CHEMISTRY 242 – 601
Spring Semester, 2008
ORGANIC
CHEMISTRY II
University of Pennsylvania
Instructor: William A. Price, Ph.D. price@lasalle.edu
Teaching Assistants: Onur Atasoylu onur@sas.upenn.edu and Mahmud Hussain mhussain@sas.upenn.edu
Class Meetings: Tuesdays, January 22 – April 29, 2007 from 6:30-9:20 PM
Location: David Rittenhouse Labs, A-4.
Texts: T.W. Graham Solomons and Craig B. Fryhle, Organic Chemistry, 9 th Edition, John Wiley & Sons, 2008.
Web sites:
www.wiley.com/college/wileyplus
Course Description
and Objectives:
Chemistry 242 is a course that will build on the foundation that was established in CHM 241. The course will begin with the study of free radical reactions and alcohols and then focus on structure elucidation using mass spectrometry. Visit my LINKS page for good spectroscopy sites. We will then look at conjugated p systems including pericyclic reactions and aromatic (benzene-type) chemistry. The course will continue with examination of structure, preparation, and reactivity of oxygen- and nitrogen-containing functional groups within molecules. The approach used will incorporate orbital analysis (structure), electron distribution and flow (mechanism), reactions, and ultimately synthesis.
The amount of material to be covered is quite large and it will be presented in 15 sessions, thus it is necessary that you keep up with the course lecture to lecture. This is most readily accomplished by reading the appropriate chapter prior to attending class and doing the assigned problems. This way, the material covered in class will seem somewhat familiar (what a great feeling) and will hopefully clarify any questions you might have. Do not hesitate to ask questions in class, after class or during any office hour on line or at La Salle University. Use of the study guide is helpful, but only if you first attempt the problems on your own. We will follow the attached schedule as close as possible. If we begin to deviate substantially, a new schedule will be produced.
Examinations, Quizzes
& Chapter Coverage:
Your grade will be determined by your performance on two examinations, three quizzes and a cumulative final examination. Exams will take place from 7:40-9:10, (regular lecture from 6:30-7:30). Quizzes will take place from 8:10-9:00 (regular lecture from 6:30-8:00). The exam and quiz schedule with probable chapter coverage follows:
| Quiz 1 | due February 12 | CH 10-11 |
| Exam I | March 4 | CH 10-14 |
| Quiz 2 | April 1 | CH 15,16 |
| Exam II | April 22 | CH 15-18 |
| Quiz 3 | due May 6 | CH 19-20 |
Strategy:
As is evident by the ambitious schedule and the fact that we have 14 sessions together, it is important that you keep pace with this course. It is well documented that attempting to cram three weeks of material into a day and a half prior to an exam is an unsuccessful method to studying in this course. I would advise that you print out the Powerpoint slides prior to coming to class. They will be posted by Tuesday afternoon every week (and likely eartlier). Rewriting one’s notes after each lecture is an effective way to reinforce the lecture material and it typically brings questions to the surface. In a three-hour class this will be particularly important. Do all of the suggested problems and practice sheets. Use your Teaching Assistants as well. Attendance will not be taken regularly, but consistent lecture attendance is strongly urged and necessary since examinations reflect my emphasis in class (and absences will be noticed).
Our anticipated schedule for the semester is ambitious. Please make a note of the dates of quizzes and exams.
Adobe Acrobat Reader is needed in order to access handouts.
WORKSHOP PROBLEM SETS
| Workshop Chapter 10 | Workshop Chapters 13, 14 | |
| Workshop Chapter 11 | Workshop Chapter 15 | |
| Workshop Chapter 12 | Workshop Chapter 16 |
Suggested Problems from Solomons 9th edition, handouts and Powerpoint slides:
Chapter 10: Radical Reactions
Free Radical BDE problems / Answers
Chapters 11and 12: Alcohols / Reactions of Alcohols / Ethers and Epoxides
Practice syntheses and mechanisms for CH 11 and 12 / answers
Infrared Spectroscopy and Mass Spectrometry
IR analysis tutor from UCLA
IR problems from University of Illinois, Chicago
IR overview with problems excellent site from Michigan State, good explanations and problems
IR and MS search search database for IR or MS spectra by molecular formula; free from the gov.
Mass spectrometry tutorial from the University of Arizona
IR/mass matching problems - mass spec answers
Nuclear Magnetic Resonance Spectroscopy
NMR powerpoint tutorial L.G. Wade
spin-spin splitting a slide that helps explain the "n+1" rule
Structure Elucidation Workbook very good spectral problems with IR, NMR & mass spec., Notre Dame
answers to "green" combined spectroscopy problems from Notre Dame site (see above)
answers to some yellow combined pectroscopy problems from Notre Dame site
NMR overview site with H-1 and combined H-1/C-13 NMR problems from Central Connecticut State
C-13 NMR tutorial from Wake Forest
H-1 and C-13 problems from Rider College
Spectral problems 10 problems with IR, mass, proton and C-13 NMR, from Carey
7 C4H10O isomers and 7 1H NMR spectra match 'em up
proton and C-13 problems from Franlin & Marshall College
21 IR / proton NMR problems with answers from University of Colorado
Table of proton and C-13 chemical shifts pdf
Chapter 13: Conjugated Systems, Orbital Symmetry
predicting products in unsymmetrical Diels-Alder reactions
Workshop Handout on Diels-Alder Stereochemistry and Regiochemistry
using Lewis acid catalysts with Diels-Alder reactions
Radiosensitizers and Diels Alder reactions
Chapter 14: Aromatic Compounds
M.O.'s of benzene, cyclobutadiene
problems from ch 13-14 / answers
Vioxx Problem try this answer
Chapter 15: Reactions of Aromatic Compounds
activation/deactivation & directing effects
Nucleophilic Aromatic Substitution and Benzyne mechanistic explanations
Chapter 16: Ketones and Aldehydes
nucleophilic addition overview
acetal formation / imine & enamine formation
CH 15-16 practice problems from old exams answers
more CH 15-16 practice / answers
Chapter
22 Carbs and
Nucleic Acids 29 slides Basic
Carbohydrate Overview
Submit your mnemonic device for aldohexose nomenclature
Glycerol + erythromycin thresh the ribs of an Arab on the xylophone with a lynx.
All altruistically glum mannequins gulp identifying galactic talismans.
Any Ads Granting Me Gold Instigate Greedy Thoughts
All alternative gluttons manage gulping idle gallons as a talent.
GET • RAXL
RIBbed ARAbic XYLophone LYnXes
ALLured ALTos GLUmly MANage GULlible IDOl's GALlant TALes
Chapter 17: Alpha Substitutions and Condensations
alkylation via enolate and enamine
Problems from 17 and 22 / Answers
Chapter 18: Carboxylic Acids
carboxylic acids and acid chlorides
Chapter 18: Carboxylic Acid Derivatives
nomenclature some problems answers
Office Hours:
I am available by appointment Monday, Wednesday and Friday from 9:30-11:00 and Friday afternoons from 12:00 to 4:00. To ensure my availability, please be sure to make an appointment. Please take advantage of these times by phone, e-mail or in person to clarify any lecture material (if you are visiting, make sure you have an appointment). I will respond to every e-mail in a reasonable amount of time. Here is my schedule for the semester.
Your final grade will be determined on your total number of earned points relative to those of your colleagues. Point values are likely to change slightly:
2 Exams 300 pts 41%
3 Quizzes 225 pts 31%
Final Exam 200 pts 28%
725 pts 100%