CHEM 232 Elementary Organic Chemistry I

Syllabus
Instructor: Dr. Nicholas Llewellyn Office Location: 300B Noyes Lab Course Times (U.S. Central Time) & Locations:
Course Component Lecture: All Sections Discussion: ADA Discussion: ADB & OL1 Discussion: ADC Time Self-Arranged 8:00 AM 8:50 AM 11:00 AM 11:50 AM 5:00 PM 5:50 PM Day Self-Arranged MWF MWF MWF Location Wiki or iTunes U 100 Noyes Lab Online 100 Noyes Lab

Spring Term, 2012

Email: nmllew@illinois.edu Office Hours: Thursdays 11:00 AM - 1:00 PM

Required Materials: ACE: ACE Organic is an online evaluation system designed specifically for organic chemistry and run locally at the University of Illinois. ACE Organic will be used to administer all practice problems, quizzes, and exams. To register for your free student account, visit https://ace.chem.illinois.edu, click the Register button, and fill in all required information. Be especially careful of your NetID, which is the part of your University of Illinois email address that precedes @illinois.edu and which should be entered in ALL LOWERCASE CHARACTERS. All students must register an ACE Organic account at the above site by Friday, January 20 or risk missing assignment deadlines.

Recommended Materials: Microphone: Students who wish to participate in oral discussion in the online discussion section (ADB/OL1) must use a microphone headset; built-in microphones are not allowed due to disruptive feedback problems. Students without appropriate microphone equipment may participate by text chat only; most students prefer to communicate by text. Appropriate microphone headsets are available in area bookstores, office supply stores, and electronics stores. Organic chemistry is a three-dimensional geometric science. A solid conceptualization of molecular geometry is critical to understanding organic chemistry. The best way to become comfortable with molecular structure and geometry is by building molecules with a molecular modeling kit, such as the Molecular Visions Model Kit (Darling Models, ISBN: 0964883716), available in area bookstores. Any model kit will do. For the benefit of students who want a supplementary text, Organic Chemistry, 4th Edition by Maitland Jones, Jr. and Steven A. Fleming (W. W. Norton) is available in area bookstores in both hardcopy and eBook formats bundled with the Solutions Manual.

Model Kit:

Text:

General Information
Objectives: To study the principles underlying the structure and reactivity of the major classes of organic compounds, and to apply these principles to solve elementary problems in organic chemistry. Upon completing the course, students should be able to analyze simple organic reactions and to predict the outcome of reactions, even ones that have not explicitly been discussed. Course Overview: In this course, the primary content is communicated through pre-recorded webcast videos instead of traditional lectures. Webcasts are bundled by topic into lessons, which will be discussed in interactive online discussion sessions according to the attached calendar. Further discussion of the material will take place online via the asynchronous discussion pages hosted on the course Wiki. Course grades will be based on regular quizzes and examinations administered according to the attached calendar. Course Wiki: Course materials, course calendar, announcements, and asynchronous supplemental discussion boards will be made available through a course Wiki page. Students are expected to regularly monitor the course Wiki for announcements and discussion. Students are expected to address any out-of-class questions about the course material to the appropriate discussion page on the course Wiki; please do not email the instructor or TAs directly with questions related to course content. The course Wiki is accessed at https://wiki.cites.uiuc.edu/wiki/display/CHEM232SP2012/Home using your NetID and Active Directory password. Most students find it convenient to add this Wiki to their Favorites list on the Wiki Dashboard (https://wiki.cites.uiuc.edu/), which allows for easy monitoring of Wiki discussion activity via the Recent Activity sidebar. Personal RSS feeds of discussion activity may also be created from the Wiki Dashboard page. Compass: Compass will be used in this course as the course gradebook. Compass may also be used to distribute student-specific information such as examination room assignments. Compass may be accessed at https://compass.illinois.edu using your NetID and Active Directory password. Lessons (a.k.a Lecture/a.k.a Webcasts): This course consists of 32 material lessons. Each material lesson is composed of a several short, concept-oriented video webcasts (approximately 15-60 minutes per lesson; average around 30 minutes per lesson). Webcasts are available for streaming online (via links found on the course Wiki) or for download to a computer or mobile device (through the course Wiki or via the CHEM 232 iTunes U site at https://itunes.illinois.edu). Students are expected to view the webcasts for each lesson prior to the scheduled discussion of that lesson. Familiarity with the content of each lesson will be assumed; students should not expect a re-lecture of the lesson content in the discussion sessions.

