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.
*Some students will already possess the previous textbook for this course (Solomons & Fryhle, Organic Chemistry, Eighth Edition with Study Guide) and may continue to use the text.A course outline based on the Solomon’s text.
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 and Problems: 32-35, 39, 40; Chapter 17, Sections 17.2, 17.3; Chapter 20, Sections 20.3, 20.4.
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.
Chapter 7 Alkenes: Reactions and Synthesis Sections: 1-3, 7, 9, 10 Problems: 1-4, 13, 17, 23 (a-c), 24 (a-d), 26 (b, d), 40(a), 43(a, b), 48-50, 54. Also to be read: Chapter 17, section 17.7.
Chapter 8 Alkynes: An Introduction to Organic Synthesis Sections: 1, 2, 4, 6, 8-10 Problems: 1 (a, b, d-f), 2, 3, 8, 10, 11, 14 (a, b), 20, 30, 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, 30-32, 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. Problems: 1, 2, 7, 8, 10, 11, 14, 28, 29, 32 (a, c-f), 36, 38, 51. Also to be read: Chapter 17, Section 17.6.
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), 32 (b, c), 40.
Chapter 21 Carboxylic Acid Derivatives Sections: 1-9. Problems: 1-10, 13, 15, 16, 23c, 24, 30, 40, 44-46. Also identify the monomers in Chap 31 problem 14 (b,c,e).
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: 1-9, 14. Problems: 1-13, 24-29, 32, 33, 37-39, 53, 56.
Chem 233 Solomons & Fryhle Outline:
As with the McMurray text, there is a significant amount of material from Chem 123 that students are expected to review on their own. This material is found in Chapters 1-6 of the Solomons & Fryhle textbook.
Chapter 1 Chemical Bonding All Sections Problems: 1-6, 8, 10-17, 19-23, 25, 34. Optional Problems: 7, 18, 33, 34, 39.
Chapter 2 Functional Groups All Sections (omit Section 2.16) Problems: 1, 3, 5-7, 11-13, 15, 17, 18, 20-23, 25-28, 32-35, 37, 42. Optional Problems: 2, 4, 8, 9, 16, 36, 41.
Chapter 3 Acid and Bases All Sections Problems: 1-3, 10, 11, 14-22, 24, 27, 29, 31-33, 40. Optional Problems: 13, 28, 30, 36, 39 Also to be read: Chapter 17, Section 17.3.
Chapter 4 Alkanes Sections: 4.1, 4.1A-4.1C, to get the general idea, 4.2 - 4.4A, 4.4B, to get the general idea, 4.5-4.12, 4.12A, to get the general idea, 4.13-4.14, 4.15, to get the general idea, 4.16, 4.17A, 4.17C-4.18, 4.19, to get the general idea (examples will be covered later) Problems: 1, 2, 4, 5, 7-9, 11-13, 19, 22, 27, 29, 30, 32, 35, 37, 44, 45 (a, b, e). Optional Problems: 10, 15, 20, 31, 34, 39-41, 46, 51.
Chapter 5 Stereochemistry Sections: 5.1-5.10A, 5.10B-5.11 to get the general idea, 5.12-5.15, 5.16-5.18 to get the general idea Problems: 1, 2, 4, 7, 9, 11-14, 17-21, 24, 31, 33. Optional Problems: 5, 22, 23, 26, 35, 45.
Chapter 6 Nucleophiles, Carbocations, etc. The material on carbocation stability in section 6.11B is critical to understanding the material in Chapter 8. The entire chapter should be read to refresh your memory of the topics covered in Chem 123. All Sections (omit 6.15-6.) Problems: 1-4, 6, 9, 11, 13, 16, 24, 39 Optional Problems: 8, 14, 18, 20.
Chapter 7 Alkene and Alkyne Chemistry Sections; 7.1-7.4, 7.7, 7.10-7.15 (omit 7.14B) Problems: 1-3, 9, 14-17, 18, 20, 21, 25, 28, 32, 33, 37, 38. Optional Problems: 19, 24, 40-42, 46.
Chapter 8 Addition Reactions of Alkenes and Alkynes, Acidity of Terminal AlkynesSections: 8.1 - 8.2C, 8.3, 8.5, 8.12-8.14, 8.18-8.19. Problems: 1-3, 5-7, 13, 16, 24, 29 (not 29.b, c or e), 32, 36. Optional Problems: 8, 15, 17, 35, 37, 43, 48, 50, 52.
Chapter 13 Resonance Sections: 13.1-13.2, 13.2A to get the general idea, 13.3-3.8, but ignore the discussion of nonbonding and antibonding orbitals on p 583, 586, Problems: 2-6, 9, 10, 23, 34. Optional Problems: 18 (not 18f), 33, 38.
Chapter 14 Aromatic Compounds Sections: 14.1-4.9 (omit Figs 14.4 and 14.6 and the related discussion of molecular orbitals) Also omit 14.7B NMR spectroscopy of aromatics. Problems: 1, 2, 8, 9, 12 Optional Problems: 13, 17, 18, 20, 23
Chapter 16 Aldehydes and Ketones Sections: 16.1-16.3, 16.5B, 16.6-16.9, but omit 16.7D thioacetals, 16.13. Problems: 1, 2, 4 (a, d–h), 5-14, 16, 23, 24 (a-d, g, k, m, n), 25 (a, b, c, g, k, m, n), 28 (all except i, q), 35, 49 Optional Problems: 3, 37, 40, 47
Chapter 12 Grignard Reagents Sections: 12.6-12.8 Problems: 7, 9 Optional Problems: 8, 10 (not b) Oxidation/Reduction Sections: 12.1-12.3 to get the general idea, know the lithium and aluminum reagents (not copper), 12.4A (no mechanism), 12.4C (no mechanism)
Chapter 22 Carbohydrates Sections: 22.1-22.4, 22.6A-22.6C, 22.7-22.13 (omit 22.9B), 22.11 only to get the general idea Problems: 1-6, 11-13, 15, 20, 28. Optional Problems: 14, 17, 21, 27.
Chapters 18, 23 Carboxylic Acids and Their Derivatives Sections: 18.1 18.2I, 18.4- 18.8F, 18.8H-18.HI, 18.10, 23.1-23.2A, 23.2C. Problems: 1–3, 5 (a, b, d, I), 6 (b, e, f), 7 (a, b), 10, 11, 14, 16b, 19 (a–d), 20, 23 (a, b), 24e, 25 (a-c), 29 (a–d), 30 (a, b). Optional Problems: 4, 8, 9, 29f, 37, 39.
Chapter 17 Enolates and Aldol Type Reactions Sections: 17.1-17.5A, 17.6-17.7. Problems: 1-14,18-22, 28 (a-d, f-I), 29 (a-d, f-I), 30 (not e, f, h), 31 (not c, g). Optional Problems: 23, 28 (e, l), 29 (e, l), 42.
Chapter 19 Beta-Dicarbonyl Compounds Sections: 19.1-19.3A, 19.3C-19.4, 19.6. Problems: 1-8, 10-14, 25 (not g, h). Optional Problems: 15, 16, 26 (not a), 27-29, 32, 41, 45, 47, 48.