Syllabus for CHEM 241 Organic Chemistry I, 3CR, Great Basin College Instructor: David Freistroffer Office: Lundberg 109 (in the fishbowl) Phone: 753-2018, but please use email for fastest possible response Email: davidf@gwmail.gbcnv.edu Office Hours: Mon. 4:00-6:00PM, Tues. and Thurs. 2:30-4:00PM, or by appointment Course Description: Intensive introduction to the theory of carbon chemistry with particular emphasis on understanding the relationship between the structure and behavior of organic molecules. Prerequisite: CHEM 122 Corequisite: CHEM 241L A Note on Transferring this Course: This organic chemistry series is designed to transfer to just about any institution in the USA. I have separated out the lab portion of this course to add flexibility in transferring it. Please come talk to me if you plan on transferring this class. Required Text: John McMurry, Organic Chemistry with Biological Applications, Second Edition, 2011, Brooks Cole, ISBN: 0495391441. Optional materials: organic chemistry model set (Prentice Hall version is the best) Method of Instruction: Lecture Course Goals: An understanding of first-semester organic chemistry commensurate with what is studied by lifescience majors. This includes, but is not limited to: structure and bonding, acids and bases, stereochemistry, and the chemistry, reactions and nomenclature of alkanes, alkenes, alkynes, and aromatic compounds. Use of Computers in this Course: Computers will be used for accessing assignments and reading your grades on WebCampus as well as communication and announcements. Computer will be used extensively for writing lab reports. During a break in the first lab (or after the first lab) I will give you a tour of the computer system I have set up for this course. You will learn to use the de facto professional organic chemistry drawing program as part of this course. Grading System for this Course: There are 600 points possible in this class. Exams (4) are worth 100 points each and the cumulative part of the final exam is worth and additional 100 points. Homework will be collected approximately weekly (see course schedule). It is worth 100 points total for the semester.
In order to be fair, I will base your lecture grade on the actual highest total number of points earned by a single person in lecture, ie. the class high. Grades are according to: 90% of the class high A <90% and 80% of the class high B <80% and 70% of the class high C <70% and 60% of the class high D <60% of the class high F Your up to the minute grade in the course will be posted on WebCampus in an anonymous spreadsheet. Log on to the WebCampus course and follow the instructions to view your grade. Lecture Exams: will consist mainly of organic chemistry problems. There will be short sections of essays and other types of questions worth up to 25% of the exam. There are three lecture exams during the semester, each takes 1 hour, 15 minutes to complete. The last exam (exam 4 + cumulative final) is 2 hours and 45 minutes long. It is a combination of 100 points worth of new material and 100 points of cumulative (comprehensive review) material. This exam will be scheduled during the lab period of finals week you must attend the exam at this time you have been warned. Collected : I will collect and grade that is 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 100 points. I will grade the 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 score for the semester will be dropped (this will be done a few weeks before the end). Late will not be accepted. Extra Credit: There is no extra credit given in this course. Lecture Exam Makeup Policy: In order to be fair to students taking the exams on the days I am extremely restrictive with makeups. You will only be allowed to take a makeup if you present a written approved excuse before the next time the class meets. You must take the makeup exam before the exam is passed back to the rest of the class, which is usually the next class. There are also other ways of doing makeup 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. Attendance Policy: Attendance in lecture is not mandatory.
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. Course Objectives, Outcomes, and Assessment of Outcomes Objective Outcome (students will ) Assessment of this Outcome An understanding of structure and bonding in organic molecules An understanding of organic acids and bases An understanding of stereochemistry in organic chemistry An understanding of conformations of organic molecules An understanding of alkanes, alkenes, alkynes, and aromatic compounds understand and be able to apply principles of bonding in organic molecules, including VSEPR theory, valence bond theory, hybrid orbitals, and molecular orbital theory understand and be able to apply principles of organic acids and bases, including pk a, the Brønstead-Lowry definition, and the Lewis definition. They should also be able to predict relative acid and base strengths for organic molecules and the basis for