The Molecular Modeling Workbook for ORGANIC CHEMISTRY

Автор(ы):Hehre J. Warren
06.10.2007
Год изд.:1998
Описание: This workbook contains over 200 problems that will allow you to build and refine your understanding of chemistry from the molecule's "eye view". This is achieved by basing every problem on a set of molecular models that you view and manipulate on your own personal computer. The authors believe that this combination of problems+models will improve everybody understanding of molecular structure and the relationship between molecular structure and other properties. More importantly, they believe that when students do the problems in this workbook they will gain a much better grasp of the conceptual basis of organic chemistry, and that this will make the rest of they study of organic chemistry more satisfactory and ultimately more successful.
Оглавление:
The Molecular Modeling Workbook for ORGANIC CHEMISTRY — обложка книги.
To the Student  [1]
To the Teacher  [3]
How to Use SpARTANView  [5]
How to Use Energies to Calculate Thermodynamic and Kinetic Data  [13]
Molecular Orbitals. Quantum Mechanics in Pictures  [15]
Electron Densities and the Sizes and Shapes of Molecules  [23]
Electrostatic Potential Maps and Molecular Charge Distributions  [29]
Chapter 1 Lewis Structures and Resonance Theory  [33]
Chapter 2 Acids and Bases  [47]
Chapters Reaction Pathways and Mechanisms  [59]
Chapter 4 Stereochemistry  [67]
Chapter 5 Alkanes and Cycloalkanes  [73]
Chapter 6 Nucleophilic Substitution and Elimination  [85]
Chapter 7 Alkenes andAlkynes  [101]
Chapter 8 Alcohols and Ethers  [119]
Chapter 9 Ketones and Aldehydes. Nucleophilic Addition  [133]
Chapter 10 Carboxylic Acid Derivatives. Nucleophilic Substitution  [147]
Chapter 11 Enolates as Nucleophiles  [159]
Chapter 12 Conjugated Polyenes and Aromaticity  [173]
Chapter 13 Electrophilic and Nucleophilic Aromatic Substitution  [185]
Chapter 14 Nitrogen-Containing Compounds  [199]
Chapter 15 Heterocycles  [211]
Chapter 16 Biological Chemistry  [219]
Chapter 17 Free Radicals andCarbenes  [235]
Chapter 18 Polymers  [247]
Chapter 19 Spectroscopy  [253]
Chapter 20 Mass Spectrometry  [267]
Chapter 21 Pericyclic Reactions  [271]
Appendix A Common Terms and Acronyms  [281]
Appendix В Models on the CD-ROM  [285]
Appendix С Making New Models  [287]
Index  [289]
Index of Molecules  [295]
Index of Transition States  [305]
Index of Reaction Sequences  [307]

To the Student  [1]
To the Teacher  [3]
How to Use SpARTANView  [5]
How to Use Energies to Calculate Thermodynaniic and Kinetic Data  [13]
Molecular Orbitals. Quantum Mechanics in Pictures  [15]
Electron Densities and the Sizes and Shapes of Molecules  [23]
Electrostatic Potential Maps and Molecular Charge Distributions  [29]
Chapter 1 Lewis Structures and Resonance Theory  [33]
  1.1 Are All Chemical Bonds the Same?  [34]
  1.2 Bond Lengths in Hydrocarbons  [35]
  1.3 Dipole Moments and Molecular Polarity  [36]
  1.4 Chromatography and Molecular Polarity  [37]
  1.5 Formal Charges vs. Atomic Charges  [38]
  1.6 Resonance Structures. The Sum of the Parts  [39]
  1.7 Resonance Energy  [40]
  1.8 Azide  [41]
  1.9 Molecular Geometry and the Number of Electrons  [42]
  1.10 Too Many Electrons. Lone Pairs  [43]
  1.11 Too Few Electrons. Multicenter Bonding  [44]
  1.12 Localized vs. Delocalized Charge  [45]
Chapter 2 Acids and Bases  [47]
  2.1 Liquid Water  [48]
  2.2 Structure of Hydrogen-Bonded Complexes  [49]
