| Spring 2002 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| MWF 10:00; Th 8:00 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| OH-120 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Text: Organic Chemistry, 5th Edition by John McMurry | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| The Study Guide/Solutions manual accompanying this text is very useful. However, you should refer to these solutions only after you have attempted each problem! | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Models: Models are not required for this course, however there is no substitute for building a molecular model and viewing it from all angles. I have several model kits that can be checked out for the semester. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Computer Opportunities: Excellent links to organic chemistry resources can be found through the Millsaps Chemistry Department web page. Also check your e-mail often as I will occasionally send you messages. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Objectives: The primary objective of this course is to provide students with anappreciation and understanding of the basic concepts involved in organicchemistry. Students will be introduced to alkyl halides, benzene compounds, alcohols, epoxides, amines, carbonyl compounds, carbohydrates, and amino acids. Emphasis will be placed on structure, stereochemistry, synthesis, chemical reactions, and physical properties of these compounds. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Requirements: Chemistry 2110 is a pre-requisite for this course and Chemistry 2121 is to be taken concurrently. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Attendance: Class exercises, quizzes, and group discussions will not always be announced, therefore regular class attendance is required for optimum understanding and performance in this course. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Note: Students with learning disabilities or other disabilities are encouraged to contact me after class to discuss individual needs for accommodations. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Grading: The course grade will be based on three exams (100 points each), weekly quizzes, class exercises, or homework (10 points each), and a final comprehensive standardized exam (150 points). The three lowest quiz scores will be dropped. If a student misses a quiz/class exercise, it will automatically become one of the grades dropped. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Grading in this course will be on a curve with
cut-off points no higher than those shown below.
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Tentative Exam Schedule:
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| Makeup Policy: Makeup
exams are only available to those students with a written excuse from a
physician or a school-related absence. If you know that you will
be unable to attend one of the exams, you are required to notify me prior
to the exam so appropriate arrangements can be made.
E-mail requests for makeups immediately prior to or after an exam will not be allowed. This policy will be strictly applied. |
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| Grading errors: For consideration of a possible grading error on an exam or quiz, you must return it to me within one week of the date I hand it back to you. Furthermore, you must include a clear written statement of why you feel you deserve more credit. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Homework: Memorization
is not the most effective technique for success in organic chemistry.
There simply is too much material! Students must learn to view the
material in a systematic, logical manner and identify connections and relationships.
In fact, one of the greatest benefits of mastering organic chemistry is
learning to think logically.
One of the most important methods for learning organic chemistry is through working problems, lots of problems. In other words, you must understand how to work the assigned problems and apply that understanding to other problems in order to do well in this course. A list of suggested problems from the book is provided in the Course Outline section. These problems will not be collected or graded, so it is very important to keep your motivation high and work these problems diligently. In fact, plan to spend at least 3 hours studying and working problems outside of class for every hour in class. I strongly urge you to form study groups and work collaboratively at problem solving! This philosophy will work best if group problem solving is used in conjunction with independent study of the material. Do not wait until just prior to an exam to work problems. Procrastination is a recipe for disaster in organic chemistry. |
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| Organic chemistry is not hard…it just requires
hard work!
