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Chemistry 110A Exam 4 Review Sheet Review Session: Wednesday, November 2, 7:00 PM, SN 111 Exam 4: Friday, November 4, 7:50 AM, SN Aud Chapter 8 1. Be able to explain the addition of HX to alkenes and alkynes as a regioselective reaction, and be able to employ an arrow-pushing mechanism to explain how this reaction proceeds. 2. Be able to write a definition of Markovnikov’s rule, and employ the Hammond-Leffler postulate in an explanation of the regioselective addition of HX to an unsymmetrical alkene. 3. Be able to explain how alkenes can be hydrated with water under acidic conditions, using an arrow-pushing mechanism to explain how the reaction works. a. Be able to explain the differences between this reaction and the reverse process, i.e., the acid-catalyzed dehydration of alcohols to form alkenes. 4. Be able to explain how alkenes can be hydrated in a Markovnikov fashion using oxymercuration-demercuration, using an arrow-pushing mechanism for first step of this process. 5. Be able to explain how alkenes can be hydrated in an anti-Markovnikov fashion using hydroboration-oxidation, using an arrow pushing mechanism for the entirety of the process. Be able to incorporate structural features into your example so that you can explain the stereochemistry of addition/oxidation. 6. Be able to explain the regio and stereospecific addition of Br2 and Cl2 to alkenes and alkynes, using an arrow-pushing mechanism to explain how this reaction works. 7. Be able to explain the regio and stereospecific addition of Br2/H2O and Cl2/H2O to alkenes and alkynes (the halohydrin reaction), using an arrow-pushing mechanism to explain how this reaction works. 8. Be able to explain the reactions of carbenes with alkenes, using an arrow-pushing mechanism [with the exception of 8c] to explain how these reactions work, starting from: a. A base-induced alpha-elmination of chloroform. b. Diazomethane. c. The Simmons-Smith reagent. 9. Be able to explain how OsO4 or KMnO4 can be used with variable success to syndihydroxylate alkenes, using an arrow-pushing mechanism to explain how the addition step of these reactions work. a. Be able to qualitatively explain how OsO4 can be used in a catalytic manner, i.e., the Upjohn process. 10. Be able to write down the cleavage products of alkenes and alkynes when treated with hot KMnO4 or O3. a. Be able to use these reactions in syntheses and to degrade molecules in order to determine their structure. 11. You should be able to predict the products of these reactions and be able to incorporate any of these into a synthesis of a small organic compound. Chapter 9 1. Be able to explain the physical basis of NMR spectroscopy in terms of spins, energy levels, a magnetic field, and radiowaves. 2. Be able to explain the origin of factors affecting the chemical shift, such as diamagnetic shielding, electronegativity, and ring current effects. 3. Be able to use the Beer’s Law aspect of NMR spectroscopy to quantify NMR signal integrals in 1H spectroscopy as arising from integral numbers of hydrogen atoms. 4. Be able to explain the qualitative origin of spin-spin “J” coupling in NMR spectra, the ‘n+1 rule, and how this rule can be used to establish fragment structures. 5. Be able to qualitatively describe how a rapid molecular process (conformational interchange, proton exchange) leads to averaging in NMR spectra. 6. Be able to assign groups in molecules as enantiotopic, homotopic, diastereotopic, and heterotopic, and be able to predict how these designations will manifest themselves in NMR spectra 7. Be able to explain why 13C spectra consist of single peaks for each carbon atom, and why these spectra are much noisier than 1H spectra. 8. Be able to explain how mass spectrometry works and how it can be used to determine a molecular weight and molecular formula for small organic molecules. 9. Be able to assign a chemical structure that is consistent with mass spectral, 1H, and 13C NMR data, or vice-versa.