  2.3 What is Hydronium?  [50]
  2.4 Acid-Base Properties and Partial Charge  [51]
  2.5 Acid-Base Properties and Charge Delocalization. I  [52]
  2.6 Acid-Base Properties and Charge Delocalization. II  [53]
  2.7 Acid-Base Properties and lon-Dipole Interactions  [54]
  2.8 Alkyl = H. Fact or Fiction?  [55]
  2.9 Acid Dissociation in the Gas Phase and in Water  [56]
  2.10 Long-Range Substituent Effects  [57]
Chapter 3 Reaction Pathways and Mechanisms  [59]
  3.1 Reaction Energy Diagrams  [60]
  3.2 What Do Transition States Look Like?  [61]
  3.3 Electronic Structure of Transition States  [62]
  3.4 Mechanistic Families  [63]
  3.5 Selectivity in Exothermic Reactions  [64]
  3.6 Selectivity in Endothermic Reactions  [65]
Chapter 4 Stereochemistry  [67]
  4.1 Enantiomers  [68]
  4.2 Diastereomers vs. Conformers  [69]
  4.3 Chiral Molecules without Chiral Centers  [70]
  4.4 Configuration Inversion  [71]
Chapter 5 Alkanes and Cycloalkanes  [73]
  5.1 Eclipsed vs. Staggered. Tetrahedral Carbons  [74]
  5.2 Eclipsed vs. Staggered. Trigonal Carbons  [75]
  5.3 Steric Control of Alkane Conformation  [76]
  5.4 Ring Conformation  [77]
  5.5 Steric Control of Ring Conformation. I  [78]
  5.6 StericControl of Ring Conformation. II  [79]
  5.7 Electronic Control of Ring Conformation  [80]
  5.8 Mechanism of Ring Inversion  [81]
  5.9 Fused Rings  [82]
  5.10 Ring Strain  [83]
Chapter 6 Nucleophilic Substitution and Elimination  [85]
  6.1 S(?)2 and Proton-Transfer Reactions  [86]
  6.2 S(?)2 Nucleophiles  [87]
  6.3 Ambident S(?)2 Nucleophiles  [88]
  6.4 Stereochemistry of S(?)2 Reactions  [89]
  6.5 Steric Hindrance of S(?)2 Reactions  [90]
  6.6 S(?)1 Reaction of AlkyIHalides and Water  [91]
  6.7 Acid-Catalyzed S(?)1 Reactions  [92]
  6.8 Stability of Carbocation Intermediates  [93]
  6.9 Resonance-Assisted S(?)1 Reactions  [94]
  6.10 Strain Effects on S(?)1 Reaction Rates  [95]
  6.11 Stereochemistry of S(?)1 Reactions  [96]
  6.12 Phenyl vs. Benzyl Cation  [97]
  6.13 Solvent Effects on S(?)1 Reaction Rates  [98]
  6.14 Stereochemistry of E2 Elimination  [99]
  6.15 Conformational Control of E2 Elimination  [100]
Chapter 7 Alkenes and Alkynes  [101]
  7.1 cis-trans Isomerization  [102]
  7.2 Electrophilic Addition to Alkenes  [103]
  7.3 Alkene Reactivity toward Electrophiles  [104]
  7.4 Electrophilic Addition to Strained Alkenes  [105]
  7.5 trans Cycloalkenes  [106]
  7.6 Stereochemistry of Electrophilic Additions  [107]
  7.7 Regiochemistry of Electrophilic Additions  [108]
  7.8 Hyperconjugation  [109]
  7.9 Skeletal Rearrangements of Carbocation Intermediates  [110]
  7.10 Electrophilic Addition of Br(?) to Alkenes  [111]
  7.11 Hydroboration of Alkenes  [112]
  7.12 Regioselectivity in Hydroboration of Alkenes  [113]
  7.13 Stereochemistry of Alkene Hydrogenation  [114]
  7.14 Alkyne vs. Alkene Reactivity  [115]
  7.15 Electrophilic Additions to Alkynes. Vinyl Cations  [116]
  7.16 Hydrogenation of Alkynes  [117]
  7.17 Anions from Alkynes  [118]
Chapter 8 Alcohols and Ethers  [119]
  8.1 Hydrogen Bonding in Alcohols  [120]
  8.2 Conformations of 1,2-Ethanediol  [121]
  8.3 pK(?)'s of Alcohols  [122]
  8.4 Metal Hydrides vs. Hydrogen Halides  [123]
  8.5 Alkoxides. Bases or Nucleophiles?  [124]
  8.6 Thionyl Chloride and Phosphorus Trichloride  [125]
  8.7 Activating Oxygen as a Leaving Group  [126]
  8.8 Cleavage of an Unsymmetric Ether  [127]
  8.9 The Pinacol Rearrangement  [128]
