PLU (Chem 333)
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Instructor: C. Fryhle
Office: Rieke Science Center 241
Phone: 206-535-8314
Email: fryhle@u.washington.edu
Course Materials:
1) Introduction to Organic Laboratory Techniques - A Microscale Approach, Pavia et al, Saunders, 2nd
ed., 1995
2) Laboratory Notebook, bound quadrilled carbon-less form type.
3) Lab Safety Goggles
| Schedule of Experiments |
|---|
| Laboratory Safety |
| Laboratory Notebooks |
| Samples |
| Weekly Reports |
| Group Formal Reports |
| Laboratory Exam |
| Grading |
| Week | Date | The Experiments | Problems | |
|---|---|---|---|---|
| Sept. 9-13 | Study introductory material in pp. 2-40, especially on Laboratory Safety, pp. 5-21, Read and Study (no lab work) "Introduction to Microscale Laboratory" pp. 42-59 Complete Open Lab Safety Tour | None | ||
| I | Sept. 16-20 | Acetylsalicylic Acid (Exp. 2), Essays: "Aspirin" and "Analgesics" | 3, 7 | |
| II | Sept. 23-27 | TLC Analysis of Drugs (Exp. 4), Essay: "Identification of Drugs" | None | |
| III | Sept. 30-Oct. 4 | Isopentyl Acetate (Exp. 6), and Essay: "Flavors and Fragrances" | 1, 2, 3, 4 | |
| IV | Oct. 7-11 | Essential Oils (Exp. 7), and Essay: "Terpenes and ..." | 1, 4 and NMR, IR Interp. | |
| V | Oct. 14-18 | Stereochemistry - Spearmint and Caraway Oil (Exp. 8, Abbrev.) Essay: "Stereochemical Theory of Odor" Expt. 8, 1-4 | 1, 2, 3, 4 | |
| VI | Oct. 21-24 | Reactivities of Some Alkyl Halides (Exp. 10), | 1, 3 | |
| October 25 | Mid-semester Break | |||
| VII | Oct. 28-Nov. 1 | Synthesis of tert-Pentyl Chloride (Exp. 13) | 1, 2 | |
| VIII | Nov. 4-Nov. 8 | Dehydration of Methylcyclohexanols (Variation on Exp. 15) | 1, 2, 3 | |
| IX | Nov. 11-15 | Synthesis and Reactions of cis-5,6-Norbornene-endo-2,3- dicarboxylic Anhydride (Handout) | Handout | |
| X | Nov. 18-22 | | ||
| XI | Nov. 25-26 | Continue Group Work on Formal Report | ||
| XII | Dec. 2-6 | Grignard Synthesis of Benzoic Acid (Exp. 25B) Essay: "Detection of Alcohol: The Breathalyzer" | 1, 5 | |
| XIII | Dec. 9-13 | |||
A sample of a published paper will be provided illustrating the prescribed layout and style for your paper.
Copyright 1996, Craig B. Fryhle
The Lab Notebook:
Your notebook should be a complete and continuously updated diary or journal for your work in the laboratory. Your notebook is the only place where notes about your laboratory work should be kept, and it should be a thorough record of your work. A stranger with approximately your level of training should be able to read your notebook and repeat your work without any additional assistance, and obtain similar results to your own. In research and industrial situations, a laboratory notebook is a legal document that is signed daily by the author and frequently by a witness. You should ascribe corresponding importance to your laboratory notebook.
Format for Lab Notes:
Your notebook format should be basically that described in Pavia et al., pp. 22-29. The Pavia model as well as a few additional required sections are listed by the headings below. Be sure to begin the notebook with the Table of Contents, Safety and Hazard Information, and List of Abbreviations pages specified above.
Prelab Portion
Date
Title
Reference (e.g., Pavia et al., Exp. X, pp. YY-ZZ)
Goal or Purpose (brief)
Main Reaction [balanced equation(s), including likely side reactions] (Note that this section might not be appropriate for non-preparative experiments.)
Table of Relevant Physical Constants or "Reaction Table" Format - MW, mp or bp, density (for liquids), planned weights and moles, actual amounts and moles (filled in after experiment is begun), and ratio of molar equivalents.
Separation Scheme (Usually a flow chart - not a written duplicate of the planned lab procedure copied from the book. - Be concise but complete.)
HAZARDS (of the chemicals and/or the procedures)
In addition to the lab manual, you will need to consult the Material Safety Data Sheets (MSDS's) available in the Open Lab. Recurring hazards and safety considerations can be documented once in the preliminary notebook pages described above, and simply referenced in the prelab as being noted there.
and initialed by the instructor on duty before the Stockroom
will be allowed to issue you your equipment.]