Discussion: The material presented in the webcast lessons will be discussed in interactive face-to-face or online discussion sessions according to the attached calendar. Face-to-face discussions will be held in locations listed on the front of this syllabus. Online discussions will be held through Elluminate Live! via the link provided on the course Wiki home page and each individual lesson page. Participation in online discussion requires a web-capable computer running a current version of Java and a high-speed internet connection; a microphone headset is required for oral communication with the instructor; students without a headset will be restricted to text chat only (most students prefer text chat). To test the Elluminate Live! environment, visit http://www.elluminate.com and click on the Support tab. Click Configuration Room on the next page, and grant permission to run the Java applet. You should end up in a webconferencing room with an Attendees list with users named Test ###. If not, you may need to update your computer's Java installation. The majority of discussion time is devoted to developing problem-solving and critical-thinking skills with reference to the practice problems for each lesson. Attendance in discussion is not required or recorded (except for merit students), but it is strongly recommended that students participate in the live discussion sessions for any material they feel they do not fully understand. All online discussions will be recorded and archived for later viewing online by any student (regardless of their registered discussion section). Supplemental Instruction (SI): Supplemental Instruction provides additional opportunities for discussion of the course material. SI sessions are led by carefully selected undergraduate students who have previously taken this course with great success. These optional, extra-help sessions are very useful for providing alternative perspectives on the material and proven problem-solving strategies. See the calendar on the course Wiki for times and locations. Other Opportunities for Help: Students are encouraged to collaborate on practice problems and quizzes by posting well thought-out questions and well thought-out responses in the Comments sections of the course Wiki. Questions should be posted as comments to the relevant Wiki page (eg. a general question about molecular orbital diagrams should be addressed to the Lesson 8 page; a question about POTD #3 of Lesson 8 should be addressed to the Lesson 8 POTDs page; etc.) Straight posting of answers and posts begging for answers (e.g., Im totally stuck on #3! Help!!) will not be tolerated, and such posts may be ignored or deleted. The discussion board is a place to work on understanding, not a place to beg for a handout. The instructor and TAs will regularly monitor the Wiki discussion, and will only answer questions posted to the Wiki questions about course content should never be directed to any instructor by email. Only questions about course policies or technical difficulties with ACE Organic may be directed to the instructor by email. Finally, the instructor and TAs will hold regular office hours. TA office hours will be set by the end of the first week of instruction and will be posted to the calendar on the course Wiki.

Coursework
Practice Problems: POTD (Problems of the Day) problem sets will be made available via ACE Organic for each lesson. Practice problems are not graded, but are an important opportunity to familiarize yourself with the tools of this course while also appraising your mastery of the material. Practice problems will also be an important directing component of the discussion sections; therefore, it is strongly recommended that students attempt the relevant practice problems prior to discussion. Students who regularly work the POTDs on time tend to outperform students who do not. Quizzes: A total of 11 quizzes are planned for this semester (see attached schedule). Quizzes are administered through ACE Organic. Quizzes will be opened on ACE Organic on Tuesday evenings and must be submitted by 10:00 PM on the following Monday. Quiz responses may be submitted up to 24 hours past the deadline for half credit. Quiz responses more than 24 hours late will earn no credit. Each quiz question will have three attempts available. Full credit is earned by submitting a correct answer within the permitted number of attempts. No credit is earned for questions that are not attempted or not answered correctly within the allowed number of attempts. Examinations: Two 60-minute midterm examinations and one cumulative two-hour final examination will be administered on campus according to the following schedule: Exam 1: Exam 2: Final: Wednesday, February 22 Wednesday, April 4 8:00 9:00 PM 8:00 9:00 PM

TBD (Final exam schedule set by Registrars Office)

Conflicts with the scheduled exam times must be declared as soon as possible, and not later than two weeks before the scheduled exam date. Exams will be taken either in designated locations on the UIUC campus or (for distance learners) at an approved local proctoring facility. You must bring Photo ID to the exam site. Students must arrive at their examination site promptly at the scheduled time. Students arriving late to the exam will forfeit the lost time and have only up to the scheduled ending time to finish The following materials are permitted during the exam: molecular model kit, basic scientific calculator (no graphing calculators). No other materials (including, but not limited to, music playing devices, headphones, cellular phones, textbooks, course notes, etc.) are permitted. .

