Instructor Information: Dr. Daniel J. T. Myles Office: Gilbert Hall 145 Phone: 541-737-6756 E-mail: daniel.myles@oregonstate.edu All course information, updates, and announcements are posted via Blackboard at: http://my.oregonstate.edu/ Office Hours: MW, 1530 1700 Meeting Information: Lecture Days: Monday, Wednesday, and Friday Lecture Times and Location: Section 020 1400 1450 in MLM 026 Section 040 1100 1150 in GLFN AUD First and Last Days of Term: Monday, September 24 and Friday, November 30 Exam 1: Thursday, October 25 (2030 2150) Exam 2: Thursday, November 15 (2030 2150) Final Exam: Wednesday, December 05 (0730 0920) Tentative Course Outline: Chapter 1 Chapter 2 Chapter 3 Chapter 4 Chapter 5 Chapter 6 Chapter 8 Chapter 9 Electronic Structure and Bonding An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure Alkenes: Structure, Nomenclature, and an Introduction to Reactivity The Reactions of Alkenes Stereochemistry: The Arrangement of Atoms in Space The Reactions of Alkynes: An Introduction to Multistep Synthesis Substitution Reactions of Alkyl Halides Elimination Reactions of Alkyl Halides Resources and Materials: Page 1 of 6
Bruice, P. Y. Organic Chemistry, 6 th 2011. Edition, Pearson/Prentice Hall, Required Organic Molecular Modeling Kit (any number of acceptable kits will suffice) Bruice, P. Y. Organic Chemistry, Study Guide and Solutions Manual, 6 th Edition, Pearson/Prentice Hall, 2011. Required Optional Midterm Examinations: Two midterm exams (Exam 1 on Thursday, October 25; and Exam 2 on Thursday, November 15) will be administered outside of class. These exams will contain problems similar to those discussed in lecture and the ones assigned from the course textbook. These exams are 80 minutes long. Because exams are promptly marked and returned to the students, no make-up exams can be administered. A missed exam will receive a score of zero. Final Examination: The final exam will be administered on Wednesday December 05 (0730 0920). Please be on time. A late student may disturb the other students. The final exam is comprehensive. A missed final exam will receive a score of zero. Exam Supplies: 1. Several number two pencils and a good eraser. 2. Molecular model kit; however, the kit must be unassembled prior to the start of the exam. You must bring your OSU identification card to the exam and present it to the proctor upon completion of the exam. If you bring notes, papers, or books to the exam, place them in a sealed pack and place the pack at the front of the classroom. All audio devices, including CD/MP3 players and mobile telephones, must be turned off and put away during the exam. Evaluation: Maximum Points Page 2 of 6
Midterm Examination 1 100 Midterm Examination 2 100 Final Examination 150 (or 350)* Blackboard Quizzes 60 Final Score 410 *If the percentage a student earns on the final exam is higher than the average of the two-midterm scores, the points earned on the final exam will be used to determine the overall exam score. Course grades are based on your overall score according to the following: Letter Grade Minimum Score Needed out of 410 Corresponding Percentage A 377 92% A 369 90% B+ 361 88% B 336 82% B 328 80% C+ 320 78% C 295 72% C 287 70% D+ 279 68% D 254 62% D 246 60% F less than 246 <60% This course is primarily based on lecture material. The textbook is provided as a learning resource and for practice problems. Students are expected to attend lectures and are responsible for all lecture material missed for any reason. The instructor will not give make-up lectures during office hours. Homework: Page 3 of 6
Homework problems from the textbook can be found in the Lecture Schedule and Homework document under Course Information. These problems will not be graded or collected; however, they are absolutely essential to your success in the course! Blackboard Quizzes: Six quizzes will be given throughout the term. These quizzes are open book and open note. You are encouraged to work with your fellow students to answer the questions. The quiz schedule is shown directly below: Quiz Post Mon. at 10 AM Due Fri. at 5 PM 1 Oct. 1 Oct. 5 2 Oct. 8 Oct. 12 3 Oct. 15 Oct. 19 4 Oct. 29 Nov. 2 5 Nov. 5 Nov. 9 6 Nov. 26 Nov. 30 Recitations: Recitations are 50-minute meetings that are led by a graduate teaching assistant (TA). Students are scheduled for one recitation per week and must attend the recitation section for which they are scheduled! Recitation sections are intended to provide the students with an opportunity to ask questions about the material and for the TAs to reinforce material covered during regular lectures. Student Resources: Your success in CH 331 is very important to me! You have the following resources to help you with your study: 1. Lecture and Recitation Meetings 2. Academic Success Center (http://success.oregonstate.edu/) 3. Textbook Readings 4. Instructor Office Hours (MW, 1530 1700) Accommodations for Students with Disabilities: Accommodations are a collaborative effort between students, faculty, and Disability Access Services (DAS). Students with accommodations approved through DAS are responsible for contacting the faculty member in charge of the course prior to or during the first week of the term to discuss accommodations. Students who believe they are eligible for accommodations but have not yet obtained approval through DAS should contact DAS immediately at 737-4098. Page 4 of 6
Academic Dishonesty: You will be expected to conduct yourself in a professional manner. Academic dishonesty such as plagiarism and cheating will not be tolerated. Therefore, students are expected to be honest and ethical in their academic work. Academic dishonesty is defined as an intentional act of deception in one of the following areas: * cheating- use or attempted use of unauthorized materials, information or study aids, * fabrication- falsification or invention of any information, * assisting- helping another commit an act of academic dishonesty, * tampering- altering or interfering with evaluation instruments and documents, or * plagiarism- representing the words or ideas of another person as one's own. For more information about academic integrity and the University's policies and procedures in this area, please refer to the Student Conduct website at: http://oregonstate.edu/admin/stucon/achon.htm Student Learning Outcomes The successful student will: 1. Nomenclature a. be able to give IUPAC names of alkanes, cycloalkanes, alkenes, alkyl halides and alkynes 2. Drawing conventions a. be able to use/interpret perspective formulas, Newman projections and Fischer projections 3. Lewis acid/base chemistry a. given the reactants be able to predict the products and display the mechanism via curved arrow formalism 4. Alkanes/cycloalkanes a. be able to estimate strain energies of simple alkanes, cycloalkanes and subsituted cyclohexanes b. be able to determine the preferred conformation of a substituted cyclohexane 5. Alkenes a. given the reactants be able to predict the products of alkene hydrohalogenation, hydration, halogenation, oxymercuration-reduction and hydroboration-oxidation, predict and explain the distribution of products and display the mechanism via curved arrow formalism b. given the reactants be able to predict the products of alkene hydrogenation, hydroxylation and oxidative cleavage and predict and explain the distribution of products 6. Alkyl halides Page 5 of 6
a. given an alkyl halide substrate in conjunction with a nucleophile or base be able to predict the product(s), including stereochemical outcome, of substitution (S N 1/S N 2) or elimination (E1/E2), predict and explain the distribution of products and display mechanism via curved arrow formalism b. you know the differences and similarities between a nucleophile and a base and their use in substitution and elimination c. be able to recognize likely substrates for S N 1/S N 2 substitutions and E1/E2 eliminations in terms of leaving group and alkyl halide substrate degree (i.e., methyl, primary, secondary, or tertiary) 7. Alkynes a. given the reactants be able to predict the products of alkyne hydrohalogenation, hydration, halogenation, and hydrogenation, predict and explain the distribution of products and display the mechanism via curved arrow formalism b. you understand how alkyne products are prepared from double elimination of dihalides and display the mechanism via curved arrow formalism c. you understand the formation of acetylide ions from deprotonating terminal alkynes and their subsequent use in substitution chemistry and display mechanistic details via curved arrow formalism 8. Stereochemistry a. you understand the core concept of "chirality" and can describe this in terms of "handedness" or of superimposability of a mirror image. In addition, you can recognize achiral objects that contain an internal plane of symmetry b. you can describe the relationship between the presence of one or more asymmetric center and the chirality of a molecule (or the lack thereof) c. you can use the Cahn-Prelog-Ingold system to identify group priorities around an atom and define whether the absolute stereochemistry of a particular compound is R or S d. you know the definitions of key stereochemical relationships: enantiomers and diastereomers e. you know the impact of chirality on "optical activity" (rotation of the plane of polarization for plane-polarized light). You understand the consequence on optical activity for mixtures of stereoisomers Page 6 of 6