Syllabus for CHEM 220 (and CHEM 220L) Introductory Organic Chemistry

Transcription

1 Syllabus for CHEM 220 (and CHEM 220L) Introductory Organic Chemistry Instructor: Dr. David Freistroffer Office: Lundberg 109C (in the fishbowl ) Phone: davidf@gwmail.gbcnv.edu Office hours: Mon and Wed 4:00PM-5:30 Tues and Thurs 10:00AM-11:00AM Or by appointment Course description: For CHEM 220 lecture: Principles of carbon chemistry. Covering covalent bonding, alkanes, alkenes, and alkynes, chirality, alcohols, ethers, benzene, amines, carboxylic acids, polymers, and carbohydrates. For CHEM 220L: Techniques employed in the preparation, separation, and identification of organic compounds. Prerequisite: CHEM 121, CHEM 122 recommended. Lecture is a corequisite for the lab. Comment on this prerequisite: the student should have a background in acid base reactions, pk a, equilibrium, chemical kinetics, and thermodynamics. These are subjects found in CHEM 122. Texts: Lecture Bruice, Essential Organic Chemistry, 2 nd edition (required); Lab Fessenden, Organic Laboratory Techniques, 3 rd edition (required). Method of instruction: Live lecture, laboratory, with online enhancements (WebCampus). Lab experiments: We will do several lab experiments this semester that are designed to teach you the essential methods used in organic chemistry. Many of these labs will take more than one week to complete. You will record your procedures, results, and some discussion of the results in you lab notebook. Once a lab is complete you will hand in a lab report on that lab. Since a lab may not be completed every week you may not need to hand in a lab report each week. The lab experiments are designed to be completed in the 2:45 lab periods that are scheduled for this course. If you are unable to complete them during the allotted time you will be required to come in during office hour or another agreed upon time to complete them. You must do this in order to write a complete lab report this is the mechanism by which an incomplete lab will affect your grade. I do not anticipate that this will be an issue if you come to lab prepared. Note on lab safety: The organic chemistry lab can be dangerous for students who are unprepared. You are responsible for understanding every apparatus that you use or asking for help. You are responsible for understanding the hazards of every chemical you use (see MSDS section below). Ask for assistance with anything that you are unsure of or uncomfortable with. Come to lab prepared! Most students that have taken organic chemistry remember the lab as one of the highlights of their undergraduate career. Lectures: There will be live lectures for this course. I will post powerpoints (or another file format) of the lecture on WebCampus before class. Print out these presentations and bring them with you to

2 class. The information on the powerpoints is highly abbreviated and we will be complemented by your note taking during lecture. Use of computers in this course: WebCampus: This course will make use of WebCampus. To log in, go to webcampus.gbcnv.edu. Your WebCampus ID is your Great Basin College address ID. If you don't have a GBC address or don't remember your address go to swami.scsr.nevada.edu or the Technology Help Desk helpdesk@gwmail.gbcnv.edu, or Passwords will be sent by mail to students who register for their course(s) 5 days before the semester begins. If you register after this time or did not receive a letter by mail, contact the Help Desk as soon as possible. I do not have the capacity to help you with computer-technical issues this semester. You will receive much faster and more knowledgeable assistance from the GBC Help Desk for use of WebCampus. Please go to them for technical assistance. You bear the responsibility for getting the technical aspects of the course to function properly so that you can participate fully. Goals of this course: Students taking this course will have an understanding of covalent bonding, alkanes, alkenes, and alkynes, chirality, alcohols, ethers, benzene, amines, carboxylic acids, polymers, and carbohydrates. Additionally students will have a familiarity with techniques employed in the preparation, separation, and identification of organic compounds. Student Outcomes Outcome Students will understand fundamentals of organic chemistry: electronic structure and covalent bonding, acids and bases, representations of organic molecules and nomenclature, isomers and stereochemistry, delocalized electrons and their effect on stability, reactivity, and pk a, enzymatic catalysis as well as reactions, reactivity, and mechanisms of alkanes, alkenes, alkynes, aromatics, alkyl halides, alcohols, amines, ethers, epoxides, carbonyl compounds, and biological molecules. Students will be able to record experimental procedures and results in a lab notebook in a manner clear enough that experiments may be reproduced and detailed lab reports may be written Students will have technical lab capabilities commensurate with those in a 1-semester organic chemistry course. Examples of techniques may be, but are not limited to simple distillation, extractions, thin layer chromatography, etc. Students will be able to produce scientific lab reports that clearly communicates a scientific experiment and differentiate between the different, distinct parts of the lab report Students will be able to communicate in clear, grammatically correct written English Measurement of this outcome (assessment devices listed) exams, homework, ability to complete labs and write lab reports clearly lab book, lab reports completion of labs, lab reports, lab notebook lab reports lab reports