Grading
Grades are assigned based on total points earned on quizzes, midterm exams, and the final exam. Possible points for each category of coursework are as follows: Coursework ACE Organic Quizzes Midterm Exam 1 Midterm Exam 2 Final Exam Total Points Possible Points 100 100 100 200 500

All course grades are determined by the criterion grading scale detailed below. In addition, if you meet the criteria stated for the Final Exam Modifier, your course grade could be even higher than what is established by the criterion scale. A) Criterion Grading Scale: The following criterion grading scale will apply to the total points earned from all quizzes, midterm exams, and the final exam. Point totals ending in a decimal value will be rounded to the nearest whole number. Total Points Earned 485-500 465-484 450-464 435-449 415-434 400-414 385-399 365-384 350-364 335-349 315-334 300-314 0-299 Course Grade A+ A AB+ B BC+ C CD+ D DF

B) Final Exam Modifier (a.k.a. The Late Bloomer Policy): For this modifier to be used, students must complete at least 10 of 11 quizzes and sit both midterm exams. A quiz is considered completed if at least 50% of the questions have been attempted not more than 24 hours after the due date (i.e. in time to potentially earn any credit). For students who meet these criteria, their course grade is guaranteed to be no less than the letter grade earned on the final exam according to the criterion grading scale listed in the table below. Whichever grade assignment method gives the student a higher grade will be used. The final exam is not optional under any circumstance. Point totals ending in a decimal value will be rounded to the nearest whole number.

Final Exam Points 194-200 186-193 180-185 174-179 166-173 160-165 154-159 146-153 140-145 134-139 126-133 120-125 0-119 C) Other Modifiers:

Course Grade A+ A AB+ B BC+ C CD+ D DF

The instructor reserves the right to offer additional grade modifiers to the entire class at his discretion. Should additional modifiers be invoked, they will be posted on the course announcements.

Course Policies
Excused Absences: Make-up exams may be offered at the discretion of the instructor in case of an unforeseen, excusable circumstance (e.g. serious illness, hospitalization, death of an immediate family member) consistent with University Policy. Requests for such accommodation should be made directly to the instructor. All requests for accommodation must be followed as soon as possible by a letter from the Office of the Emergency Dean confirming the excuse. Make-up exams must be taken within one week of the missed assignment at a time and place mutually agreeable to the student and the instructor. If a make-up cannot be arranged within this time frame, the assignment may be excused and the students grade prorated, at the discretion of the instructor. Prorating exams is strongly discouraged. Because you have one full week in which to complete the pre-lab quizzes, no extensions to quiz deadlines will be granted. Drop Date: The deadline for undergraduates to withdraw from this course without receiving a grade of W is Friday, March 9 (http://registrar.illinois.edu/registration/deadlines_SPRING2012.html). Course Culture: Students have an obligation to maintain a learning environment that is humane, fair, and respectful. Students are expected to treat one another with civility and decency. Hateful, flaming, and person-directed derogatory comments are unacceptable behavior in this course. Parties involved in such behavior may be immediately expelled from the course at the discretion of the instructor.

Academic Integrity: Students are encouraged to collaborate on quizzes using the discussion threads on the course Wiki (e.g., by discussing concepts and issues or by posting helpful hints without giving away the answer). Straight sharing of answers is not considered collaboration, and is not permitted. Sharing your ACE Organic credentials with any other person is not permitted and, if discovered, will be considered an act of academic misconduct. Examinations are to be performed independently. Article 1 Part 4. Academic Integrity of the Student Code is strictly enforced. All students at the University of Illinois agree to be bound by these regulations regardless of whether they have actually read them. See the following for further information: http://admin.illinois.edu/policy/code/article1_part4_1-401.html If you cheat on any exam, you will receive a failing grade for that exam or for the course at the discretion of the instructor. Sharing your ACE Organic credentials with any other person will be considered academic misconduct, and will result at minimum in a partial letter grade reduction in your final course grade (eg. B becomes B-, B- becomes C+, etc.). Any academic misconduct will be reported to your college in writing. University of Illinois academic integrity policies, as described in the Student Code, will be strictly enforced. Email: All email correspondence related to this course should be sent via your @illinois.edu email account. Email messages received from any other account may not be recognized or may be incorrectly trapped by spam filters. Questions related to the CONTENT of the course should only be addressed in the appropriate discussion thread on the course Wiki, never by email. Please direct questions regarding course policies, procedures, or other concerns to the instructor at nmllew@illinois.edu.

