LABORATORY_SYLLABUS_Spring

TENTATIVE SYLLABUS FOR SECOND SEMESTER LABORATORY FOR HONORS AND MAJORS ORGANIC CHEMISTRY (Please consult http://photon.chem.temple.edu for revisions from any campus computer.)

CHEMISTRY 194 Spring Semester 2007 Section 001, Monday, 1:40-4:30, BE409 Section 002, Wednesday, 4:40-7:30, BE409

Instructor: D. Dalton , BE340, Telephone 215-204-7138; Facsimile 215-204-1532 e-mail: david.dalton@temple.edu; URL: http://astro.temple.edu/~dalton OR http://www.temple.edu/dalton Office Hours: MWF 9:30-10:30 and other times by appointment

COURSE DESCRIPTION:

This course is a continuation of the first semester MAJORS (C0183) and HONORS (H0194) microscale laboratory. That course is a prerequisite for this one. Additional microscale laboratory techniques in Organic Chemistry are to be learned. As before, this course places emphasis on independent learning. Students are required to plan their experiments, manipulate equipment in order to separate, purify and characterize organic compounds and write reports after each project detailing their laboratory experience. Hands-on use of spectroscopic (IR and NMR) and computational (Spartan and WebMO) tools are involved. Laptop and benchtop computers are used in the laboratory.

The class meets for one session of two hours and fifty minutes each week.

Co-requisite: Chemistry 192 - Honors Organic Chemistry Lecture OR Chemistry 182 - Organic Chemistry Lecture for Majors [Note: The courses (Chem 182, 192, 184 and 194) require completion of Chemistry 181/183 or Honors Chemistry H0191/H0193.] It is presumed that most students will have completed the first semester of Honors Organic Chemistry, H191/H193 or the corresponding Organic Chemistry for Majors (C181/C183) with the grade of C or better, and that they remain in the Honors Program. Regardless, however, some knowledge of stoichiometry including determination of limiting reagents, the preparation of solutions [molarity], and the use of balances for weighing purposes is assumed. Further, the use of the Spartan software, WebMO, and the IR and NMR equipment learned in the first term will be continued. The work this term places a greater emphasis on independent skills each student gains in carrying out synthesis and characterization of organic compounds

Required textbook and supplementary materials:

1). Mayo, D. W., et al. "Microscale Organic Laboratory ..." , 4th edit., J. Wiley & Sons , New York, 2000.
2). Eye Protection that meets ANSI standards
3). A "memory stick" or similar device for downloading/uploading computer materials. At least 128 MB (more is better) will probably suffice.
4). "General Safety Guidelines for CST Labs" including the release waiver**
5). A hardbound composition book for record keeping and some laboratory notes.

I have been informed that this material is available from the Copy Center in Room 601 Conwell Hall. Additional material and reading matter will be placed on the server to be found at http://photon.chem.temple.edu and which can be accessed from any computer ON CAMPUS.

SCHEDULING:

The FIRST LABORATORY DAY IS Wednesday, 17 January 2007 .

Your Organic Chemistry 194 lab is scheduled (in BE 409) for only one meeting per week. Students are expected to arrive on time. During the "wet-lab" portion of the course (vide infra), every student will have submitted (by email to david.dalton@temple.edu a lab write-up with preliminary information in place. This information is due by 5 PM on the day before the laboratory meets. An outline for that write up can be found on http://photon.chem.temple.edu, or, if on campus, by clicking here .

The completed laboratory report is due (by email) on or before noon of the third calendar day following the laboratory

. You should also be prepared for the quiz that begins every lab.

By the scheduled end of every class students will have cleaned their bench spaces and returned all equipment obtained for use that period. The timely attention to these responsibilities will be rewarded. It is anticipated that a schedule will be established so that each individual has time during the laboratory period to utilize IR and/or NMR on reactants and products. The details of the schedule are a function of the class size and will be provided by the second week of class.

