The recommended textbook* for this course is:
Organic Chemistry, Fourth Edition, by Brown, Foote and Iverson
Required Material:
OWL (On-line Web-based Learning) Access Card**
Other suggested materials are:
Study Guide and Solutions Manual for BF&I Organic Chemistry, Fourth Edition
Prentice Hall Special Model Set (or equivalent)
*Some students will already possess the previous textbook for this course (McMurray, Organic Chemistry, Sixth Edition with Study Guide) and may continue to use the text. A course outline based on the McMurray text is given following the BF&I outline.
**In addition to the textbook ALL students are required to have registered for the On-line Web-based Learning (OWL) resource. OWL will be used to assist students with the learning process and a portion of their final grade in CHEM 204 will be determined from the results of OWL assignments given throughout the term. A registration kit for OWL is included with all new purchases of the BF&I textbook. Students who have obtained this text (or others) without the OWL resource MUST purchase the OWL registration package from the UBC Bookstore.
Suggested problems are given in conjunction with each textbook chapter. It is recommended that all students do these problems. Some students may prefer to use the textbook problems as preparation for the OWL exercises; others may wish to do the suggested problems after having completed the OWL assignments.
CHEM 204 BF&I Outline:
Resonance/Acids and Bases The ideas and concepts covered in Chapters 1 and 4 and the associated additional readings in later chapters are basic to an understanding of the structure and reactivity of organic compounds. Virtually all of this material has been previously presented at some level and you should already be somewhat familiar with it. We will discuss acid/base concepts and resonance ideas in some detail.
Chapter 1 Covalent Bonding and Shapes of Molecules Sections 2, 6 Problems: 15, 16, 17, 50-54
Chapter 4 Acids and Bases Sections: All Problems: 1-3, 6, 7, 11, 12, 16, 23, 26, 31, 34, 38, 41, 42, 44, 46, 47. Also to be read: Chapter 16 (Aldehydes and Ketones) Section 16.9 A Chapter 16 Problems: 9; Chapter 17 (Carboxylic Acids) Section 17.4 Chapter 17 Problems: 2, 3, 25, 26, 28; Chapter 18 (Functional Derivatives of Carboxylic Acids) Section 18.2 Chapter 18 Problems: 2; Chapter 21 (Benzene and the Concept of Aromaticity) Section 21.4 A-C Chapter 21 Problems: 6, 32-38; Chapter 23 (Amines) Section 23.5 Chapter 23 Problems: 6-8. 30.
Chapter 25 Carbohydrates Sections: 1-5 (Omit 1D, 3D, 3E) Problems: 1-5, 7-13, 16-23, 24 (a, c, d, f), 25 (a, c, d, f), 26-28, 37, 38 (a-c).
Chapter 17 Carboxylic Acids Sections: All (Omit 5B, 7C) Also to be read Chapter 18 Section 18.4E Problems: 1, 4, 6-10, 14, 15, 18 (a, b, d), 19, 20, 22 (a-d), 32 (a-e, g), 34, 35, 38-40.
Chapter 18 Functional Derivatives of Carboxylic Acids Sections: All (Omit 1C on phosphate esters) Problems: 1, 3, 4, 6-8, 10, 11, 14-17, 19, 20, 23, 24, 26-28, 31, 32, 43.
Chapter 19 Enolate Anions and Enamines Sections: 1-4, 6, 7. Also to be read Chapter 16 Section 16.9 and Chapter 17 Section 17.9. Problems: 1-5, 6b, 10-12, 17, 18, 20, 21, 23, 25, 28, 32-34, 45.
Chapter 21 Benzene and the Concept of Aromaticity Sections: All (Omit 4E, 4F) Problems: 2, 5, 7-9, 11-16, 18, 21a, 25-29, 40, 49 (a-l) , 51, 61.
Chapter 22 Reactions of Benzene and Its Derivatives Sections: 1-2 Problems: 1-5, 7-9, 15-17, 19-21, 27, 38, 41, 49.
