CHEM& 261: Organic Chemistry I

In Brief:

1. Pertinent general chemistry review: molecular orbital theory, orbital hybridization, molecular orbital theory, molecular structure/geometry, electronegativity & polarity, acid/base theory
2. Overview of organic functional groups
3. Alkanes and cycloalkanes: Sources and separation, nomenclature, conformational analysis, chemical reactions
4. Stereochemistry: chiral molecules, stereospecific and stereoselective reactions, determining enantiomeric excess, prochiral molecules
5. Nucleophilic Substitution Reactions: Sn1 vs. Sn2 and conditions favoring each; stereochemical and kinetic considerations
6. Elimination Reactions: E1 vs. E2 and conditions favoring each; stereochemical and kinetic considerations
7. Alkenes and Alkynes: Structure, nomenclature, properties, reactions, synthesis
8. Fundamental Laboratory Techniques
9. Analytical techniques: infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectrometry

In Detail:

1. Discuss covalent bonding from the perspectives of Lewis theory, valence bond theory, and molecular orbital theory
2. List the properties of carbon that enable it to be the fundamental atom in organic chemistry.
3. Identify constitutional isomers.
4. Review polarity in covalent systems and the implications for physical properties and reactivities in organic functional groups
5. Describe the different types of intermolecular interactions, their relative strengths, and recognize when they are occurring.
6. Identify the common organic functional groups.
7. Explain the theoretical basis of infrared spectroscopy.
8. Identify molecules based on their infrared spectra.
9. Analyze acid/base reactions from the perspectives of Brønsted-Lowry and Lewis theory.
10. Develop a working understanding of the concept of resonance
11. Discuss the dependence of acid/base strength on molecular structure, and rationalize the relative pKa values of important structural motifs in organic chemistry.
12. Apply fundamental thermodynamic principles to organic chemical reactions.
13. Apply fundamental kinetics principles to organic chemical reactions.
14. Name alkanes, alkenes, alkynes, alkyl halides, and alcohols according to IUPAC rules.
15. Explain the physical properties of the hydrocarbons.
16. Discuss the different conformational possibilities for the alkanes and cycloalkanes.
17. Identify cis/trans isomers in the context of cycloalkanes and alkenes.
18. Write equations for the fundamental reactions of alkanes.
19. Write equations for the synthesis of alkanes.
20. Discuss the difference between stereoisomerism and constitutional isomerism.
21. Discuss the difference between diastereoisomerism and enantiomerism.
22. Discuss the origin of molecular chirality.
23. Name chiral molecules according to IUPAC rules (RS and EZ systems as applicable).
24. Explain the ability of some molecules to rotate the plane of plane-polarized light.
25. Draw three-dimensional representations of organic molecules.
26. Explain how molecular configurations are determined and how racemic mixtures are resolved.
27. Define and determine enantiomeric excess
28. Define prochirality and discuss the implications of homotopic, enantiotopic, and diastereotopic positions in 3 dimensionally discriminating analytical and biological environments
29. Write detailed reaction mechanisms for SN2 and SN1 reactions.
30. Analyze the kinetics and stereochemistry of both SN2 and SN1 reactions.
31. Explain the relative stabilities of carbocations.
32. Discuss major considerations for the use of nucleophilic substitution reactions in synthesis.
33. Write detailed reaction mechanisms for E2 and E1 reactions.
34. Analyze the kinetics and stereochemistry of both E2 and E1 reactions.
35. Predict when a reaction is likely to proceed via the SN2, SN1, E2, or E1 mechanism.
36. Explain the relative stabilities of alkenes.
37. Propose syntheses of alkenes and alkynes using elimination reactions.
38. Predict carbocation rearrangements and the limitations imposed on elimination reactions as a synthetic strategy.
39. Explain Zaitsev’s rule
40. Explain the acidity of terminal alkynes.
41. Write detailed reaction mechanisms for addition reactions to alkenes.
42. Explain Markovnikov’s rule.
43. Propose syntheses using addition reactions.
44. Predict the products formed upon oxidation of alkenes and alkynes.
45. Explain the origin of the signal in nuclear magnetic spectroscopy.
46. Interpret a proton nmr spectrum in terms of equivalence of protons, shielding of protons, chemical shift, and signal splitting.
47. Identify compounds based on their proton nmr spectrum.
48. Explain the origin of the mass spectrum.
49. Explain the basis of usual fragmentations in the mass spectrum
50. Interpret a mass spectrum in terms of ion intensities and fragmentation patterns.
51. Identify compounds based on their mass spectrum.
52. Identify compounds based on their combined mass spectrum, NMR spectrum, and IR spectrum
53. Practice standard laboratory safety precautions.
54. Communicate the results of laboratory work.
55. Use common organic laboratory techniques, including melting point determination, recrystallization, extraction, distillation, and chromatography.
56. Given a simple outline, develop the procedural detail for accomplishing a laboratory objective.
57. Purify compounds, separate mixtures, and identify unknown components using standard organic laboratory techniques.
58. Use chemical reference material appropriately, developing efficiency in locating physical property, safety, and reaction condition information.
59. Work effectively in groups.