  8.10 Stereoselectivity of Epoxide Ring Opening  [129]
  8.11 Regioselectivity of Epoxide Ring Opening  [130]
  8.12 Crown Ethers  [131]
Chapter 9 Ketones and Aldehydes. Nucleophilic Addition  [133]
  9.1 Formaldehyde  [134]
  9.2 Carbonyl Hydration  [135]
  9.3 Non-Existent Alcohols  [136]
  9.4 Carbonyl Basicity  [137]
  9.5 Selective Formation of Ketals  [138]
  9.6 Cyanohydrin Formation  [139]
  9.7 Hydride Reducing Agents  [140]
  9.8 Grignard Reagents  [141]
  9.9 Stereochemistry of Nucleophilic Additions. Methylcyclohexanone  [142]
  9.10 Michael Addition  [143]
  9.11 Phosphorus Ylides  [144]
  9.12 Sulfur Ylides  [145]
Chapter 10 Carboxylic Acid Derivatives. Nucleophilic Substitution  [147]
  10.1 Conformational Properties of Carboxylic Acids and Ami des  [148]
  10.2 Electrophilic Properties of Carboxylic Acid Derivatives  [149]
  10.3 Acid Cleavage of Esters, Amides and Nitriles  [150]
  10.4 Esters vs. Anhydrides  [151]
  10.5 Esters vs. Thioesters  [152]
  10.6 Amides vs. Ureas  [153]
  10.7 Ketene  [154]
  10.8 Penicillin  [155]
  10.9 Intra and Intermolecular Hydrogen Bonding  [156]
  10.10 Fatty Acid and Fats. What Makes Good Soap?  [157]
Chapter 11 Enolates as Nucleophiles  [159]
  11.1 Keto/Enol Tautomerism  [160]
  11.2 H/D Exchange Reactions  [161]
  11.3 What Makes a Good Enolate?  [162]
  11.4 Enolate Acidity, Stability and Geometry  [163]
  11.5 Kinetic Enolates  [164]
  11.6 Real Enolates  [165]
  11.7 Enolates, Enols andEnamines  [166]
  11.8 Enolates are Ambident Nucleophiles  [167]
  11.9 Silylation of Enolates  [168]
  11.10 Stereochemistry of Enolate Alkylation  [169]
  11.11 Enolate Dianions  [170]
  11.12 Aldol Condensation  [171]
  11.13 Dieckmann Condensation  [172]
Chapter 12 Conjugated Polyenes and Aromaticity  [173]
  12.1 Conjugated Polyenes  [174]
  12.2 Resonance Control of Conformation  [175]
  12.3 1,2 vs. 1,4 Addition  [176]
  12.4 Benzene or 1,3,5-Cyclohexatriene? Interpretation of Resonance Structures  [177]
  12.5 Addition Reactions involving Aromatic Rings  [178]
  12.6 Does Resonance Always Stabilize a Molecule?  [179]
  12.7 Huckel's Rule. Cyclooctatetraene  [180]
  12.8 Polar Hydrocarbons  [181]
  12.9 Does Resonance Always Stabilize a Cation?  [182]
  12.10 Does Resonance Always Stabilize an Anion?  [183]
  12.11 Metal-Bonded Cyclopentadienyl Anions  [184]
Chapter 13 Electrophilic and Nucleophilic Aromatic Substitution  [185]
  13.1 Addition vs. Substitution  [186]
  13.2 Electrophilic Bromination of Benzene  [187]
  13.3 Useful Electrophiles  [188]
  13.4 Directing Effects on Electrophilic Nitration  [189]
  13.5 Activating/Deactivating Effects on Electrophilic Aromatic Substitution  [190]
  13.6 Electrophilic Aromatic Substitution in Polysubstituted Benzenes  [191]
  13.7 Electrophilic Aromatic Substitution in Biphenyls  [192]
  13.8 Electrophilic Aromatic Substitution in Naphthalene  [193]
  13.9 Electrophilic Aromatic Substitution in Ferrocene  [194]
  13.10 Nucleophilic Aromatic Substitution. Addition-Elimination  [195]
  13.11 Substituent Effects on Nucleophilic Aromatic Substitution  [196]
  13.12 Nucleophilic Aromatic Substitution. Benzyne  [197]
Chapter 14 Nitrogen-Containing Compounds  [199]
  14.1 Pyramidal Inversion in Ammonia  [200]
  14.2 Conformations of Hydrazine and Hydrogen Peroxide  [201]
  14.3 Ammonia or Trimethylamine. Which is the Stronger Base  [202]
  14.4 Push-Pull Resonance. The Basicity of para-Nitroaniline  [203]
