The recommended textbook for this course is:
Organic Chemistry, Sixth Edition, by John McMurry
Other suggested materials are:
Study Guide and Solutions Manual for McMurry’s Organic Chemistry, Sixth Edition, by Susan McMurry
Prentice Hall Special Model Set (or equivalent)
In addition to the textbook ALL students are required to have registered for the Online 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 233 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 McMurray textbook. Students who have obtained this text (or others) without the OWL resource MUST purchase the OWL registration package from either the UBC Bookstore or from Discount Textbooks.
Suggested problems are given in conjunction with each 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. An access code may also be purchased 0n-line directly from the publisher by linking to: http://owl1.thomsonlearning.com/epithomson.htmland selecting a purchase code (12 month) for the McMurray textbook.
Chem 233 McMurray Outline:
Chapter 1 Structure and Bonding All Sections. This chapter contains basic information about structure and bonding (subject matter that Chem 233 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. Much of this material will be discussed in class. Problems: 2, 3, 5-15, 17, 18, 21, 22, 31, 35-37, 39-45, 53, 54, 56, 57. Also to be read: Chapter 10, Section 10.10 (Oxidation/Reduction) and Problems: 32-35, 39, 40; Chapter 17(Acidity/Basicity), Sections 17.2, 17.3; Chapter 20 (Acidity), Sections 20.3, 20.4; Chapter 24 (Basicity), Sections 24.4, 24.5.
Chapter 3 Organic Compounds: Alkanes and Cycloalkanes All Sections. Essentially all of the material presented in this chapter was covered in Chem 123 and will not be repeated in Chem 233. 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 was covered in Chem 123 and will not be repeated in Chem 233. 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.
Chapter 5 An Overview of Organic Reactions All Sections (omit 5.3). Much of the material presented in this short chapter will be covered in the remainder of Chem 233. The student should consult this chapter regularly and use it to review the course material. Again many of the concepts in this chapter were introduced in Chem 123.
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. Also to be read: Chapter 9, Sections 9.12, 9.14 Problems: 22, 23.
Chapter 7 Alkenes: Reactions and Synthesis Sections: 1-3, 7, 9, Problems: 1-4, 13, 23 (a-c, e), 24 (a-d), 26 (b, d), 40(a), 43(a, b), 48-50, 54. Also to be read: Chapter 9, Sections 9.13 Problems: 21, 22, 65 (a,b); Chapter 17, section 17.7.
Chapter 8 Alkynes: An Introduction to Organic Synthesis Sections: 1, 2, 4, 5 (enol concept), 6, 8-10 Problems: 1 (a, b, d-f), 2, 3, 8, 10, 11, 14 (a, b), 20, 37 (a-c), 38, 40.
Chapter 9 Stereochemistry All Sections (omit 9.17). Essentially all of the material in this chapter was covered in Chem 123. Topics covered included (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 used in Chem 233, 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, 44-55, 80-83.
Chapter 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and EliminationsSections: 1-9. Most of this chapter was covered in Chem 123. Topics covered included (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 concepts will be used in Chem 233, 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 assigned problems will assist the student in learning from the review process. Problems: 1-12, 14, 26, 27, 30, 31 (a-e), 32, 35-39, 41, 54, 55.
Chapter 15 Benzene and Aromaticity Sections: 1-7, 9 Problems: 1, 3, 9, 20, 21, 24, 26.
A Preview of Carbonyl Compounds (pages 672-681). All Sections.
Chapter 19 Aldehydes and Ketones: Nucleophilic Addition Reactions Sections: 1-6, 8, 9,11, 15. Problems: 1, 2, 7, 8, 10, 11, 14, 28, 29, 32 (a, c-f), 36, 38, 51. Also to be read: Chapter 17, Section 17.5, 17.6 (as they pertain to reactions with aldehydes and ketones).
Chapter 25 Biomolecules: Carbohydrates Sections: 1-7, 8 (omit the material on the Kiliani-Fischer synthesis and the Wohl degradation), 9-11 Problems: 1-19, 30, 32-41, 44. The Fischer Glucose structure proof is not to be memorized – an appreciation of the logic and the chemistry involved is expected.
Chapter 20 Carboxylic Acids Sections: 1-9 (omit material on nitriles) Problems: 1-3, 5, 6, 8, 20 (a-d), 33 (c, e), 40.
Chapter 21 Carboxylic Acid Derivatives Sections: 1-9. Problems: 1-10, 13, 15, 16, 23c, 24, 30, 40, 44-46.
Chapter 22 Carbonyl Alpha-Substitution Sections: 1, 2, 5, 6, 8. Problems: 1-4, 7, 11, 12, 14, 15, 21-23, 24 (a, b), 26, 27.
Chapter 23 Carbonyl Condensation Reactions Sections: 1-10, 14. Problems: 1-13, 24-29, 32, 33, 37-39, 53, 56.