General Overview:
The course builds on and operates under the assumption that students are familiar with the organic content presented in both CHEM 123 (113) and CHEM 203.
Evaluation: Midterms (two) 20%, Final 45%, On-line Quizzes 10%, Laboratory 25%
Content Summary:
1) General concepts: acid/base equilibrium and rationales, organic redox concepts, resonance and its effects on various systems
2) Carbohydrates: illustration of the chemistry of carbonyl reactions covered above. Basic descriptive terms (a, b anomers, D, L configurations, etc.) Fundamental chemistry. Disaccharides.
3) Nucleophilic Acyl Substitution: Preparation of carboxylic acids. Discussion of the interconversion of various acyl derivatives. Hydrolysis, alcoholysis, ammonolysis, reduction, Grignard reagent addition. Mechanistic emphasis.
4) a-Enolate Reactions: condensation reactions (aldol, Claisen – both simple, mixed, and intramolecular variations). Acetoacetic and Malonic ester synthesis. Mechanistic emphasis. Parallels to biochemical processes.
5) Aromaticity: basic introduction as an extension of resonance effects. Hückel Rule and recognition of aromatic systems; effects of aromaticity on acidity/basicity; benzylic reactivity.
6) Reactions of Benzene and Derivatives: Discussion of electrophilic aromatic substitution. Mechanistic emphasis.
7) Reactions of Amines: nucleophilic and basic properties
8) Carbon-Carbon Bond Formation and Synthesis: Introduction to some modern methods of carbon-carbon bond formation including alkene metathesis (Grubbs) and an example of another catalytically-based process (Heck).
Chem 204 Course Outline
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&IOrganic Chemistry, Fourth Edition
Prentice Hall Special Model Set (or equivalent)
*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 213 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 25Carbohydrates 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 17Carboxylic 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.