  14.5 Amine Nucleophiles  [204]
  14.6 Amines or Amides. Which are Better Nucleophiles?  [205]
  14.7 Gabriel Amine Synthesis  [206]
  14.8 Phase-Transfer Catalysis  [207]
  14.9 Diazonium Ions  [208]
  14.10 Aryl Diazonium Ions  [209]
  14.11 Azo Dyes  [210]
Chapter 15 Heterocycles  [211]
  15.1 Imidazole and Pyrazole. Where is the Basic Site?  [212]
  15.2 Pyrrole  [213]
  15.3 Nucleophilicity of Benzene and Pyridine  [214]
  15.4 Electrophilic Substitution of Thiophenes  [215]
  15.5 Electrophilic Substitution of Indoles  [216]
  15.6 Tautomers of Hydroxypyridine and Hydroxypyrimidine  [217]
  15.7 Porphyrins  [218]
Chapter 16 Biological Chemistry  [219]
  16.1 Vitamin C. Ascorbic Acid  [220]
  16.2 Vitamin E  [221]
  16.3 Glucose. I  [222]
  16.4 Glucose. II  [223]
  16.5 Structure of Glycine in the Gas Phase and in Water  [224]
  16.6 Amino Acid Sidechains  [225]
  16.7 Amino Acid Conformation  [226]
  16.8 Amide Bonds  [227]
  16.9 Structure of Polypeptides  [228]
  16.10 Nutrasweet  [229]
  16.11 DNA Base Pairs  [230]
  16.12 Tautomers of Nucleotide Bases  [231]
  16.13 Structure of the Double Helix  [232]
  16.14 Photosynthesis  [233]
Chapter 17 Free Radicals and Carbenes  [235]
  17.1 Structure of Free Radicals  [236]
  17.2 CH Bond Energies in Hydrocarbons  [237]
  17.3 Free Radical Chlorination of Alkanes  [238]
  17.4 Chlorination of Toluene  [239]
  17.5 Radical Initiators  [240]
  17.6 Free Radicals Add to Double Bonds  [241]
  17.7 Spin Traps and Radical Scavengers  [242]
  17.8 Singlet and Triplet Methylene  [243]
  17.9 Sources of Methylene  [244]
  17.10 Carbenes Add to Alkenes  [245]
Chapter 18 Polymers  [247]
  18.1 Nylon  [248]
  18.2 Synthetic Polymers  [249]
  18.3 Rubber  [250]
  18.4 Alkene Polymerization  [251]
  18.5 Stereoregularity of Polypropylene  [252]
Chapter 19 Spectroscopy  [253]
  19.1 Vibrational Spectrum of Water  [254]
  19.2 Infrared Spectra of Carbonyl Compounds  [255]
  19.3 Concentration Effects on Infrared Spectra  [256]
  19.4 Vibrational Spectrum of 1-Octyne  [257]
  19.5 Spectral Identification of Short-Lived Molecules  [258]
  19.6 Electronic Spectra of Conjugated Alkenes  [259]
  19.7 Solvent Effects on Electronic Spectra  [260]
  19.8 Singlet and Triplet Anthrone  [261]
  19.9 Magnetic Anistropy and Chemical Shifts  [262]
  19.10 Vicinal H-H Coupling and the Karplus Equation  [263]
  19.11 Long-Range "W" Coupling  [264]
  19.12 Substituent Effects on (?)C Chemical Shifts  [265]
Chapter 20 Mass Spectrometry  [267]
  20.1 Mass Spectra of Alcohols  [268]
  20.2 Mass Spectra of Alkenes and Arenes. Resonance Stabilized Cations  [269]
  20.3 McLafferty Rearrangement  [270]
Chapter 21 Pericyclic Reactions  [271]
  21.1 Electrocyclic Reactions  [272]
  21.2 The Diels-Alder Reaction. A Symmetry Allowed Process  [273]
  21.3 Electron-Flow in Diels-Alder Reactions  [274]
  21.4 Catalysis of Diels-Alder Reactions  [275]
  21.5 Stereochemistry of Diels-Alder Reactions. Thermodynamic vs. Kinetic Control  [276]
  21.6 Effect of Conformation on Rates of Diels-Alder Reactions  [277]
  21.7 Cope and Claisen Rearrangements  [278]
  21.8 Ene Reaction. Kinetic Isotope Effects  [279]
Appendix A Common Terms and Acronyms  [281]
Appendix В Models on the CD-ROM  [285]
Appendix С Making New Models  [287]
Index  [289]
Index of Molecules  [295]
Index of Transition States  [305]
Index of Reaction Sequences  [307]
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