3 Grading system: Your final grade will be weighted 25% for lab and 75% for lecture. In order to be fair, I will base your final grade on the actual highest total percentage earned by a single person, ie. the class high. This will be done throughout the semester. If you earn 90% of the class high, your grade is A 80-89% of the class high is a B 70-79% of the class high is a C 60-69% of the class high is a D Less than 60% of the class high is an F Your up to the minute grade for this course will be posted on WebCampus in an anonymous spreadsheet. Log on to the WebCampus course and follow the instructions (filed permanently in the announcement area) to view your grade. Extra Credit: There is no extra credit given in this course. Lab portion of your grade: There are 400 total points of lab assignments. Lab quizzes (100), lab notebook (100), and lab reports (200). Each is described in detail below. Lab quizzes: There will be lab quizzes worth a total of 100 points. You are allowed to use your lab notebooks and MSDS binders during these quizzes. (This will encourage you to prepare by copying pertinent information into these places before you come to lab.) The subject matter for these quizzes is the lab we are doing the current day. These quizzes are typical pre-tests. They will test your knowledge of what you are going to do in lab TODAY. This will force you to read and understand the lab BEFORE YOU COME TO CLASS. The quizzes will be designed so that you should easily pass if you have done what you are supposed to do. If you get less than 50% correct on a lab quiz this means that you are a safety hazard and a waste of organic chemistry reagents you will not be allowed to do the lab until you can pass the quiz to my satisfaction (you won t get your quiz points back). This could very likely entail that you come in to the lab at another time in order to make it up. I may ask to see that you have recorded some basic information in your lab notebook as part of a lab quiz (see lab notebook below). Lab notebook: You will be required to keep a lab notebook. It will be worth 100 points. I will check it at the end of the semester most likely during the final. I will attempt to check it during the semester to make sure you are on the right track. Read the description for what should be contained in the lab notebook found on page 8 of the lab textbook. In addition to what our lab textbook suggests you have in the notebook you will also be required to look up the CAS numbers for each reagent/chemical that we use and you need to print out and keep in a separate 3-ring binder all MSDS (material safety data sheets) for all reagents/chemicals we use. The Sigma-Aldrich safety center is an excellent resource ( You can find the safety info for almost any chemical on this website. This is for your own safety you need to read the MSDS information. Another helpful thing to have in your notebook is a sketch of any complicated glassware apparatus that you will need to set up. Having this completed before lab will help you get started. Note: you may have to amend this sketch but it is good to think about the experiment and have a starting point. You are required to purchase a cloth-bound notebook (composition book) that will be your lab notebook for the semester. I prefer the ones that have graph paper inside.

4 Lab reports: You will be required to write a formal (yet brief) lab report for each completed experiment that we do. The lab report grades will be normalized to 200 points. The lab reports will follow the same format as the lab notebook, yet they will be clearer, neater (typed), and more detailed. I will be specific in the lab literature if I am going to require any additional info in a lab report. Lecture portion of your grade: There are 650 total points of lecture assignments. This includes collected homework (150), exams (400), and the cumulative part of the final exam (100). Each is described below. Collected homework: I will collect and grade homework that is assigned in the schedule. It is due at the beginning of the class period where it is listed in the schedule. Each assignment will be worth 10 points and all the assignments for the semester together will be normalized to 150 points. I will grade the homework by checking it briefly for completion and grading 2 random questions for correctness (the same questions will be selected for every student). It will be graded according to the following rubric: less than half of questions attempted - 0 pts., incomplete but more than half of questions attempted 5 pts., complete 7 pts., complete + 1 random question correct 8 pts., complete + 2 random questions correct 10 pts. Your lowest homework score for the semester will be dropped (this will be done a few weeks before the end). Late homework will not be accepted. Exams and the cumulative final: The exams will be on the days listed in the schedule (unless announced otherwise). They will take the entire period (1 hr. 15 min.) to complete. Each exam will cover the material you have seen since the last exam. The cumulative final will take 2 hrs. and 45 min. to complete. It will have approximately 100 points of new material on it (this is the regular exam part) and 100 points of cumulative material on it. It is difficult to schedule a 3 hour block for a final at GBC. I wanted to put the final on the Friday of finals week but GBC graduation is scheduled for this day something original to this year. We will need to find a time that all can agree upon for a 3 hour exam during the week of the 17 th of May. Polices: Attendance policy: Attendance in lecture is not mandatory. In my experience, attendance correlates positively with passing the course. Lab attendance: If you do not attend a lab you will not be able to do the quiz or lab report thus lowering your grade. Plan on scheduling a make up time. Lecture exam make up policy: In order to be fair to students taking the exams on the assigned days I am extremely restrictive with make ups. You will only be allowed to take a make up if you present a written approved excuse before the next time the class meets. You must take the make up exam before the exam is passed back to the rest of the class, which is usually the next class meeting. There are also other ways of doing make up exams that are sometimes allowed such as assigning more points to later exams or the final. These options are only available for approved written excuses at my discretion. If you have missed an exam or know that you are going to miss one see me ASAP. Other policies: Academic dishonesty will not be tolerated and may result in a failing grade and/or reporting to GBC Administration. The students conduct policy in the current GBC catalog will be enforced. This syllabus is not a contract and is subject to change, without warning or notification, at any time.

