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.

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  
L16 Pericyclic Reactions - Cycloadditions  
L17 Pericyclic Reactions - Cycloadditions, Sigmatropic Rearrangements  
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.)  
L23 Carboxylic Acids and Derivatives (cont.)  
L24 Carboxylic Acids and Derivatives (cont.)  
L25 Enols and Enolates  
  Exam 3  
L26 Enols and Enolates (cont.)  
L27 Enols and Enolates (cont.)  
L28 Enols and Enolates (cont.)  
L29 Carbocations  
L30 Carbocations (cont.)  
L31 Carbocations (cont.)  
L32 Carbocations (cont.)  
  Exam 4  
L33 Radicals  
L34 Radicals (cont.)  
L35 Photochemistry