Study Recommendations: This course is substantially self-directed, and may be approached in any way that makes sense to you. The instructor recommends the following workflow to keep up with this fast-moving course: On the day before discussion: o Watch relevant webcast lecture videos. o Attempt relevant POTDs on ACE Organic. o If desired, print discussion slides for note-taking. During discussion: o Attend and participate. Ask questions. Volunteer to solve problems. o Take notes in your preferred format (eg. annotating discussion slides). After discussion: o Address any unresolved questions about the material to the relevant Wiki pages. o Consolidate your notes on the material on paper (for example, in the form of a detailed nested outline). o Attempt relevant Quiz questions and, if you encounter difficulty, address questions to the relevant Wiki pages.

Organic chemistry cannot be memorized. This course is as much a lesson in how to reason logically from sets of (sometimes countervailing) principles as it is about chemistry. An understanding of the processes and principles underlying the chemical phenomena and reactions presented in this course is the best way to understand organic chemistry. Your grasp of the underlying principles will be examined. Remember, you cannot cram for an organic chemistry exam. Organic chemistry is best learned by engaging the material every day and in parts. Waiting until the last minute to study will leave an overwhelming amount of material to be learned in too little time. Consistency and discipline are the keys to success. Online delivery of organic chemistry is a new approach that is intended to offer considerable flexibility to students. This flexibility necessarily places a greater degree of responsibility on the student to choose how to use the available materials and tools. The only requirements of this course are the quizzes and exams; however, it would be ill advised to attempt this course without participating in discussions (both live and through the course Wiki), practice problems, SI sessions and/or independent study groups. Active study is a critical part of success in this course. While all of the subject matter is covered in the lecture/discussion slides, practice problems, etc., just reading things through isn't likely to stick. For myself, active study always meant putting pen to paper and building my own outline of the course in my own words. This sort of studying requires you to take ownership of the material, because you must first digest the concepts before you can write out in your own words how you understand the material. Finally, we are committed to the goal of making CHEM 232 a positive experience for everyone and to improving this course for future generations of students. No course is perfect, and your feedback and suggestions for improvement are always greatly appreciated.

CHEM 232 Spring 2012 Discussion and Quiz Schedule

Lesson --1 2 3 4 5 6 7 8 9 10 11 12 --13 14 15 16 17 18 19 20 21 22 23 --24 25 26 27 28 29 30 31 32 --Discussion Quiz Date # Course Overview 1/20 Period 2 Elements 1/23 1 Building Blocks 1/25 Functional Groups 1/27 Models and Lingo 1/30 Stereochemistry 2/1 2 Resonance 2/3 LCAO 2/6 Molecular Orbital Theory 2/8 3 Frontier Orbital Theory 2/10 Conformations 2/13 Cycloalkanes 2/15 4 Understanding Reactivity 2/17 Exam 1 Review 2/20 Exam 1: Wednesday 2/22 8:00 9:00 PM Structure and Reactivity 2/27 Acid-Base Equilibria 2/29 5 3 Substitution at sp Centers 3/2 3 Elimination at sp Centers 3/5 Stereochemistry of Substitution and Elimination 3/7 6 Carbocation Rearrangements 3/9 Leaving Groups, Nucleophiles, and Ring-Opening 3/12 Addition to Alkenes 3/14 7 Other Electrophilic Additions 3/16 No class Monday 3/26 Addition Stereochemistry 3/28 8 Aromatic Substitution 3/30 Exam 2 Review 4/2 Exam 2: Wednesday 4/4 8:00 9:00 PM More Aromatic Substitution 4/9 Carbonyl Reactivity 4/11 9 Carbonyl & Conjugate Addition 4/13 Acyl Substitution 4/16 Substitution + Addition at the Carbonyl Group 4/18 10 Substitution of C=O 4/20 Reactions at the Carbonyl -Carbon 4/23 Aldol Addition 4/25 11 Claisen Condensation 4/27 Final Exam Review 4/30 Final Exam: TBD (Final exam schedule set by Registrars Office) Topic Quiz Due Date*

1/30

2/6

2/13

2/20

3/5

3/12

3/26

4/2

4/16

4/23

4/30

*Quizzes must be submitted by 10:00 PM on the scheduled due date to receive full credit. Quiz submissions less than 24 hours late may earn half credit. Quiz submissions more than 24 hours late will earn no credit.