Freshman Organic Chemistry 2
By J. Michael McBride
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Description
This is a continuation of Freshman Organic Chemistry I (CHEM 125a), the introductory course on current theories of structure and mechanism in organic chemistry for students with excellent preparation in chemistry and physics. This semester treats simple and complex reaction mechanisms, spectroscopy, organic synthesis, and some molecules of nature.
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1. Mechanism: How Energies and Kinetic Order Influence Reaction Rates | This second semester of Freshman Organic Chemistry builds on the first semester’s treatment of molecular structure and energy* to discuss how reaction mechanisms have been discovered and understood. | 4/2/2012 | Free | View in iTunes |
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2. Peculiar Rate Laws, Bond Dissociation Energies, and Relative Reactivities | Curious kinetic orders can be mechanistically informative. Fractional kinetic orders suggest dissociation of a dominant aggregate to give a smaller reactive species. | 4/2/2012 | Free | View in iTunes |
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3. Rate and Selectivity in Radical-Chain Reactions | The reactivity-selectivity principle explains why bromine atoms are more selective that chlorine atoms in abstracting hydrogen atoms from carbon. | 4/2/2012 | Free | View in iTunes |
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4. Electronegativity, Bond Strength, Electrostatics, and Non-Bonded Interactions | A student provides insight on fractional-order rate laws. Bonds involving atoms with lone-pair electrons are weakened by electron-pair repulsion. | 4/2/2012 | Free | View in iTunes |
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5. Solvation, H-Bonding, and Ionophores | Most organic reactions occur in solution, and particularly in the case of ions, one must consider non-bonded interactions with neighboring molecules. | 4/2/2012 | Free | View in iTunes |
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6. Brønsted Acidity and the Generality of Nucleophilic Substitution | The coincidentally substantial extent of ionic dissociation of water provides an example of Brønsted acidity, or nucleophilic substitution at hydrogen. | 4/2/2012 | Free | View in iTunes |
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7. Nucleophilic Substitution Tools - Stereochemistry, Rate Law, Substrate, Nucleophile, Leaving Group | SN2 substitution provides an example of establishing the mechanism of a chemical reaction by disproving all the alternatives. | 4/2/2012 | Free | View in iTunes |
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8. Solvent, Leaving Group, Bridgehead Substitution, and Pentavalent Carbon | The nature of nucleophiles and leaving groups has strong influence on the rate of SN2 reactions. | 4/2/2012 | Free | View in iTunes |
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9. Pentavalent Carbon? E2, SN1, E1 | Preliminary X-ray analysis of molecules that have been designed to favor a carbon with five bonds seemed to suggest the possibility of a pentavalent intermediate in SN2 reactions, but further analysis of these structures showed just the opposite. | 4/2/2012 | Free | View in iTunes |
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10. Cation Intermediates. Alkenes: Formation, Addition, and Stability | Bridged pentavalent carbon structures can be intermediates or transition states of cation rearrangement during SN1 reactions, and short-lived ion pairs explain net stereochemical inversion. | 4/2/2012 | Free | View in iTunes |
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11. Carbocations and the Mechanism of Electrophilic Addition to Alkenes and Alkynes | Substition stabilizes alkenes, and addition of acids is thermodynamically favorable in acidic media. | 4/2/2012 | Free | View in iTunes |
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12. Nucleophilic Participation During Electrophilic Addition to Alkenes: Halogen, Carbene, and Borane | When electrophilic addition involves a localized carbocation intermediate, skeletal rearrangement sometimes occurs. | 4/2/2012 | Free | View in iTunes |
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13. Addition to Form Three-Membered Rings: Carbenoids and Epoxidation | After drill on the mechanism of the pinacol rearrangement, this lecture applies molecular-orbital analysis to simultaneous electrophilic/nucleophilic attack by a single atom to form a three-membered ring from an alkene. | 4/2/2012 | Free | View in iTunes |
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14. Epoxide Opening, Dipolar Cycloaddition, and Ozonolysis | The formation of epoxides and the regiospecificity of their acid- and base-catalyzed ring openings underlines the importance of thinking carefully. | 4/2/2012 | Free | View in iTunes |
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15. Metals and Catalysis in Alkene Oxidation, Hydrogenation, Metathesis, and Polymerization | Alkenes may be oxidized to diols by permanganate or by OsO4 catalysis. Metal catalysts provide orbitals that allow simultaneous formation of two bonds from metal to alkene or H2. | 4/2/2012 | Free | View in iTunes |
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16. Isoprenoids, Rubber, and Tuning Polymer Properties | Isoprenoid or terpene natural products, that seem to be made from isoprene (2-methylbutadiene), are formed by oligomerization of electrophilic isopentenyl pyrophosphate (IPP). | 4/2/2012 | Free | View in iTunes |
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17. Alkynes. Conjugation in Allylic Intermediates and Dienes | Because of their unusual acidity very strong base makes it possible to isomerize an internal acetylene to the less stable terminal isomer. | 4/2/2012 | Free | View in iTunes |
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18. Linear and Cyclic Conjugation Theory. 4n+2 Aromaticity | Despite the substantial change in the energy of individual orbitals, the overall pi-electron energy and orbital shape changes little upon linear conjugation of two double bonds. | 4/2/2012 | Free | View in iTunes |
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19. Aromatic Transition States: Cycloaddition and Electrocyclic Reactions | Cyclic conjugation that arises when p-orbitals touch one another can be as important for transition states as aromaticity is for stable molecules. It is the controlling factor in “pericyclic” reactions. | 4/2/2012 | Free | View in iTunes |