relative pk a. understand stereochemistry of organic molecules and be able to name stereoisomers (cis, trans, R, S, E, Z, etc) know and be able to apply conformations of alkanes, cycloalkanes, monosubstituted cyclohexanes, disubstituted cyclohexanes, polycyclic molecules, and ring strain know nomenclature, reactivity, and reactions of alkanes, cycloalkanes, alkenes, alkynes, and aromatic compounds 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 1973. A qualified student must furnish current verification of disability. The Director of Services for Students with Disabilities (Julie G. Byrnes) will assist qualified students with disabilities in securing the appropriate and reasonable accommodations, auxiliary aids and services. For more information or further assistance, please call 775.753.2271. Course Schedule (subject to change) class 1 1/24 introduction to syllabus, course, and organic 1.1-1.7 chemistry, review of valence bond theory (sp 3, etc) 2 1/26 Bonding: continued review of valence bond theory, 1.8-1.12
class review of molecular orbital theory, drawing chemical structures 3 1/31 Acids and bases: review of electronegativity, dipole moments, formal charges, and resonance 4 2/2 Acids and bases: The Brønsted-Lowry definition, acid and base strength (ph and pk a ), predicting acid-base reactions, organic acids and bases, The Lewis definition, noncovalent interactions 5 2/7 Alkanes and their stereochemistry: overview of ochem functional groups, alkanes and isomers, alkyl groups 2.1-2.6 Due: Ch1 (1-20, 22, 24-26, 30, 33, 34, 36, 40, 42, 43, 45-50, 53, 55) 2.7-2.12 3.1-3.3 Due: Ch2 (1-22, 24-26, 29-33, 35-37, 39, 40, 42, 43, 49-51, 53, 54) 3.4-3.5 6 2/9 Alkanes and their stereochemistry: naming alkanes, properties of alkanes 7 2/14 Alkanes and their stereochemistry: conformations of 3.6-3.7 alkanes 8 2/16 Exam 1 Due: Ch 3 () 9 2/21 Cycloalkanes and their stereochemistry: naming 4.1-4.3 cycloalkanes, cis-trans isomers of alkanes, ring strain 10 2/23 Cycloalkanes and their stereochemistry: 4.4-4.6 conformations of cycloalkanes, cyclohexane (conformations and axial and equatorial bonds) 11 2/28 Cycloalkanes and their stereochemistry: conformations of monosubstituted and disubstituted cyclohexanes, conformations of polycyclic molecules 12 3/1 Stereochemistry at tetrahedral centers: an introduction 13 3/6 Stereochemistry at tetrahedral centers: rules for R and S naming, diastereomers, meso compounds, racemic mixtures 14 3/8 Stereochemistry at tetrahedral centers: overview of isomerism, chirality of N, P, and S, prochirality, chirality in practice 4.7-4.9 5.1-5.4 Due: 5.5-5.8 5.9-5.12 15 3/13 Exam 2 Due 16 3/15 An overview of organic reactions: types of reactions, 6.1-6.4 mechanisms, radical reactions, polar reactions 17 3/20 An overview of organic reactions: addition of H 2 O to ethylene, using curved arrow notation in polar reactions, equilibria, rates, and energy changes in 6.5-6.7
class reactions 18 3/22 An overview of organic reactions: describing 6.8-6.11 reactions (bond dissociation energies, energy diagrams and transition states, intermediates), integrating this with biological reactions Spring Break March 26-31 19 4/3 Alkenes and alkynes: introduction, degree of unsaturation, cis- trans- and E- Z-, 20 4/5 Alkenes and alkynes: stability of alkenes, electrophilic 7.5-7.7 addition reactions, Markovnikov s rule 21 4/10 Alkenes and alkynes: carbocation structure and 7.8-7.10 stability, The Hammond postulate, carbocation rearrangements 7.1-7.4 Due: 22 4/12 Exam 3 Due: 23 4/17 The reactions of alkenes and alkynes: elimination reactions of alkenes (halogenations, halohydrins, hydration), reduction of alkenes - hydrogenation 8.1-8.5 24 4/19 The reactions of alkenes and alkynes: oxidation of alkenes (epoxidation, hydroxylation, cleavage to carbonyls), carbine addition to alkenes cyclopropane synthesis, alkene polymers 25 4/24 The reactions of alkenes and alkynes: biological additions of radicals to alkenes, conjugated dienes, Diels-Alder cycloaddition reaction, reactions of alkynes 8.6-8.10 8.10-8.15 26 4/26 Extra day for chapter 8 we will need it* Ch. 8 27 5/1 Aromatic compounds: naming aromatic compounds, structure and stability of benzene, aromaticity (Hückel 4n+2 rule) 9.1-9.4 Due: 28 5/3 Aromatic compounds: polycyclic aromatic compounds, electrophilic aromatic substitution, Friedel-Crafts reaction, substituent effects 29 5/8 Aromatic compounds: nucleophilic aromatic substitution, oxidation and reduction of aromatics, organic synthesis polysubstituted benzenes 9.5-9.8 9.9-9.11 30 5/10 Extra day for chapter 9 we will need it* Ch. 9 31 5/18 Exam 4 comprehensive final combined with exam on chapters 8-9 (during the lab period of finals week) a 3 hour exam NOTE THAT THIS IS A FRIDAY!!!! *Note: the reasons I have included extra days are for schedule flexibility and because semesters in the Nevada system (for 1:15 classes) have a minimum of 28 days, but the number of days can be as many as 30. This allows me to have consistent syllabi. Due: