Instructor: Dr. Holly D. Bendorf
Office: 209 HBC
Phone: 4365, 327-2888
Office Hours: T 2:00 - 3:00 pm, W 10:00 - 11:20 am, F 10:00 - 11:20 am, and by appointment or walk-in.
Evening Help-Session: To be announced.
Course Description: CHEM 220, Organic Chemistry I, is an introduction to the study of the chemistry of carbon compounds. The course covers the chemistry of alkenes and alkynes, the substitution and elimination chemistry of alkyl halides, the theory and applications of infrared spectroscopy, and the strategies of organic synthesis. The laboratory portion of the course will introduce the student to a variety of techniques for the synthesis, purification, and analysis of organic compounds.
Text and Materials:
Materials in Chemistry Reading Room: Copies of several organic chemistry texts are available in the reading room. If you are not satisfied with Schmid's treatment of a topic in his text, feel free to consult one of the other textbooks--you may just find one you like. Also, these texts are excellent sources of extra practice problems. All of the texts have the generic title "Organic Chemistry" and are written by: Solomons, McMurray, Fessenden and Fessenden, and Morrison and Boyd.
Quizzes 105 points 12% Brief exam 65 points 8% Exams 300 points 35% Laboratory 230 points 27% Final 150 points 18% ------------------ 850 points 100%Final letter grades will be assigned as follows: 765-850 A, 680-764 B, 595-679 C, 510-594 D.
Exams: There will be three in-class exams on the following dates:
Wednesday, October 2; Wednesday, October 23; Wednesday, November 20.
The final exam will be administered on the day and time announced in the final exam schedule. A brief exam (or you can think of it as a large quiz) will be given on Friday, September 13.
Quizzes: Quizzes are an incentive to stay current with the course. They provide you with a means of evaluating your progress and allow you to identify any potential "trouble spots" before you get into an exam. Most quizzes will be announced, however "pop" quizzes on the previous lecture's material may also be given. Again, this is meant to encourage you to keep-up with the course and to see me or the tutor if you have any questions. The lowest quiz grade will be dropped.
Assignments From the Text: Practice problems will be assigned from the text at each class period. Although these problems will not be collected, it is strongly suggested that you complete these assignments and have any questions answered before the next class period. Lectures, pop-quizzes, and in-class and take-home assignments are prepared with the assumption that you have read and understand the assigned material and have completed the assigned problems.
Help-Session: The evening help session is an informal workshop where you will have the opportunity to ask questions, review lecture material, and work problems either individually or in groups.
Extra Credit: Extra credit points (3) can be earned by attending departmental colloquia. Extra
credit points can also be earned by writing a brief research paper on a mutually agreed upon topic (up to 15
points). Other types of extra credit projects may become available during the semester.
Extra credit is limited to 30 points.
Attendance: Regular attendance at lecture is expected, and repeated, unexcused absences will be penalized (3 points per absence). Attendance at quizzes, exams and laboratory meetings (including pre-lab) is mandatory. Make-ups are not permitted unless the absence has prior approval by me (usually, a case of medical or family emergency which can be documented). A single, cumulative make-up exam will be administered at the end of the semester. Quizzes cannot be made-up. In case of an emergency, I can also be reached at my home: 327-2888.
Participation: Participation is highly encouraged in lecture. Do not hesitate to stop me if I am going too quickly or have not explained something to your satisfaction.
Study Suggestions: CHEM 220 is a very cumulative course. Each section builds upon the material covered in the previous chapters and to succeed in this course you need to be fluent with one chapter before moving on to the next. Just like learning a foreign language or playing a sport, you need to practice a bit each day. Review your class notes, read the text, discuss the material with your classmates, quiz yourself, and most importantly: work lots of problems. And remember, my job is to help you learn organic chemistry--if you have questions, if you are not sure how to approach a type of problem, or if a concept is still a little unclear, ask me about it!
Course Outline: The outline is tentative and subject to change.