Chapter 23 Amines Sections: 1-8 (Omit 23.8 A-D) Also to be read: Chapter 16 Section 16.8 Problems: 1-5, 10, 12, 13, 16-19, 22, 25, 27, 33, 34, 43, 44-46, 54.
Chapter 24 Carbon-Carbon Bond Formation and Synthesis Sections: 1-3, 5 Problems: 1, 2, 4, 10-19, 23, 24.
CHEM 204 McMurray Outline:
Chapter 2 Polar Bonds; Acids and Bases All Sections The ideas and concepts covered in this chapter are basic to an understanding of the structure and reactivity of organic compounds. Virtually all of this material has been previously presented and you should be familiar with it. We will discuss acid/base and resonance concepts in some detail. Problems: 10-15, 17, 18, 36-49, 53, 54-57, 59. Also to be read: Chapter 17 (acidity/basicity), Section 17.3; Chapter 20 (acidity), Sections 20.3, 20.4, 20.5; Chapter 22 (enolates), Section 22.5; Chapter 24 (basicity), Sections 24.4, 24.5.
Chapter 25 Biomolecules: Carbohydrates Sections: 1-7 (omit the material on the Kiliani-Fischer synthesis and the Wohl degradation), 9-11 Problems: 1-21, 29, 30, 34, 39, 41-44, 46, 47, 57, 60. The Fischer Glucose structure proof is not to be memorized – an appreciation of the logic and the chemistry involved is expected.
A Preview of Carbonyl Compounds (pages 672-681). All Sections.
Chapter 20 Carboxylic Acids and Nitriles Sections: All Problems: 1-5, 8-13, 16 (b, c), 20-22, 25 (a-d), 26 (a-d), 38, 40 (b, c), 46b, 48, 49, 54, 56.
Chapter 21 Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution Reactions Sections: 1-7, 10 Problems: 1-10, 12, 13, 15-17, 19-22, 26-29, 35, 40, 42, 43, 45, 46, 51, 63-66.
Chapter 22 Carbonyl Alpha-Substitution Reactions Sections: 1, 2, 5, 6, 8 Problems: 1-4, 7, 8, 11, 13, 14, 16-18, 20, 22, 23, 24 (a, b), 26, 28, 29, 31, 32, 34, 35, 37-40.
Chapter 23 Carbonyl Condensation Reactions Sections: 1-10 Problems: 1-15, 23-25, 27-35, 37-41, 46 (a, c), 60.
Chapter 15 Benzene and Aromaticity Sections: 1-6, 8, 9, 10 (IR and 1H NMR only) Problems: 1-3, 6 (1H NMR only), 13, 18, 19, 21-27, 39, 44, 45.
Chapter 16 Chemistry of Benzene: Electrophilic Aromatic Substitution Sections: 1-7, 10-12 Also to be read: Chapter 17 Phenols Sections 1-3, 12 (material related to phenols). Chapter 16 Problems: 2, 3, 6-10, 12, 14, 15, 19, 23, 25, 29, 30, 32-34, 40, 42-44, 50c, 51 (b, d), 52 (a, b), 69a, 70. Chapter 17 Problems: 1e, 4 (b, c), 65.
Chapter 24 Amines Sections: 1-5, 6 (omit material on the Gabriel synthesis, and the Hofmann and Curtius rearrangements), 7 (omit Hofmann elimination), 8 (omit diazonium coupling reactions), 10 (IR and 1H NMR only) Problems:1, 2, 4-10, 17, 18, 20-22, 27, 30 (a-d, g, h), 31 (a, b, d), 32 (a, c, e, f), 36 (a-c), 38 (c, d), 41, 42, 44, 50, 51, 57, 59, 67.
Chapter xx Carbon-Carbon Bond Formation and Synthesis The McMurray textbook does not have a chapter directly comparable to that in BF&I. It is anticipated that a WebCT posting summarizing appropriate concepts will be available to all students. You may wish to read the material in the BF&I textbook.