Although there will a "catch-up-make-up" session scheduled for the "wet lab" portion of the course at the end of the term, there is no provision for a "make-up" of a missed quiz. As a result of an absence you will have lost the opportunity to accumulate points towards your final total and grade. So, when you return from an absence, come prepared to undertake the laboratory work as scheduled on the syllabus...not for what you missed!

You should plan now on having your "Safety Guidelines for CST Labs" and eye protection. YOU WILL NOT BE PERMITTED TO WORK IN THE LABORATORY UNLESS YOU ARE WEARING EYE PROTECTION AND ARE DRESSED APPROPRIATELY! . Thus, in addition to safety glasses (contact lenses are not to be worn as organic solvents getting between your iris and the lens can damage your eyes) you are also expected to wear sufficient clothing and foot protection so that dropped objects (flasks, pipettes,etc.) will not injure you and you will not be unprotected in the event of accidental spills.

NOTICE Our earlier experiences with microscale courses have taught us that we must tell you that it is critical that you read, outline, and understand the manipulations you are to perform before you come to class. Processes on a small scale occur with rapidity. There is no time to study the book while reactions are taking place. It is for this reason that your are expected to write up what you need before you come to class and open your laptop computer. The preliminary material can be on a memory stick and you will be ready to record what you are doing. Save it to the memory stick for your later write-up. In the same vein, every laboratory period begins with a quiz that asks questions about what you anticipate doing that day in the lab. Having read and understood the material in advance, you will find the quiz straight forward.

Chemistry 194 (January - April 2007)

Week beginning:	Subject	Comments
15 January	Check-in and discussion of policies, grading, safety. Begin the Diels-Alder reaction.	Begin the Diels-Alder reaction between furan and maleic anhydride. Discussion of the spectroscopy and computational tools available and their use in the laboratory and in BE220. A discussion of the use of the material on http:// photon.chem.temple.edu regarding the course and the laboratory notebook.
22 January	Experiment: Check Diels-Alder reaction. Get IR and NMR spectra of maleic anhydride and furan (the starting materials).	Review Spectroscopy problems in Trinity software, use Essential Spartan on Laptops and in BE 220 and WebMO to examine the Diels-Alder Reaction. Monday 29 January is the last day to drop courses without penalty.
29 January	Experiment 28: Electrophilic Aromatic Substitution: Diels-Alder workup	Bromination of acetanilide (N-acetylaniline; N-acetylaminobenzene). Run IR and NMR spectra of starting materials and products. Also run IR and NMR spectra of the Diels-Alder adduct from furan and maleic anhydride.
5 February	Experiment 16: Grignard Reaction	The reaction to produce triphenylmethanol (p.246) is used. THE EQUIPMENT MUST BE FLAME DRIED BUT ALL FLAMES MUST BE EXTINGUISHED BEFORE ETHER IS USED . . Use spectroscopic tools to identify the product.
12 February	Experiment 34: The Haloform Reaction	The hypochlorite oxidation of a ketone. Write a balanced equation for the haloform reaction. The actual methylketone used will NOT be the same for everyone. You must (IR, NMR) make an effort to identify your starting material and product! Experiment 34A, 34B or other, as modified.
19 February	Experiment 22A: The Williamson ether synthesis	See your laboratory text. Synthesis of n-propyl para-tolyl ether. Use IR and NMR to identify product and check against starting materials.
27 February	Experiment 5B: Reduction of a ketone.	A metal hydride reducing agent is used for reduction of 4-tert-butylcyclohexanone to produce cis and trans-4-tert-butylcyclohexanol. Characterize the products and starting materials.
5 March	Spring Break	Enjoy the Holiday!
12 March	Experiment 32: Hypochlorite Oxidation of an Alcohol	Preparation of cyclohexanone.
19 March	Special Experiment Handout	Conversion of piperonal (3,4-methylenedioxybenzaldehyde) into the corresponding nitrile. Adapted from the Journal of Chemical Education.
26 March	Experiments 24A and 24B	The synthesis of N-phenylmaleimide.
2 April	Experiment 20 The Aldol condensation	Preparation of Dibenzalacetone. Recrystallize your product and then run the IR and NMR. Catch-up/Make-up sign-up. Hand out laboratory practical final information
9 April	Catch-up/Make-up	This week there is no laboratory if all laboratory assignements have been completed.
16 April	Laboratory Practical Final Examination
22 April	Check-out	Turn in all spectra and all reports not previously handed in.

