| Prof. Irvin J. Levy Lecture: MWF, 9:00am-12:00pm Laboratory: T/Th, 9:00am-12:30pm |
There is excitement, adventure and challenge and there
can be great art in organic synthesis. - R.B. Woodward |
TEXTS


1. Organic Chemistry, 7th ed. upgrade, Graham Solomons & Craig Fryhle
2. The Organic Chem Lab Survival Manual, 5th ed., Zubrick
(Recommended) Study Guide to Organic Chemistry,7th ed. upgrade, Solomons & Fryhle
ADDITIONAL MATERIALS
1. Bound notebook for laboratory
2. Safety goggles as required by Department
3. Protective gloves
COURSE STRUCTURE
Daily effort through reading and problem solving is essential to success in this course. Specific assignments following the enclosed Class Schedule will be given daily. It is expected that the assignment will be completed before the next lecture. Homework will not be collected; however, in order to provide continuing motivation, each lecture will begin with a brief quiz based upon the previous assignment. Self-evaluation of homework will be possible through the use of the Study Guide.
CRITERIA FOR EVALUATION
Two Opportunities will be offered on the dates listed in the enclosed Class Schedule. Make-up opportunities are not available. Two low quiz scores will be dropped when computing the final quiz grade. Make-up quizzes are not available.
Laboratories during the second semester use the techniques introduced during the first semester to develop continued depth of skill in the chemistry laboratory. In particular it is assumed that students are familiar with the use of ground glass chemical apparatus, melting point determination, recrystallization, decolorization, vacuum filtration, simple distillation, fractional distillation, extraction, drying, evaporation, and gas chromatography. Students will be challenged to think critically about their work and to take significant responsibility for planning their use of time in the lab.
Laboratory work will be assessed in the following way. A student is expected to attend all labs (or make-up assignment if missed through excusable absence), properly utilize a laboratory notebook (which will be subject to examination without notice), show evidence of preparation for lab (through lab quizzes, flowcharts, etc.), and strictly adhere to all chemical hygiene rules. It is usually very difficult to make up missed labs, thus it is essential that attendance be very faithful. The lab grade will be decreased by 10% for each nonperformance of the expected standards. After a one time grace period (no penalty), upon violation of a chemical hygiene rule, the student will be asked to leave the lab for the remainder of the class period. This will result in two reductions to the lab grade (chemical hygiene violation, nonexcused absence).
Laboratory notebooks will be critiqued by self-evaluation, peer-evaluation (neither of which will
affect the lab grade) and discussion with the professor which will affect the lab grade.
Additionally, during the last laboratory session, a laboratory exam will be administered. The lab
grade will be determined as follows:
0% - Self-evaluation, Peer-evaluation
67% - Professor's evaluation
33% - Laboratory examination
Overall grades will be computed as follows:
20% - Opportunity #1
20% - Opportunity #2 (ACS standardized final examination)
35% - Quizzes (drop 2 low scores)
25% - Laboratory
Both lecture and laboratory must have passing grades in order for a passing grade in the course.
Please note: The summer course in organic chemistry is an accelerated class which covers the
same material as the normal fall/spring curriculum. This class is an equivalent time commitment to
a full-time job. Between lecture, laboratory, reading and homework problems you should plan to
spend about 40 hours per week working on this class. If you are not able to make this significant
time commitment your final result is likely to be very poor. Please make time to allow for success.
IMPORTANT! The grade assigned at the end of the course is based solely on performance on graded work during the semester. There is no element of the grade which depends on what a student "needs" to receive in the class. Sorry to include something that should be obvious. Believe me, from past experience, it's necessary.
RESOURCES
ChemSketch: All-Purpose Chemical Drawing and Graphics Software download IUPAC Naming Tool download Laboratory Notebook Guidelines handout Calculating limiting reagents and percentage yield handout IUPAC Rules of Nomenclature website Aldrich Chemical Company Search Page website ChemExper Chemical Directory website Acros Chemicals website NIST Chemistry Webbook website
| Date | Chapter | Topic |
|---|---|---|
| M, June 23 | 11 | Alcohols and Ethers |
| W, June 25 | 12 | Oxidation & Reduction of Carbonyl Compounds The Grignard Reaction |
| F, June 27 | 13 | Resonance - Conjugation - Delocalization - Stability |
| M, June 30 | 14 | Aromaticity |
| W, July 2 | 15.1-10 | Reactions of Aromatic Compounds, part 1 |
| Th, July 3 | 15.11-15 | Reactions of Aromatic Compounds, part 2 |
| M, July 7 | --- 16.1-6 | * * * OPPORTUNITY #1 * * * After Opportunity: Aldehydes and Ketones: Synthesis; Nucleophilic addition |
| W, July 9 | 16.7,8,10-14 | Aldehydes and ketones: Wittig reaction; Ammonia addition compounds |
| F, July 11 | 17.1-4 | Enolate Chemistry: Introduction to aldol reaction |
| M, July 14 | 17.5-7,9 | Enolate Chemistry: Modifications to the simple aldol reaction |
| W, July 16 | 18 | Carboxylic acids and their derivatives, part 1 |
| F, July 18 | 18,19 | Carboxylic acids and their derivatives, part 2 Acetoacetic ester synthesis; Malonic estersynthesis |
| M, July 21 | 20.1-8,13 21 | Amines (selected topics) Phenols; Nucleophilic Aromatic Substitution |
| W, July 23 | --- | Catch-up; Directed Study Session |
| F, July 25 | --- | * * * OPPORTUNITY #2 * * * |
Note: Laboratory is preceeded by a mandatory pre-lab lecture. Chapters below refer to reading required from "The Organic Chem Lab Survival Manual" before arriving on the lab day. All handouts must be read before arriving on the lab day. Unannounced lab quizzes may be administered. These quizzes will be graded on a Pass/Fail basis. Passing scores will not affect the final lab grade. Each failing score will reduce the final lab grade by 1/3 of a letter grade.
| Meeting | Chapter | Topic |
|---|---|---|
| June 24 | handout ALL NEW students | New Students ONLY: Introduction to Organic Laboratory Check-in to lockers |
| June 26 | handout pp. 61-62, ch. 9, 10, 22, 23 | Grignard synthesis of triphenylmethanol |
| July 1 | handout | Diels-Alder preparation of endo-norbornene-5,6-dicarboxylic anhydride |
| July 8 | handout | Preparation of p-nitroaniline |
| July 10 | handout | Purification of p-nitroaniline |
| July 15 | handout #1 | Preparation of soap: Large-scale organic synthesis |
| handout #2 | Photochemical preparation of benzopinacol | |
| July 17 | handout | Claisen-Schmidt condensation of dibenzalacetone |
| July 22 | handout | TBA - Stay tuned! |
| July 24 | --- | Laboratory Exam, Check-Out |