To be successful: 1) Attend lectures and take clear notes. 2) Review your notes before class and ask questions at the beginning of class. 3) Read the appropriate section of the text before lecture! 4) Complete the assigned problems. 5) Keep an open mind. 6) Remember that I am always here to assist you in your studies!!! |
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| Honor Code: This
course operates under the guidelines defined by the College Honor
Code (refer to Major Facts pages 38-41). Unless otherwise noted, all work turned in for a grade is pledged to be your own. |
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| Changes: Changes to this syllabus are not anticipated, but if necessary they will be announced in class. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Course Outline: (Tentative Timeline) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alkyl Halides: Chapter 10
(January 14-17)
Section 10.1 Nomenclature Section 10.3 Synthesis Section 10.4 Radical Halogenation of Alkanes Section 10.5 and 10.6 Allylic Bromination of Alkenes Section 10.7 From Alcohols Section 10.8 Reactions of Alkyl Halides and Grignard Reagents Section 10.9 Organometallic Coupling Problems: 10.1, 10.2, 10.3, 10.4, 10.6, 10.7, 10.8, 10.9, 10.10, 10.11, 10.12, 10.14, 10.17, 10.18, 10.21, 10.23, 10.24, 10.32 |
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| Reactions of Alkyl Halides:
Chapter 11 (January 18-25)
Section 11.2 Stereochemistry of Nucleophilic Substitution Section 11.3 Kinetics of Nucleophilic Substitution Section 11.4 SN2 Section 11.5 Characteristics Section 11.6 SN1 Section 11.7, 11.8, 11.9 Characteristics Section 11.10 Elimination Reactions of Alkyl Halides and Zaitsev’s Rule Sections 11.11 and 11.12 E2 periplanar vs. antiperiplanar Section 11.14 E1 Section 11.15 Summary of Reactivity Section 11.16 Substitution Reactions in Synthesis Problems: 11.1, 11.2, 11.3, 11.4, 11.5, 11.6, 11.7, 11.8, 11.9, 11.12, 11.13, 11.14, 11.15, 11.16, 11.17, 11.19, 11.20, 11.26, 11.27, 11.28, 11.29, 11.31, 11.32, 11.33, 11.34, 11.35, 11.36, 11.37, 11.39, 11.40 |
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| Benzene and Aromaticity:
Chapter 15 (January 28-February 1)
Section 15.2 Nomenclature Section 15.3 Structure and Stability of Benzene -MO Description (Sections 15.4 and 15.8) Section 15.5 Huckel Rule (4n + 2) Section 15.6 Aromatic Ions Section 15.7 Aromatic Heterocycles Section 15.9 Polycyclic Aromatic Compounds Problems: 15.1, 15.2, 15.3, 15.4, 15.7, 15.8, 15.9, 15.10, 15.11, 15.12, 15.13, 15.17, 15.18, 15.22, 15.23, 15.30, 15.32, 15.33 |
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| Electrophilic Aromatic Substitution:
Chapter 16 (February 4-15)
Sections 16.1 and 16.2 Introduction Section 16.3 Friedel-Crafts Alkylation Section 16.4 Friedel-Crafts Acylation Section 16.5-16.7 Substituent Effects in Substituted Aromatic Rings -Inductive, Resonance, Ortho/para/meta directors Section 16.8 Nucleophilic Aromatic Substitution Section 16.10 Oxidation Section 16.11 Reduction Section 16.12 Synthesis of Substituted Benzenes Problems: 16.1, 16.2, 16.3, 16.4, 16.5, 16.6, 16.7, 16.8, 16.9, 16.10, 16.11, 16.12, 16.13, 16.14, 16.15, 16.16, 16.17, 16.18, 16.19, 16.21, 16.22, 16.23, 16.24, 16.27, 16.28, 16.29, 16.31, 16.32, 16.33, 16.34, 16.35, 16.38, 16.39, 16.40, 16.42, 16.44, 16.46, 16.47, 16.49, 16.70 |
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| Alcohols and Phenols: Chapter
17 (February 18-22)
Section 17.1 Nomenclature Sections 17.2-17.3 Properties -Hydrogen bonding, Acidity and Basicity Sections 17.4-17.6 Synthesis of Alcohols Section 17.7 Reactions of Alcohols -Dehydration -ROH ® RX -ROH ® Tosylate -Oxidations (17.8) Section 17.9 Protecting Groups for Alcohols Section 17.10 Synthesis and Use of Phenols Section 17.11 Reactions of Phenols Problems: 17.1, 17.2, 17.3, 17.4, 17.5, 17.6, 17.7, 17.8, 17.9, 17.10, 17.11, 17.12, 17.13, 17.14, 17.16, 17.24, 17.27, 17.29, 17.30, 17.32, 17.34, 17.41, 17.43, 17.54 |