GRADING: Generally, it will be possible for the laboratory instructor to determine your laboratory skills. Thus, the work in this laboratory is done on your own.

Laboratory quizzes/computer hand-in.....30% (Each laboratory begins with a quiz. There are no make-up quizzes.)
Laboratory Notebooks..........................30%
Last laboratory quiz...............................30%
Technique* ...........................................10%

Performance on the last quiz above minimum standards is required to pass the course.

*Technique will include items such as being careful to avoid contamination of common reagents, remembering to keep your work area clean, taking care of the equipment including re-hanging automatic delivery pipets, finishing on time, recapping reagent bottles, returning equipment to the location found, keeping only originally inventoried drawer items, etc . The ability of a section to maintain the cleanliness around balances, sorting paper waste, sharps, and broken glass and then placing these items into the proper container, as well as returning stirrer/hot plates and sand baths, will provide a measure for that section's average.

Withdrawal: Students may withdraw from the course without penalty (Grade of "W") any time up to and through Monday, 12 September. After that grace period the "W" grade is only given in accordance with institutional procedure. The procedure to obtain a "W" grade after 12 September is governed by the Temple University Policy (#03.12.12) on Withdrawal. Please click here to view the policy.

Incomplete: Please note that an Incomplete ("I") Grade is only given in accord with institutional procedures. The "I" grade cannot be given until the specific requirements have been met and forms filled out, signed and submitted. This course is governed by the Temple University Policy (#03.12.13) on Incompletes. Please click here to view the policy.

SAFETY REQUIREMENTS: Although the Department is sensitive to the need for demonstrating personal freedom, the laboratory can be a dangerous place for its expression. Therefore, in addition to denying you admission should you refuse to wear eye protection, the Department requires:

1. Long hair be tied back
2. Closed footwear be worn (open-toed shoes/sandals are not acceptable)
3. Scarves, veils, etc. be tied back or removed during the lab.
4. A general understanding that clothing serves as a good barrier between the laboratory environment and skin.

Attendance: Simply stated, you must attend class to perform the experiments.

You will be asked to leave the class if your pre-lab preparation is insufficient, if you do not dress appropriately or lack eye-protection, or arrive late (when there is insufficient time to perform the experiment). Missing more than one quiz and failing to write up a lab may effect your grade.

Course Goals: You will be learning experimental organic chemistry at the microscale level. This means you will be working with very small amounts of materials and may become able to observe and to learn more organic chemistry in two semesters than many previous students learned in nearly two years. Hopefully you will find this laboratory an exciting, interesting and surprisingly pleasant adventure.

The course is structured to assist you develop skills in several areas considered in lecture and the lab.

1. Molecular modeling programs introduced in the first semester will be expanded upon to enable you to construct and manipulate structures considered in lecture or your lab texts.
2. General safety protocols for the laboratory will be enforced.
3. An electronic notebook will be maintained. IR and NMR spectra will be inserted directly into the experiments as they are undertaken.
4. Techniques and microscale organic lab skills will be developed to permit the flexibility of choosing your own scaling sequence without being tied to a prescribed set of quantities.
5. Methods of characterization of organic materials at the microscale will be utilized.
6. Successful completion will provide a foundation from which you can develop an expertise in microscale techniques as well as the confidence gained by mastering any challenging program.