The assigned textbook for Chemistry 203 and 204 for the upcoming year will be:
Organic Chemistry (4th Ed.) by Brown, Foote and Iverson.
NOTE: The student should make good use of the glossary of terms found at the end of the textbook
(G.1-G.15), which contains definitions used in organic chemistry.
• Fundamental Concepts
Chapter 1 Covalent Bonding and Shapes of Molecules. All sections. This chapter contains basic
information about structure, bonding, resonance, and functional groups (subject matter that Chemistry
203 students have encountered before). 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, 5-12, 14-18, 23, 25-58, 66-70.
Chapter 2 Alkanes and Cycloalkanes. All sections except 2.4B and 2.7B. Essentially all of the
material presented in this chapter was covered in Chemistry 123 (January-April, 2006) 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: 1-4, 7, 8a,b, 9, 10, 12-15, 16-30, 32, 33, 34a,b,c, 35, 40-42, 46-49, 51, 52,
56, 58, 60, 61.
Chapter 3 Stereoisomerism and Chirality. All sections except 3.8B,C. Much of the material in this
chapter was covered in Chemistry 123 (January-April, 2006). 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 3 of the text. Doing the assigned problems will assist the student in learning from
the review process. Problems: 1-8, 10a, 13-18, 20-28, 30-32.
Chapter 4 Acids and Bases. All sections. Problems: 1-12, 15, 16, 19, 25, 29-32, 34, 36.
• Compounds with C-C p Bonds (Non-Aromatic)
Chapter 5 Alkenes: Bonding, Nomenclature and Properties. All sections except 5.4. Problems: 1-11,
13, 20, 24.
Chapter 6 Reactions of Alkenes. All sections except 6.3C, 6.3F, 6.7C. “Writing a Balanced Half-
Reaction” also will not be examined. Problems: 1-5, 7-9, 11, 12, 14, 15, 16 (not parts g or h), 17, 18
(not part e), 21, 22, 26 (very hard, for keeners only), 29, 32, 33, 36-38, 43, 44, 45 (not part a), 48-
50.
Summary of Stereochemical Terms (pp. 260-263). Students should make use of this useful
reference as appropriate.
Chapter 7 Alkynes. All sections except 7.6, 7.7, 7.8B. Problems: 1-3, 6, 8, 10, 11a-c.
• Compounds Containing Halogen Atoms
Chapter 8 Haloalkanes, Halogenation and Radical Reactions. All sections except 8.7 and 8.8.
Problems: 1, 2, 4 (don’t do the DHo calculation), 5, 8, 9, 10, 13, 24, 28a-e.
Chapter 9 Nucleophilic Substitution and b-Elimination. All sections except 9.4H, 9.10 and 9.11. A
good portion of this chapter was covered in Chemistry 123 (January-April, 2006). 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 9 of the text. Doing the (appropriate) assigned problems will assist
the student in learning from the review process. Problems: 1-8, 10-18, 21-26, 28-30, 34, 37-40, 42-
53.
• Spectroscopy
Chapter 12 Infrared Spectroscopy. All sections (Note: Section 12.4 contains more detail than
required for course, review it, but do not memorize frequencies). Problems: 3, 4, 6, 7, 10, 11.
Chapter 13 Nuclear Magnetic Resonance Spectroscopy. All sections except 13.9 contains more
detail than required for course, 13.10, 13.11, 13.12. **”How to Solve NMR Spectral Problems” (pp
530-532) is very useful.** Problems: 2-6, 10, 16, 18, 26.
• Compounds Containing C-O s and p Bonds
Chapter 10 Alcohols. All sections except 10.7 and 10.9 (also exclude discussions of rearrangements
of carbocations on pages 397 and 404-5). Problems: 1a,b, 2-8, 11, 14, 15a-j, 16c-g, k-n, 17-23, 25ae,
26-32, 35, 37, 38, 40-43, 45, 46, 48, 49.
The topic of “Alcohols” will include material dealing with the construction of alcohols:
Chapter 15 Organometallic Reagents. Section 15.1 Problems: 1, 2, 11.
Chapter 16 Aldehydes and Ketones. Section 16.5A, 16.5B, 16.11A. Problems: 18, 19
Chapter 11 Ethers, Sulfides and Epoxides. All sections except 11.6, 11.8D, 11.11, 11.12. Problems:
1-6, 8, 11, 13, 15, 17, 20, 21, 27, 33, 34, 35.
Chapter 16 Aldehydes and Ketones All sections except part of 16.5D, 16.6 (phosphonate esters),
16.8 (enamines), 16.10 (to be covered in C204), 16.12B, 16.12C Problems: 1-9, 12, 13, 15, 16, 18,
19, 21-23, 29-33, 38, 52, 59, 63, 64.