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Key
EA = Elemental Analysis
MS = Mass Spectrometry
IR = Infrared Spectroscopy
NMR = Nuclear Magnetic Resonance
Required Text
McMurry, John. Fundamentals of Organic Chemistry. 6th ed. Pacific Grove, CA: Thomson-Brooks/Cole, 2006. ISBN: 9780495012030.
Additional Texts
McMurry, Susan. Study Guide and Student Solutions Manual for John McMurry's Organic Chemistry. 6th ed. Belmont, CA: Thomson-Brooks/Cole, 2003. ISBN: 9780534409340.
Wade, L. G., Jr. Organic Chemistry. 5th ed. Upper Saddle River, NJ: Prentice Hall, 2002. ISBN: 9780130338327.
Clayden, J., et al. Organic Chemistry. Oxford, England: Oxford University Press, 2000. ISBN: 9780198503460.
Course readings.
| SES # |
TOPICS |
READINGS |
| L1 |
Molecular Formula and Index of Hydrogen Deficiency [EA] |
McMurry. Chapter 12, pp. 393-423, and Chapter 13, pp. 424-463.
|
| L2 |
Molecular Formula and Index of Hydrogen Deficiency [MS] |
|
| L3 |
Functional Groups [IR] |
|
| L4 |
Functional Groups: Fragmentation [MS] |
|
| L5 |
Functional Groups [13C NMR] |
|
| L6 |
Connectivity [1H NMR] |
|
| L7 |
Connectivity [1H NMR] (cont.) |
|
| L8 |
Organic Structure Elucidation |
|
| L9 |
Organic Structure Elucidation (cont.) |
|
|
Exam 1 |
|
| L10 |
Ethers, Epoxides, and Sulfides |
McMurry. Chapter 18, pp. 639-671.
|
| L11 |
Ethers, Epoxides, and Sulfides (cont.) |
|
| L12 |
Conjugated Systems and Molecular Orbital Theory |
|
| L13 |
Conjugated Systems and Molecular Orbital Theory (cont.) |
|
| L14 |
Pericyclic Reactions - Introduction |
McMurry. Chapter 14, pp. 464-497.
(Also review McMurry. Chapter 15, pp. 498-527.)
|
| L15 |
Pericyclic Reactions - Electrocyclic Processes |
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| L16 |
Pericyclic Reactions - Cycloadditions |
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| L17 |
Pericyclic Reactions - Cycloadditions, Sigmatropic Rearrangements |
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| L18 |
Pericyclic Reactions - Sigmatropic Rearrangements |
|
|
Exam 2 |
|
| L19 |
Amines |
Suggested Reading
McMurry. Chapter 24.
|
| L20 |
Amines (cont.) |
|
| L21 |
Carboxylic Acids and Derivatives |
Suggested Reading
McMurry. Sections 19.2-19.8, 19.11, 20.1-20.9, and 21.1-21.7.
|
| L22 |
Carboxylic Acids and Derivatives (cont.) |
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| L23 |
Carboxylic Acids and Derivatives (cont.) |
|
| L24 |
Carboxylic Acids and Derivatives (cont.) |
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| L25 |
Enols and Enolates |
|
|
Exam 3 |
|
| L26 |
Enols and Enolates (cont.) |
|
| L27 |
Enols and Enolates (cont.) |
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| L28 |
Enols and Enolates (cont.) |
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| L29 |
Carbocations |
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| L30 |
Carbocations (cont.) |
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| L31 |
Carbocations (cont.) |
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| L32 |
Carbocations (cont.) |
|
|
Exam 4 |
|
| L33 |
Radicals |
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| L34 |
Radicals (cont.) |
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| L35 |
Photochemistry |
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