5 Schedule: This is a preliminary schedule. I reserve the right to change any part of it. Exam dates will likely not change. But if they do, I will attempt to announce the change one week ahead of time in class and on WebCampus. Date Topics Chapter Homework problems due on this day Lab we are doing this week 1 1/26 introduction, syllabus, basics of bonding, formal charge, drawing structures 1 Lab period #1 Fractional distillation of ethanol Cis- to transisomerization 2 1/28 single, double, and triple bonds orbitals, hybridization, π and σ 1 bonds, polar bonds 3 2/2 acids and bases, pk a, organic acids and bases 2 Ch 1: 31-37, 42, 43, 45, /4 predicting acid-base 2 reactions, structure and pk a, Lewis acids and bases 5 2/9 alkanes: basic nomenclature skeletal structures, physical properties and relation to structure, bond rotation, angle strain, conformers of cycloalkanes 6 2/11 alkenes: nomenclature, 4 structure, cis and trans isomers, the E,Z system 7 2/16 alkenes: stabilities, reactivity, nucleophilic addition, reaction coordinate diagrams 8 2/18 Exam 1 (chapters 1-4) Ch 3: 34-36, 38-46, 51, 52, 54, 55 Ch 4: 19, 21-24, 26, 27, 29, 30, 33, 34, Lab period #2 Thin-layer chromatographic analysis of drug components 3 Ch 2: Lab period #3 4 Lab period #4

6 9 2/23 reactions of alkenes and 5 Lab period #5 alkynes: addition of a hydrogen halide predicting products based on carbocation stability (Markovnikov s rule) 10 2/25 reactions of alkenes and 5 alkynes: additions of water and alcohol to alkenes, alkynes (structure, properties, addition reactions), intro to synthesis 11 3/2 cis-trans isomers, 6 Ch 5: Lab period #6 chirality (drawing, naming by R,S system), diastereomers and meso compounds 12 3/4 delocalized electrons: 7 stability and pk a 13 3/9 delocalized electrons: 7 Lab period #7 pk a and absorption of light 14 3/11 Exam 2 (chapter 5-7) Ch 6: 15 3/16 aromaticity, aromatic heterocyclic compounds, nomenclature, reactivity of benzene 16 3/18 electrophilic aromatic substitution, halogenation, nitration, sulfonation, Fiedel- Crafts acylation and alkylation 17 3/30 reactivity of aromatic substituents, nomenclature of disubstituted benzenes, substituents and reactivity of benzene, effect of substituents on orientation Ch 7: 8 Lab period #8 8 Spring Break 8 Ch 8: Lab period #9

7 18 4/1 synthesis of distributed 8 benzenes, the effect of substituents on pk a 19 4/6 S N 2 and S N 1 reactions of 9 Ch 8: Lab period #10 alkyl halides 20 4/8 elimination reactions of 9 alkyl halides 21 4/13 alcohols and amines 10 Ch 9: Lab period # /15 ethers and epoxides /20 Exam 3 (chapter 8-10) Ch 10: Lab period #12 Synthesis of salicylic acid from wintergreen oil 24 4/22 nucleophilic acyl 11 substitution reactions, relative reactivities of carboxylic acids, acyl chlorides 25 4/27 esters and ester hydrolysis, reactions of carboxylic acids and esters, amides 11 Lab period # /29 aldehydes and ketones, nomenclature, reactivities 12 Ch 11: 27 5/4 reactions of carbonyl compounds 12 Lab period # /6 reactions and reactivity at the α-carbon of a carbonyl, keto-enol tautomerization 13 Ch 12: 29 5/11 selected enzymatic mechanisms, the reason 17 Lab period #15 for selected vitamins 30 5/13 the chemistry of drug discovery TBA 3 hour cumulative final (chapters 11-13, 17, and 21 plus cumulative material) 21 Ch 13: Ch 17: no labs this week Americans with Disabilities Act (ADA) Statement: Great Basin College is committed to providing equal educational opportunities to qualified students with disabilities in accordance with state and federal laws and regulations, including the Americans with Disabilities Act of 1990 and Section 504 of the Rehabilitation Act of A qualified student must furnish current verification of disability. The Director of Services for Students with Disabilities (Julie G. Byrnes) will assist

8 qualified students with disabilities in securing the appropriate and reasonable accommodations, auxiliary aids and services. For more information or further assistance, please call