Textbook: Organic Chemistry, Sixth Edition, by John McMurry
NOTE: The student should make good use of Appendix C (pp. A-9-A-30) of the textbook, which contains a very useful glossary of terms used in organic chemistry.
Chapter 1 Structure and Bonding. All Sections. This chapter contains basic information about structure and bonding (subject matter that Chemistry 203 students have encountered before) and each student is responsible for doing a thorough review of the material covered in this chapter. Doing the assigned problems will assist the student in learning from the review process. Problems: 3, 4, 6, 8, 10, 12-16, 27, 29-31, 38, 39, 45
Chapter 2 Polar Bonds and Their Consequences. All Sections. The ideas and concepts covered in this chapter are basic to an understanding of the structure and reactivity of organic compounds. Most of this material will be discussed in class. Problems: 2, 3, 5-15, 17, 18, 21, 22, 31, 35-37, 40-45, 53, 54, 56, 57.
Chapter 3 Organic Compounds: Alkanes and Cycloalkanes. All Sections. Essentially all of the material presented in this chapter was covered in Chemistry 123 (January-April, 2003) and will not be repeated in Chemistry 203. Each student is responsible for doing a thorough review of the material covered in this chapter. Doing the assigned problems will assist the student in learning from the review process. Problems: 1-13, 15, 16, 18, 19, 23, 26, 33, 34, 39, 45, 49, 51, 53, 54.
Chapter 4 Stereochemistry of Alkanes and Cycloalkanes. Sections 1-13. Essentially all of the material presented in this chapter (sections 1-12, inclusive) was covered in Chemistry 123 (January-April, 2003) and will not be repeated in Chemistry 203. Each student is responsible for doing a thorough review of the material covered in sections 1-13 of this chapter. Doing the assigned problems will assist the student in learning from the review process. Problems: 1, 2, 3 (a,b), 4, 8, 9, 11-14, 15, 17 (a,c,d), 24, 25, 34-38, 40, 49, 54.
Chapter 5 An Overview of Organic Reactions. All Sections. Much of the material presented in this short chapter will be covered in the remainder of Chemistry 203. The student should consult this chapter regularly and use it to review the course material.
Chapter 6 Alkenes: Structure and Reactivity. Sections: 1-10. Problems: 1-7, 10-13, 14 (a,b,d), 15 (a-c), 23 (a-c), 24, 26, 29-31, 34, 39 (a-c), 40, 42, 43, 53.
Chapter 7 Alkenes: Reactions and Synthesis. Sections: 1-3, 5, 7, 8. Problems: 1-6, 9-11, 13, 14 (a,b),16, 23, 24 (a-d), 25(a,c), 26 (a,b,d-f), 27-29, 31, 34, 38, 40, 41, 48, 49, 52.
Chapter 8 Alkynes: An Introduction to Organic Synthesis. Sections: 1-3, 6, 8-10. Problems: 1 (a,b,d-f), 2, 8, 10, 11, 14 (a,b), 20, 27 (b,c), 30, 37 (a-c), 38, 40, 41.
Chapter 9 Stereochemistry. All Sections except 9.17. Much of the material in this chapter was covered in Chemistry 123 (January-April, 2003). The Chemistry 123 course included discussions of the following (a) stereoisomers (b) enantiomers (c) chirality (d) chirality centers (e) stereogenic centers (f) optical activity (g) specific rotation (h) R and S convention for designation of configuration of chirality centers (i) diastereomers (j) meso compounds (k) racemic compounds and their resolution into two enantiomers (l) Fischer projections. Although these concepts will be reviewed briefly in Chemistry 203 and will be used in the remainder of the course (and in Chemistry 204), they will not be discussed in detail. Each student is responsible for doing a thorough review of the material covered in Chapter 9 of the text. Doing the assigned problems will assist the student in learning from the review process.Problems: 1-16, 18-23, 27-30, 33-36, 38-42, 44-48, 50-55, 68, 80-83.
Chapter 10 Alkyl Halides. Sections: 1-7. Problems: 1-3, 5, 6, 8, 17-20, 23 (a-d), 24, 25, 32, 39.
Chapter 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations. All Sections. A good portion of this chapter was covered in Chemistry 123 (January-April, 2003). The Chemistry 123 course included discussions of the following: (a) nucleophile (b) electrophile (c) SN2 mechanism (d) transition state (e) leaving groups (f) stereochemistry of the SN2 process (g) SN1 mechanism (h) carbocations - formation and relative stability (i) diastereomers. Although these topics will be reviewed briefly in Chemistry 203 and will be used in the remainder of the course (and in Chemistry 204), they will not be discussed in detail. Each student is responsible for doing a thorough review of this material as covered in Chapter 11 of the text. Doing the (appropriate) assigned problems will assist the student in learning from the review process. Problems: 1-12, 14, 17-20, 26, 27, 30-32, 35-40, 43, 44, 47-49, 54, 55-61
Chapter 12 Structure Determination: Infrared Spectroscopy. Sections: 5-9. Problems: 10, 11, 13, 14, 35-39, 42 (a,b,d), 43, 50.
Chapter 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy. Sections: 1-3, 8-11, 13. Problems: 3, 14-21, 24, 26 (1H NMR only), 31, 37, 39-43, 46, 49, 50, 53, 57.
Pages 578-586 Brief Review of Organic Reactions. The student should use this summary as a (partial) review for the final examination. OMIT the following: Table 1, part 1: reactions d, h, i, j; Table 1, part 2: reactions a, b; Table 2, reaction 3; Table 3, reactions 3 and 4; Table 4: all; Pages 582-586: A.4, A.5, and C.
Chapter 17 Alcohols (Phenols are omitted). Sections: 1-8 (omit phenols), 12 (alcohols only, omit mass spectrometry). Problems: 1 (a-d), 2 (a-d), 4 (a), 7-12, 15, 19, 20, 21 (a-c), 24, 33-37, 50, 52 (a,b,d, ignore benzene as a possible starting material), 57, 58, 62-64.
Chapter 18 Ethers and Epoxides. Sections: 1-3, 5, 7, 8, 10. Problems: 1, 3, 4, 7-9, 11-15, 22, 24 (omit d), 26 (a,d), 27 (c,e,f), 30 (b,c,d) 31, 33, 37,38, 52, 56 (c)
Chapter 19 Aldehydes and Ketones: Nucleophilic Addition Reactions. Sections: 1-6, 8-12, 16 (IR and 1H NMR only). Problems: 1-3, 4 (c,d), 7, 8, 10, 11, 13-16, 28, 29, 32 (a,c-g), 34, 36, 37 (b), 38, 40 (a, c), 45, 49, 51, 63, 67, 68.