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| Ethers and Epoxides; Thiols and
Sulfides: Chapter 18 (February 25-March 1)
Section 18.1 Nomenclature Section 18.2 Properties Section 18.3 Williamson Ether Synthesis Section 18.4 Alkoxymercuration of Alkenes Section 18.5 Reactions -Acidic Cleavage -Claisen rearrangement (18.6) Section 18.7 Cyclic Ethers: Epoxides Section 18.8 Ring-Opening Reactions of Epoxides Section 18.9 Crown Ethers Section 18.11 Thiols and Sulfides Problems: 18.1, 18.3, 18.4, 18.5, 18.6, 18.7, 18.8, 18.10, 18.11, 18.12, 18.13, 18.14, 18.15, 18.16, 18.18, 18.19, 18.21, 18.25, 18.26, 18.27, 18.28, 18.30 |
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| Aldehydes/Ketones: Nucleophilic
Addition: Chapter 19 (March 4-22)
Section 19.1 Nomenclature Section 19.2 Synthesis Section 19.3 Oxidation Reactions -Jones’ and Tollens’ reagent Section 19.4 Nucleophilic Addition Reactions -relative reactivity (19.5) -Hydration (19.6) -Cyanohydrins (19.7) -Alcohol formation (19.8) Section 19.9 Nucleophilic Addition of Amines Section 19.10 Wolff-Kishner Reaction Section 19.11 Acetal Formation Section 19.12 Wittig Reaction Section 19.13 Cannizzaro Reaction Section 19.14 Conjugate Addition Problems: 19.1, 19.2, 19.3, 19.4, 19.5, 19.6, 19.7, 19.10, 19.11, 19.13, 19.15, 19.17, 19.18, 19.25, 19.28, 19.29, 19.30, 19.31, 19.32, 19.37, 19.38, 19.39, 19.44 |
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| Carboxylic Acids: Chapter
20 (March 25-28)
Section 20.1 Nomenclature Section 20.2 Physical Properties Sections 20.3-20.4 Acidity Section 20.6 Synthesis Section 20.7 Reactions -Reduction (20.8) Problems: 20.1, 20.2, 20.5, 20.9, 20.10, 20.18, 20.20, 20.21, 20.22, 20.29,20.31, 20.34 |
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| Carboxylic Acid Derivatives and
Nucleophilic Acyl Substitution Reactions:
Chapter 21 (April 1-5) Section 21.1 Nomenclature -Acid Halides, Acid Anhydrides, Amides, Esters, Nitriles Section 21.2 Nucleophilic Acyl Substitution Sections 21.3-21.8 Reactions Problems: 21.1, 21.2, 21.3, 21.4, 21.5, 21.6, 21.8, 21.9, 21.11, 21.13, 21.14, 21.15, 21.18, 21.19, 21.20, 21.21, 21.22, 21.23, 21.24, 21.35, 21.38, 21.40, 21.47 |
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| Carbonyl a-Substitution Reactions:
Chapter 22 (April 8-11)
Section 22.1 Keto-Enol Tautomerism Section 22.2 Mechanism Section 22.3 Alpha Halogenation Section 22.5 Enolate Ion Formation Section 22.6 Reactivity of Enolate Ions Problems: 22.1, 22.2, 22.3, 22.4, 22.7, 22.20, 22.21, 22.22 |
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| Carbonyl Condensation Reactions:
Chapter 23 (April 12-17)
Section 23.1 Mechanism Section 23.2, 23.4, 23.6 Aldol and Mixed Aldol Reactions Section 23.7 Intramolecular Aldol Reactions Section 23.8 Claisen Condensation Reaction Section 23.11 Michael Reaction Problems: 23.1, 23.2, 23.3, 23.5, 23.7, 23.9, 23.10, 23.15 |
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| Amines: Chapter 24
(April 18-22)
Section 24.1 Nomenclature Section 24.2 Structure and Bonding Section 24.3 Physical Properties Sections 24.4 and 24.5 Basicity Section 24.6 Synthesis -Reductive Amination -Hofmann and Curtius Rearrangement Sections 24.7 and 24.8 Reactions Section 24.9 Phase Transfer Catalysts Problems: 24.1, 24.2, 24.3, 24.4, 24.5, 24.6, 24.7, 24.11, 24.12, 24.18 |
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| Carbohydrates: Chapter 25
and Amino Acids: Chapter 26 (April 24-25)
Section 25.1 Classification Section 25.2 Fischer Projections Section 25.3 D, L sugars Section 25.5 Hemiacetal Formation Section 26.1 Structure Section 26.5 Peptides and Proteins Section 26.6 Covalent bonding in Peptides |
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