesives |
|
|
660 | (1) |
|
|
|
661 | (1) |
|
|
|
662 | (2) |
|
|
|
664 | (7) |
|
|
|
671 | (1) |
|
|
|
671 | (1) |
|
A Preview of Carbonyl Compounds |
|
|
|
Kinds of Carbonyl Compounds |
|
|
672 | (2) |
|
Nature of the Carbonyl Group |
|
|
674 | (1) |
|
General Reactions of Carbonyl Compounds |
|
|
675 | (5) |
|
|
|
680 | (3) |
|
|
|
680 | (1) |
|
|
|
681 | (1) |
|
|
|
681 | (2) |
|
Aldehydes and Ketones: Nucleophilic Addition Reactions |
|
|
|
Naming Aldehydes and Ketones |
|
|
683 | (2) |
|
Preparation of Aldehydes and Ketones |
|
|
685 | (2) |
|
Oxidation of Aldehydes and Ketones |
|
|
687 | (1) |
|
Nucleophilic Addition Reactions of Aldehydes and Ketones |
|
|
688 | (2) |
|
Relative Reactivity of Aldehydes and Ketones |
|
|
690 | (1) |
|
Nucleophilic Addition of H2O: Hydration |
|
|
691 | (2) |
|
Nucleophilic Addition of HCN: Cyanohydrin Formation |
|
|
693 | (2) |
|
Nucleophilic Addition of Grignard Reagents and Hydride Reagents: Alcohol Formation |
|
|
695 | (1) |
|
Nucleophilic Addition of Amines: Imine and Enamine Formation |
|
|
696 | (4) |
|
Nucleophilic Addition of Hydrazine: The Wolff-Kishner Reaction |
|
|
700 | (2) |
|
Nucleophilic Addition of Alcohols: Acetal Formation |
|
|
702 | (4) |
|
Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction |
|
|
706 | (3) |
|
The Cannizzaro Reaction: Biological Reductions |
|
|
709 | (2) |
|
Conjugate Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones |
|
|
711 | (4) |
|
Some Biological Nucleophilic Addition Reactions |
|
|
715 | (1) |
|
Spectroscopy of Aldehydes and Ketones |
|
|
716 | (22) |
|
Chemistry@Work: Enantioselective Synthesis |
|
|
720 | (1) |
|
|
|
721 | (1) |
|
|
|
722 | (3) |
|
|
|
725 | (11) |
|
|
|
736 | (1) |
|
|
|
736 | (2) |
|
Carboxylic Acids and Nitriles |
|
|
|
Naming Carboxylic Acids and Nitriles |
|
|
738 | (2) |
|
Structure and Physical Properties of Carboxylic Acids |
|
|
740 | (1) |
|
Dissociation of Carboxylic Acids |
|
|
741 | (2) |
|
Substituent Effects on Acidity |
|
|
743 | (2) |
|
Substituent Effects in Substituted Benzoic Acids |
|
|
745 | (1) |
|
Preparation of Carboxylic Acids |
|
|
746 | (3) |
|
Reactions of Carboxylic Acids: An Overview |
|
|
749 | (1) |
|
Reduction of Carboxylic Acids |
|
|
749 | (1) |
|
|
|
750 | (5) |
|
Spectroscopy of Carboxylic Acids and Nitriles |
|
|
755 | (16) |
|
Chemistry@Work: Vitamin C |
|
|
757 | (1) |
|
|
|
758 | (1) |
|
|
|
759 | (2) |
|
|
|
761 | (8) |
|
|
|
769 | (1) |
|
|
|
769 | (2) |
|
Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions |
|
|
|
Naming Carboxylic Acid Derivatives |
|
|
771 | (3) |
|
Nucleophilic Acyl Substitution Reactions |
|
|
774 | (5) |
|