Date Subject Text Problems Aug. 26 Intro. to Organic 1.1-3 1.18-20 Aug. 28 Electron config., Lewis Structures 1.4-7 1.1-5,21,22 Aug. 30 Atomic and molecular orbitals 1.8-11,13 1.7-10 Sept. 2 Hybridization 1.14-16 1.25,27-33 Sept. 4 Ionic and covalent bonds, electronegativity 2.12-15 1.14,15,39-45 Sept. 6 Alkanes: properties, nomenclature QUIZ 2.1,2.4-9,11 2.1,4-8,10,32 Sept. 9 Alkanes: isomers Functional groups 2.3,12-15 2.2,22,25,28-30,31,39 Sept. 11 Conformations of alkanes 3.9,10;4.1-5 3.42;4.1,4,16,19 Sept. 13 Mini-exam Sept. 16 Conformations of alkanes 4.6-11 4.6-8,20,22 Sept. 18 Conformations of cycloalkanes 4.12-14 4.9-14,23-27,30 Sept. 20 Stereochemistry - chirality in carbon QUIZ 6.1-7,12-15 6.1-3,5-8,30,31 Sept. 23 Assigning absolute configuration (R/S) 6.2,8-10 6.9-12,18,33 Sept. 25 Enantiomers, diastereomers, meso forms 6.10-11 6.20,21,39,44,45 Sept. 27 Alkyl halides QUIZ 2.14 2.15,16 Sept. 30 Intro. to organic reactions, acid/base chem 3.1-7 3.1-3,6-12,14,16 Oct. 2 EXAM 1 Oct. 4 Resonance and arrow notation 3.1.12,3.8 3.17,18,27-30,38-40 Oct. 7 Kinetics and mechanism 3.11-17 3.22-24 Oct. 9 Sn2 reaction: Intro., kinetics, mechanism 12.1-3 12.1,17,18 Oct. 11 Sn2: leaving group, nucleophile QUIZ 12.4 12.2-5,20 Oct. 14 The Sn1 reaction, Sn1 vs. Sn2 12.5-7 12.7,8,27 Oct. 16 Acid-cat. substitutions, cation rearr. QUIZ 12.8-9 12.9,19,24,29,30 Oct. 18 No Classes Oct. 21 Elimination: The E1; acid cat. elim. 12.10-11,16 12.10,12,13,28,32 Oct. 23 EXAM 2 Oct. 25 The E2: mechanism, substrate, stereochem. 12.12-13 12.11,17,25 Oct. 28 E2: stereochem., bulky bases 12.14-15 12.18,19,23,31 Oct. 30 E1/E2/Sn1/Sn2 wrap-up. QUIZ 12.17-18 12.14,22,26 Nov. 1 IR spectroscopy: theory and applications 5.1-4,7 5.2-5,18,19 Nov. 4 IR spectroscopy, Degree of unsaturation 5.5-6,11 5.6-8,13-15,21-24 Nov. 6 Alkenes: properties, preparation QUIZ 7.1-5,18 7.1-9,12,31 Nov. 8 Alkene reactions: addition of HX 7.7-13 7.14,16-20,22,33,34 Nov. 11 Alkene reactions: mechanism, carbocations 7.14-17 7.23-26,36-41 Nov. 13 Alkene reactions:electrophilic additionQUIZ 8.1-4,8,9 8.1-4,11-14,15,38 Nov. 15 Alkene reactions: electrophilic addition 8.5-6,11 8.5-8,20,23,28,28,32 Nov. 18 Alkynes: structure and properties 9.1-4,9 9.1-4,22,23 Nov. 20 EXAM 3 Nov. 22 Alkynes: electrophilic addition 9.6-8 9.5,9-12,24 Nov. 25 Alkynes: acid-base chemistry 9.10-11 9.14-16,26,28 Nov. 27 No Classes Nov. 29 No Classes Dec. 2 Synthesis 9.12 9.18,27 Dec. 4 Synthesis QUIZ 9.29,30 Dec. 6 ReviewLaboratory: It is imperative that you come to the lab fully prepared. Careful planning and preparation before you arrive at the lab will allow you to complete your experiments in an efficient and safe manner. It is your responsibility to read and understand the lab procedure before you arrive at prelab. Missing or arriving late to prelab will result in a reduced lab grade (up to 5 points per violation) and/or dismissal from the lab.
The laboratory grade is worth a total of 230 points and is comprised of lab write-ups (190 points total) and lab quizzes (40 points).
Lab Safety: Unsafe behavior in the lab will not be tolerated and violations will be penalized. Repeated violations during a class may result in a zero for that lab. Keep in mind that lab safety includes laboratory hygiene. In the event that common areas are left dirty, (rotovaps, balances, melting point apparati, reagent hood) points may be deducted from the entire lab section. If you have any questions regarding lab safety, please do not hesitate to ask.
Week Dates Lab Assigned Reading Report due Reading for week:* 1 Aug. 27, 29 Check-in Chp. 1 2 Sep. 3, 5 Melting Points Chp. 2, 4, 5 3 Sep. 10, 12 Distillation Chp. 6, 7 2 4 Sep. 17, 19 Recrystallization of Benzoic Chp. 8-10 3 Acid and Naphthalene 5 Sep. 24, 26 Solubility Testing and Chp. 3, 8-10 Unknown Recrystallization 6 Oct. 1, 3 Unknown Recrystallization Chp. 14, 8-10 4 7 Oct. 8, 10 Nucleophilic Competition Chp. 19, 21 Quiz 1 5, 6 8 Oct. 15, 17 Extraction Chp. 11-13 9 Oct. 22, 24 Extraction Chp. 11-13 7 10 Oct. 29, 31 Dilantin, Part 1 Chp. 16-18 8,9 11 Nov. 5, 7 Dilantin, Part 2 Chp. 16-18 10 12 Nov. 12, 14 Cyclohexene Chp. 15 Quiz 2 11 13 Nov. 19, 21 Steam distillation of limonene Chp. 23, 25 12 14 Nov. 26, 28 Thanksgiving--No Labs 15 Dec. 3, 5 Limonene Characterization, Chp. 24 14, 15 Check-out*Late reports will be penalized 3% per school day. Lab quizzes are during week 7 and week 12.