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 2214 (Majors) and 2294 (Honors) Spring Semester 2010 Section 001, Monday, 1:00-3:50 PM, BE401

Instructor: D. Dalton , BE342, Telephone 215-204-7138; Facsimile 215-204-1532 e-mail: david.dalton@temple.edu; URL: http://astro.temple.edu/~dalton Office Hours: M 12:00 noon - 1:00 PM and other times by appointment

COURSE DESCRIPTION:

This course is a continuation of the first semester MAJORS (Chem 2213) and HONORS (Chem 2294) microscale laboratory which is prerequisite. 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 may be used in the laboratory.

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

Co-requisite: Chemistry 2292 - Honors Organic Chemistry Lecture OR Chemistry 2212 - Organic Chemistry for Majors Lecture It is presumed that most students will have completed the first semester of Honors Organic Chemistry, or the corresponding Organic Chemistry for Majors 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 an 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 1 GB (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.

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 Monday, 25 January 2010 .

Your Organic Chemistry laboratory is scheduled (in BE 401) 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 bring with them a hard copy of the completed prelab write-up that can be downloaded from the Honors/Majors Section appearing on photon.chem.temple.edu..

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.

At this writing, there are no plans for a "catch-up-make-up" session scheduled. As a result of an absence you will have lost the opportunity to undertake a given experiment and to accumulate points towards your final total and grade. 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. You will note that 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.

Chemistries 2214 and 2294 (January - April 2010)

Week beginning:	Subject	Comments
25 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. Complete Supplement 4 of the Essential Spartan lessons.
1 February	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 WebMO to examine the Diels-Alder Reaction looked at earlier with Spartan. Monday. 1 February is the last day to drop courses without penalty.
8 February	Experiment 11C: Isolation of a Natural Product by Steam distillation: Cinnamaldehyde from Cinnamon, p 213. Diels-Alder workup	Run IR and NMR spectrum of product. Also run IR and NMR spectra of the Diels-Alder adduct from furan and maleic anhydride. Get the mp of the product.
15 February	Experiment 28: Electrophilic Aromatic Substitution: Bromination of Acetanilide to yield 4-Bromoacetanilide. p 330.	What is the best way to characterize this product? IR? NMR? Complete review of stoichiometry and importance of knowing physical properties. Record melting point for 4-Bromoacetanilide.
22 February	Experiment 5A: Reduction of Ketone using a Metal Hydride Reagent	Cyclohexanol. p 133. IR and NMR of reactants and products. Missing bands (peaks) are as valuable as those present (or more so?).
1 March	Experiment 16: Grignard Reaction with a Ketone: Triphenylmethanol p. 246.	Double all ether volumes. Increase Mg mass by x1.5 Do not wash or wet your equipment. You should have put it away clean!
8 March	Spring Holiday	Spring Holiday
15 March	Experiment 34: Hypochlorite Oxidation of Methyl Ketones by the Haloform Reaction.	Substrate will be varied. Experiment 34A, 34B or other, p 362 as experiment is modified. Spectroscopic tools will allow you to identify the reactant and product.
22 March	Experiment 23A: Amide synthesis	Preparation of acetanilide p. 304. IR and NMR spectra of the reactants and products.
29 March	Experiment 24 A & B	Preparation of N-phenylmaleimide. p. 309
5 April	Preparation of Piperonylonitriles from Piperonal (3,4-methylenedioxybenzaldehyde). IR, NMR and mp.	The manuscript (J.M. DeMott, Jr and C.J. Kelley J.Chem.Ed.chem.wisc.edu 2001) Details are available on photon.chem.temple.edu.
12 April	Experiment 20: Aldol Condensation: Dibenzalacetone., p 279	Recrystallize your product. Hand-outs for laboratory practical. Information available on photon.chem.temple.edu IR, NMR and mp.
19 April	Laboratory Practical Examination
26 April	Clean up and check out. Laboratory Written Examination covering both terms.

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, 30 January 2006. After that grace period the "W" grade is only given in accordance with institutional procedure. The procedure to obtain a "W" grade after 2 February 2009 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 a 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 electron 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.