Nucleophilic Acyl Substitution Reactions of Carboxylic Acids |
|
|
779 | (4) |
|
Chemistry of Acid Halides |
|
|
783 | (5) |
|
Chemistry of Acid Anhydrides |
|
|
788 | (1) |
|
|
|
789 | (6) |
|
|
|
795 | (3) |
|
Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives |
|
|
798 | (1) |
|
Polyamides and Polyesters: Step-Growth Polymers |
|
|
799 | (3) |
|
Spectroscopy of Carboxylic Acid Derivatives |
|
|
802 | (19) |
|
Chemistry@Work: β-Lactam Antibiotics |
|
|
804 | (1) |
|
|
|
805 | (1) |
|
|
|
806 | (3) |
|
|
|
809 | (10) |
|
|
|
819 | (1) |
|
|
|
819 | (2) |
|
Carbonyl Alpha-Substitution Reactions |
|
|
|
|
|
821 | (3) |
|
Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions |
|
|
824 | (1) |
|
Alpha Halogenation of Aldehydes and Ketones |
|
|
824 | (3) |
|
Alpha Bromination of Carboxylic Acids: The Hell-Volhard-Zelinskii Reaction |
|
|
827 | (1) |
|
Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation |
|
|
828 | (4) |
|
Reactivity of Enolate Ions |
|
|
832 | (1) |
|
Halogenation of Enolate Ions: The Haloform Reaction |
|
|
833 | (1) |
|
Alkylation of Enolate Ions |
|
|
834 | (20) |
|
Chemistry@Work: Unusual Elements in Organic Chemistry |
|
|
842 | (2) |
|
|
|
844 | (1) |
|
|
|
844 | (2) |
|
|
|
846 | (7) |
|
|
|
853 | (1) |
|
|
|
853 | (1) |
|
Carbonyl Condensation Reactions |
|
|
|
Mechanism of Carbonyl Condensation Reactions |
|
|
854 | (1) |
|
Condensations of Aldehydes and Ketones: The Aldol Reaction |
|
|
855 | (3) |
|
Carbonyl Condensation Reactions versus Alpha-Substitution Reactions |
|
|
858 | (1) |
|
Dehydration of Aldol Products: Synthesis of Enones |
|
|
859 | (2) |
|
Using Aldol Reactions in Synthesis |
|
|
861 | (1) |
|
|
|
862 | (2) |
|
Intramolecular Aldol Reactions |
|
|
864 | (1) |
|
The Claisen Condensation Reaction |
|
|
865 | (2) |
|
Mixed Claisen Condensations |
|
|
867 | (2) |
|
Intramolecular Claisen Condensations: The Dieckmann Cyclization |
|
|
869 | (2) |
|
|
|
871 | (3) |
|
The Stork Enamine Reaction |
|
|
874 | (2) |
|
Carbonyl Condensation Reactions in Synthesis: The Robinson Annulation Reaction |
|
|
876 | (2) |
|
Biological Carbonyl Condensation Reactions |
|
|
878 | (14) |
|
Chemistry@Work: A Prologue to Metabolism |
|
|
878 | (2) |
|
|
|
880 | (1) |
|
|
|
881 | (2) |
|
|
|
883 | (8) |
|
|
|
891 | (1) |
|
|
|
891 | (1) |
|
|
|
|
|
|
892 | (3) |
|
Structure and Bonding in Amines |
|
|
895 | (1) |
|
Properties and Sources of Amines |
|
|
896 | (1) |
|
|
|
897 | (4) |
|
Basicity of Substituted Arylamines |
|
|
901 | (2) |
|
|
|
903 | (9) |
|
|
|
912 | (3) |
|
|
|
915 | (6) |
|
Tetraalkylammonium Salts as Phase-Transfer Catalysts |
|
|
921 | (2) |
|
|
|