In-lab Portion
In-lab Notes, Data, and Observations
- Written continuously during the lab period documenting your work in your notebook as you do the work, not at some later time or date. Your notes should be sufficient for someone else to duplicate your work, though not necessarily written in perfect prose.
Calculations
Conclusions
- Brief statement or restatement of key results and conclusions. Editorial comments such as "I think the experiment went well.", etc., are not appropriate.
Date of Completion
Your Signature
Reaction Products
Products requiring further work at a later time should be stored in a labeled vial and given to the stockroom assistants for storage. Final products should be labeled as specified on p. 29 of Pavia, et al, with the addition of the date, tare weight of the container and experiment number, and turned in to the stockroom with the specification that they are to be placed in the "To Be Graded" box for the organic lab. Weekly Reports
The completed lab notes for each experiment, consisting of your work from the prelab through the completed exercises, are due by 6:00 PM on the Monday of the week following a given experiment. Place either the original or carbon-less form copy (so long as it is legible) of your lab notes in the appropriate wooden box in the Open Laboratory. Notebook Spot Checks
In addition, individual lab notebooks will be subject to an unannounced on-the-spot grading once during the semester. This evaluation will be worth 40 points and will be used to assess whether the attributes of notebook style specified above are being incorporated.
The Formal Report
The period of November 18-26 is set aside for collaborative preparation of a formal written laboratory report about one of the previously conducted experiments. The formal report will be due December 2. Some guidelines for the report are as follows:
Title
Authors Names
Affiliation (Course and Institution address)
Abstract
Introduction
Results and Discussion
Experimental Section
Literature References
Group Structure
The four individuals in the group should each take responsibility for one of the following portions of the paper, and then work together to make the paper a cohesive, well-written whole.
The grade for each member of the group will be strongly influenced by the contribution of all the group members, as follows. 80% of the grade for the paper will be the same for all members of the group. Each of the four sections delineated below will be worth 20 points and the score for each section will be summed to achieve 80% of the total. The remaining 20 points of each individual's total score (out of a possible 100) will be calculated by adding again the score for their individual section of the paper.
Collaboration within the group is strongly encouraged, indeed essential. The fundamental thrust of the paper should be agreed upon initially by the group as a whole and relevant data shared. Then, individual group members should prepare drafts of their specific section of the paper. Drafts should then be shared within the group and constructive feedback returned in a timely fashion to the author of each section. All group members should assist with critiquing all sections of the paper. The author of each section should revise their drafts as appropriate, and again solicit feedback from the group. The group should then polish the assembled sections into a finished, very high quality paper, again working through multiple drafts when necessary.
Expectations for the finished paper are very high both in terms of the quality of writing and the level of scientific analysis and literature documentation. You are encouraged to use the library and all other resources available.
The formal report should be typed, double-spaced, and approximately 4-10 pages in length. Be concise, complete, and sure that the paper reads in a logical progression of topics and information.
A variety of computer resources are available for your use in preparing the formal report, including programs for drawing chemical structures and importing them into text documents. See the Organic Chemistry Tool Kit for links and information about some of these. Take advantage of the Computer User Rooms on campus (e.g. in the University Center).
The Formal Report is due on December 2First Individual Title, Abstract, notation and format of references 20%
Second Individual Introduction 20%
Third Individual Results and Discussion 20%
Fourth Individual Experimental Section 20%
Individual Score Individual Section
Added Again20%
Laboratory Final Exam
A Final Exam for the Organic Chemistry Laboratory (Chem 333) will be self-administered in the Open Labduring the final week of the semester. The exam will be worth 60 points and will cover understanding of organic laboratory techniques, procedures, methods for product analysis, and general laboratory practices. The lab final will be a closed-book test, taken under the spirit of academic honesty, and overseen by the Open Laboratory Faculty Supervisors.
Grading
10 Weekly Reports (40 points each) 400 Points
Notebook Spot Check 40 Points
Formal Report 100 Points
Lab Final Exam 60 Points
Late reports of all types will be penalized by 10% per day (maximum of half off).
University Policy
If you need course adaptations of accommodations because of a disability, if you have emergency medical
information to share with me, or if you need special arrangements in case the building must be evacuated, please make an
appointment with me as soon as possible (Rieke 241, x8314). Students are also reminded that they are responsible for notifying
instructors of any conditions that may impair their academic performance. Without advance warning, such difficulties can not be
used later as the basis for requesting make-up course work or reconsideration of grades.
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