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The primary aim of this course is to present organic chemistry as a vigorous science based on a well-developed theory and to show its application in society. To attain this end, the first semester of this two-semester course will:

• Include essential principles (such as nomenclature, molecular structure, functional groups, stereochemistry) and simple reactions (such as those of the aliphatic hydrocarbons, halides, alcohols, phenols and ethers) so as to give the student thorough training in the fundamentals of organic chemistry.
• Interpret organic reactions in terms of modern theories of electronic structure and geometry, thereby enabling the student to recognize the fundamental mechanisms which relate the many types of organic reactions.
• Involve the student in laboratory sessions which are designed to complement the lecture material so that a more thorough understanding of organic chemistry is achieved at the same time that practical laboratory techniques are developed. Some of these techniques include: gas chromatography, refractometry, polarimetry and infrared spectroscopy along with, fractional and vacuum distillations, and extractions.

After completing this course the student will be able to:

1. Describe a covalent bond in terms of molecular orbitals and the hybrid atomic orbitals which make them up.
2. Predict bonding types (ionic, coordinate covalent and polar covalent) from considerations of relative electronegativities of the atoms involved.
3. Recognize structural isomers, free radicals, carbanions and carbocations.
4. Write Lewis electron dot structures for organic compounds.
5. Draw condensed formulas and structures of organic compounds.
6. Recognize different functional groups: halides, alcohols, ethers, amines, aldehydes, ketones, carboxylic acids, amides, and esters.
7. Describe physical properties of molecules.
8. Explain infrared (IR) spectroscopy.
9. Determine the structure of a molecule from its IR spectrum.
10. Draw structures of alkanes and cycloalkanes.
11. Determine all constitutional isomers for alkanes through C7.
12. Name alkanes and cycloalkanes according to the IUPAC system given the structural formulas and vice versa. Do the same using common names.
13. Sketch conformations of alkanes and cycloalkanes using sawhorse, Newman and perspective representations.
14. Differentiate between homolysis and heterolysis of covalent bonds.
15. Define acids and bases according to both Bronsted-Lowry, and Lewis.
16. Use curved arrows to illustrate reactions.
17. Predict the strengths of acids and bases.
18. Predict the outcome of acid-base reactions.
19. Describe the relationship between structure and acidity.
20. Produce the mechanism of an organic reaction.
21. Contrast and predict physical properties of the alkanes and cycloalkanes.
22. Design and understand the mechanisms involved in the syntheses of alkanes and cycloalkanes using various methods.
23. Investigate and reproduce the steps involved in various combustion and substitution reactions of alkanes and cycloalkanes. Incorporate these steps into multistep syntheses.
24. Draw structures of alkenes.
25. Name alkenes according to the IUPAC system given the structural formula and vice versa. Do the same using common names.
26. Recognize and name cis-trans isomers of alkenes.
27. Contrast and predict physical properties of the alkenes.
28. Design and understand the mechanisms involved in the syntheses of alkenes using various methods.
29. Describe the mechanisms of reactions involving carbocation formation, and compare their relative stabilities predicting any rearrangements that might occur.
30. Define nucleophilic substitution reactions.
31. Describe the factors involved in reaction rates.
32. Compare SN1 and SN2 mechanisms.
33. Predict the results of a nucleophilic substitution reaction based on stereochemistry.
34. Define elimination reactions.
35. Compare E1 and E2 mechanisms.
36. Predict the product in a reaction that may undergo substitution and elimination.
37. Investigate and reproduce the steps involved in addition, substitution and polymerization reactions of alkenes. Incorporate these steps into a multistep synthesis.
38. Identify some simple compounds from a series of analytical results.
39. Draw structures of dienes and alkynes.
40. Name dienes and alkynes according to the IUPAC system given the structural formulas and vice versa. Do the same using common names.
41. Contrast and predict physical properties of dienes and alkynes.
42. Design and understand the mechanisms involved in the syntheses of dienes and alkynes using various methods.
43. Represent the contributing structures in molecules which result in resonance and the increase in stability known as the resonance energy.
44. Investigate and reproduce the steps involved in various addition reactions of alkynes. Incorporate these steps into multistep syntheses.
45. Explain the optical activities in a molecule in terms of the molecule's geometric orientation in space: stereochemistry.
46. Calculate the specific rotation of a molecule given experimental data.
47. Recognize and draw stereoisomers: enantiomers, diasteriomers, and meso forms.
48. Explain the resolution of enantiomeric pairs.
49. Sketch Fisher projections of molecules.
50. Specify a molecule's configuration using the Cahn-Ingold-Prelog convention.
51. Name alcohols and ethers according to the IUPAC system given the structural formulas and vice versa. Do the same using common names.
52. Contrast and predict physical properties of alcohols and ethers.
53. Describe the synthesis of alcohols from alkenes using different methods.
54. Describe the hydration of a double bond in both a Markovnikov and an anti-Markovnikov reaction.
55. Explain nuclear magnetic resonance (NMR) spectroscopy.
56. Determine the structure of a molecule from its ¹H and ¹³C NMR spectra.
57. Determine the structure of a molecule from its IR and NMR spectra.
58. Describe the reactions of alcohols in which the O-H bond is cleaved.
59. Describe the reactions of alcohols in which the C-OH bond is cleaved.
60. Convert an alcohol into an alkyl halide.
61. Show the mechanism of the synthesis of an ether from an alcohol.
62. Describe reactions of ethers.
63. Calculate heats of reaction from bond dissociation energies.
64. Conduct multistep syntheses.
65. Pack a fractionating column.
66. Construct apparatus for fractional distillation.
67. Use a heating mantle properly.
68. Inject samples of a distillate into a gas chromatograph and analyze the results using various methods.
69. Perform a vacuum distillation.
70. Operate a polarimeter.
71. Determine the presence of double bonds in a compound by oxidation with potassium permanganate.
72. Use a polarimeter to measure the optical rotation of a solution.
73. Prepare and use a calibration curve to determine the concentration of sugar in a syrup by refractometry.
74. Ascertain the distribution coefficient of propionic acid in a two-solvent mixture.
75. Perform a separation with a separatory funnel, and use a pipet.
76. Titrate a solution to determine its acidity, using a buret.
77. Sulfonate an aromatic compound, carefully controlling the temperature so that only the para product is obtained.
78. Operate a Fourier transform infrared (FT-IR) spectrometer and analyze various IR spectra.
79. Synthesize cyclohexene by the dehydration of cyclohexanol.
80. Operate a Fourier transform nuclear magnetic resonance (FT-NMR) spectrometer and analyze the ¹H and ¹³C NMR spectra of a synthesized product.
81. Calculate percent yield and theoretical yield.
82. Compare, experimentally, the results of competitive nucleophilic halogenation of a primary alcohol versus a tertiary alcohol.
83. Reflux a liquid.
84. Assemble a trap for acid gases.
85. Measure the relative amounts of chloro and bromobutanes in a sample by quantitative gas chromatography.
86. Using molecular models, construct enantiomers, diastereomers, meso forms, cis-trans isomers, and cyclic and non-cyclic conformers. Translate these into Fisher and Newman projections.