923 | (20) |
|
Chemistry@Work: Opium and Opiates |
|
|
927 | (1) |
|
|
|
928 | (1) |
|
|
|
928 | (4) |
|
|
|
932 | (9) |
|
|
|
941 | (1) |
|
|
|
941 | (2) |
|
Biomolecules: Carbohydrates |
|
|
|
Classification of Carbohydrates |
|
|
943 | (1) |
|
Depicting Carbohydrate Stereochemistry: Fischer Projections |
|
|
944 | (4) |
|
|
|
948 | (1) |
|
Configurations of the Aldoses |
|
|
949 | (3) |
|
Cyclic Structures of Monosaccharides: Hemiacetal Formation |
|
|
952 | (2) |
|
Monosaccharide Anomers: Mutarotation |
|
|
954 | (2) |
|
Reactions of Monosaccharides |
|
|
956 | (7) |
|
Stereochemistry of Glucose: The Fischer Proof |
|
|
963 | (4) |
|
|
|
967 | (2) |
|
Polysaccharides and Their Synthesis |
|
|
969 | (3) |
|
Other Important Carbohydrates |
|
|
972 | (1) |
|
Cell-Surface Carbohydrates and Carbohydrate Vaccines |
|
|
973 | (13) |
|
Chemistry@Work: Sweetness |
|
|
975 | (1) |
|
|
|
976 | (1) |
|
|
|
977 | (1) |
|
|
|
978 | (6) |
|
|
|
984 | (1) |
|
|
|
984 | (2) |
|
Biomolecules: Amino Acids, Peptides, and Proteins |
|
|
|
Structures of Amino Acids |
|
|
986 | (5) |
|
|
|
991 | (3) |
|
|
|
994 | (2) |
|
Enantioselective Synthesis of Amino Acids |
|
|
996 | (2) |
|
|
|
998 | (1) |
|
Covalent Bonding in Peptides |
|
|
999 | (1) |
|
Structure Determination of Peptides: Amino Acid Analysis |
|
|
1000 | (1) |
|
Peptide Sequencing: The Edman Degradation |
|
|
1001 | (3) |
|
Peptide Sequencing: C-Terminal Residue Determination |
|
|
1004 | (1) |
|
|
|
1004 | (4) |
|
Automated Peptide Synthesis: The Merrifield Solid-Phase Technique |
|
|
1008 | (1) |
|
|
|
1009 | (1) |
|
|
|
1010 | (2) |
|
|
|
1012 | (2) |
|
How Do Enzymes Work? Citrate Synthase |
|
|
1014 | (2) |
|
|
|
1016 | (11) |
|
Chemistry@Work: Protein and Nutrition |
|
|
1016 | (1) |
|
|
|
1017 | (1) |
|
|
|
1018 | (2) |
|
|
|
1020 | (6) |
|
|
|
1026 | (1) |
|
|
|
1026 | (1) |
|
|
|
|
|
|
1027 | (3) |
|
|
|
1030 | (2) |
|
|
|
1032 | (1) |
|
|
|
1033 | (2) |
|
|
|
1035 | (3) |
|
Biosynthesis of Terpenoids |
|
|
1038 | (7) |
|
|
|
1045 | (2) |
|
Stereochemistry of Steroids |
|
|
1047 | (2) |
|
|
|
1049 | (12) |
|
Chemistry@Work: Cholesterol and Heart Disease |
|
|
1052 | (1) |
|
|
|
1053 | (1) |
|
|
|
1053 | (6) |
|
|
|
1059 | (1) |
|
|
|
1059 | (2) |
|
Biomolecules: Heterocycles and Nucleic Acids |
|
|
|
Five-Membered Unsaturated Heterocycles |
|
|
1061 | (1) |
|
Structures of Pyrrole, Furan, and Thiophene |
|
|
1062 | (1) |
|
Electrophilic Substitution Reactions of Pyrrole, Furan, and Thiophene |
|
|
1063 | (1) |
|
Pyridine, a Six-Membered Heterocycle |
|
|
1064 | (1) |
|
Electrophilic Substitution of Pyridine |
|
|
1065 | (1) |
|
Nucleophilic Substitution of Pyridine |