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20. Electronic and Vibrational Spectroscopy | Time-dependent quantum mechanics shows how mixing orbitals of different energy causes electrons to vibrate. | 4/2/2012 | Free | View in iTunes |
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21. Functional Groups and Fingerprints in IR Spectroscopy. Precession of Magnetic Nuclei | Infrared spectroscopy provides information for analyzing molecular structure and for understanding bonding and dynamics. | 4/2/2012 | Free | View in iTunes |
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22. Medical MRI and Chemical NMR | Magnetic resonance imaging (MRI) requires gradients in the applied magnetic field, while chemical nuclear magnetic resonance (NMR) requires a highly uniform field. | 4/2/2012 | Free | View in iTunes |
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23. Diamagnetic Anisotropy and Spin-Spin Splitting | Through-space interaction between magnets of fixed strength and orientation averages to zero during random molecular tumbling, suggesting that the local field about a proton should be sensitive only to electrons that orbit about itself. | 4/2/2012 | Free | View in iTunes |
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24. Higher-Order Effects, Dynamics, and the NMR Time Scale | Because spin-spin splitting depends on electron spin precisely at a nucleus, splitting by a C-13 depends on its orbital’s hybridization. | 4/2/2012 | Free | View in iTunes |
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25. C-13 and 2D NMR. Electrophilic Aromatic Substitution | Proton decoupling simplifies C-13 NMR spectra. Dilute double labeling with C-13 confirmed the complex rearrangement scheme in steroid biosynthesis. | 4/2/2012 | Free | View in iTunes |
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26. Aromatic Substitution in Synthesis: Friedel-Crafts and Moses Gomberg | The Friedel-Crafts reaction creates new alkyl- or acyl-aromatic bonds, with or without cation rearrangement. | 4/2/2012 | Free | View in iTunes |
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27. Triphenylmethyl and an Introduction to Carbonyl Chemistry | Painstaking studies of his “hexaphenylethane” and its reactivity convinced Gomberg that he had prepared the first trivalent carbon compound, triphenylmethyl radical, the discovery of which marked the emergence of fundamental organic chemistry in Ame | 4/2/2012 | Free | View in iTunes |
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28. Mechanism and Equilibrium of Carbonyl Reactions | This lecture aims at developing facility with devising plausible mechanisms for acid- and base-catalyzed reactions of carbonyl compounds, carboxylic acids, and their derivatives. | 4/2/2012 | Free | View in iTunes |
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29. Imines and Enamines. Oxidation and Reduction | Imines are pervasive in chemistry and biology, playing key roles both the in artificial Strecker synthesis of amino acids and their biosynthesis by L-glutamate dehydrogenase and by transamination. | 4/2/2012 | Free | View in iTunes |
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30. Oxidation States and Mechanisms | A difficult exam question shows how visible and NMR spectroscopy related to long-term misassignment of the structure for the triphenylmethyl dimer. | 4/2/2012 | Free | View in iTunes |
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31. Periodate Cleavage, Retrosynthesis, and Green Chemistry | The ability of periodic acid (HIO4) to cleave the C-C bond of vicinal diols and [gr]α-hydroxycarbonyl compounds allowed structure determination of sugars and their ketals before spectroscopy was available. | 4/2/2012 | Free | View in iTunes |
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32. Measuring Bond Energies: Guest Lecture by Prof. G. Barney Ellison | Spectroscopic determination of bond dissociation energies is relatively straightforward for many diatomic molecules, but for polyatomic molecules it requires merging the results from a variety of challenging experiments. | 4/2/2012 | Free | View in iTunes |
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33. Green Chemistry. Acids and Acid Derivatives | Green chemistry needs new asymmetric reactions and safer, more environmental Mitsunobu reactions. The Mitsunobu mechanism is general and reliable, but atom inefficient, generating almost 30 times as much weight of by-products. | 4/2/2012 | Free | View in iTunes |
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34. Acids and Acid Derivatives | Reactions of carboxylic acids and their salts include nucleophilic substitution and decarboxylation to leave enols, free radicals, or alkyl halides. | 4/2/2012 | Free | View in iTunes |
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35. Acyl Insertions and [gr]α-Reactivity | When a nucleophilic atom bearing a good leaving group attacks a carbonyl group, an adjacent R group can migrate to the new atom, inserting it into the R-acyl bond. | 4/2/2012 | Free | View in iTunes |
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36. [gr]α-Reactivity and Condensation Reactions | As in many synthetic procedures, an important challenge in ketone alkylation is choosing reagents and conditions that allow control of isomerism and of single vs. multiple substitution. | 4/2/2012 | Free | View in iTunes |
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37. Proving the Configuration of Glucose and Synthesizing Two Unnatural Products | Modern spectroscopic tools show not only the constitution, configuration, and conformation of glucose but also how it interconverts between isomeric hemiketal pyranose rings. | 4/2/2012 | Free | View in iTunes |
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38. Review: Synthesis of Cortisone | Discoverers of the structure and biological activity of steroid hormones won seven Nobel Prizes between 1927 and 1975. The course ends with thanks to those, young and old, who have taught us all. | 4/2/2012 | Free | View in iTunes |
| 38 Items |
Customer Reviews
Freshman Organic Chemistry 2
Where is Freshman Organic Chemistry 1? I'd like to start at the beginning.
I also cannot find that first course
Where is freshman chemistry 1