|
|
1066 | (1) |
|
|
|
1067 | (2) |
|
Nucleic Acids and Nucleotides |
|
|
1069 | (2) |
|
Structure of Nucleic Acids |
|
|
1071 | (1) |
|
Base Pairing in DNA: The Watson--Crick Model |
|
|
1072 | (2) |
|
Nucleic Acids and Heredity |
|
|
1074 | (1) |
|
|
|
1075 | (2) |
|
Structure and Synthesis of RNA: Transcription |
|
|
1077 | (1) |
|
RNA and Protein Biosynthesis: Translation |
|
|
1078 | (3) |
|
|
|
1081 | (2) |
|
|
|
1083 | (3) |
|
The Polymerase Chain Reaction |
|
|
1086 | (8) |
|
Chemistry@Work: DNA Fingerprinting |
|
|
1087 | (1) |
|
|
|
1088 | (1) |
|
|
|
1089 | (1) |
|
|
|
1090 | (3) |
|
|
|
1093 | (1) |
|
|
|
1093 | (1) |
|
The Organic Chemistry of Metabolic Pathways |
|
|
|
An Overview of Metabolism and Biochemical Energy |
|
|
1094 | (4) |
|
Catabolism of Fats: β-Oxidation |
|
|
1098 | (6) |
|
Catabolism of Carbohydrates: Glycolysis |
|
|
1104 | (6) |
|
The Conversion of Pyruvate to Acetyl CoA |
|
|
1110 | (3) |
|
|
|
1113 | (3) |
|
Catabolism of Proteins: Transamination |
|
|
1116 | (2) |
|
|
|
1118 | (4) |
|
Carbohydrate Biosynthesis: Gluconeogenesis |
|
|
1122 | (3) |
|
Some Conclusions About Biological Chemistry |
|
|
1125 | (9) |
|
Chemistry@Work: Basal Metabolism |
|
|
1126 | (1) |
|
|
|
1126 | (1) |
|
|
|
1127 | (6) |
|
|
|
1133 | (1) |
|
|
|
1133 | (1) |
|
Orbitals and Organic Chemistry: Pericyclic Reactions |
|
|
|
Molecular Orbitals of Conjugated π Systems |
|
|
1134 | (1) |
|
Molecular Orbitals and Pericyclic Reactions |
|
|
1135 | (2) |
|
|
|
1137 | (2) |
|
Stereochemistry of Thermal Electrocyclic Reactions |
|
|
1139 | (2) |
|
Photochemical Electrocyclic Reactions |
|
|
1141 | (1) |
|
|
|
1142 | (2) |
|
Stereochemistry of Cycloadditions |
|
|
1144 | (2) |
|
Sigmatropic Rearrangements |
|
|
1146 | (2) |
|
Some Examples of Sigmatropic Rearrangements |
|
|
1148 | (2) |
|
A Summary of Rules for Pericyclic Reactions |
|
|
1150 | (10) |
|
Chemistry@Work: Vitamin D, the Sunshine Vitamin |
|
|
1151 | (1) |
|
|
|
1152 | (1) |
|
|
|
1152 | (6) |
|
|
|
1158 | (1) |
|
|
|
1158 | (2) |
|
|
|
|
|
|
1160 | (1) |
|
Stereochemistry of Polymerization: Ziegler--Natta Catalysts |
|
|
1161 | (2) |
|
|
|
1163 | (2) |
|
|
|
1165 | (2) |
|
Polymer Structure and Physical Properties |
|
|
1167 | |
|
Chemistry@Work: Biodegradable Polymers |
|
|
1170 | (2) |
|
|
|
1172 | (1) |
|
|
|
1172 | (4) |
|
|
|
1176 | (1) |
|
|
|
1176 | |
| Appendix A: Nomenclature of Polyfunctional Organic Compounds |
|
1 | (6) |
| Appendix B: Acidity Constants for Some Organic Compounds |
|
7 | (2) |
| Appendix C: Glossary |
|
9 | (22) |
| Appendix D: Answers to Selected In-Text Problems |
|
31 | |
| Index |
|
1 | |