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

CHEMISTRY 183/193
Fall Semester 2006
Section 001, Monday, 1:40-4:30, BE409
Section 002, Wednesday, 4:40-7:30, BE409
Section 003, Thursday, 12:40-3:30, BE409

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


COURSE DESCRIPTION:

This course provides an introduction to microscale laboratory techniques in Organic Chemistry. It 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. Temple University Students enrolled in this course should access the Honors/Majors server for this course by clicking here from anywhere on campus or, if off campus, by adjusting the proxy of their browser as directed here .

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


Co-requisite: Chemistry 181/191 - Honors/Majors Organic Chemistry Lecture (Note: Both Chem 181/191 and 183/193 courses require completion of General Chemistry 072/074 or its equivalent with a grade C or better. It is presumed that most students will have completed Honors General Chemistry, H092/H094, 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).
Required textbook and supplementary materials: ** These materials are available from the Copy Center in Room 601 Conwell Hall. Plan on purchasing them two days before class so that you will be prepared for lab.

Supplementary material for the Laboratory is available on line at http://photon.chem.temple.edu which can be accessed from any computer ON CAMPUS or, if off campus, by adjusting the proxy of their browser as directed here ..


SCHEDULING:

The FIRST LABORATORY DAY IS MONDAY, 28 August 2005 .

Your Organic Chemistry 193 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 bring with them a carbon copy ("carbon paper" is provided) of the prelab write-up that appears in their respective laboratory notebooks.

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

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!

The schedule below is divided into two portions. The first three classes are different from the last eleven, For the first three, you will be expected to meet in the laboratory room for discussion prior to learning to work with molecular modeling software. Those programs ["Spartan ES" and "WebMO"] will be available for your use throughout the entire semester! The last eleven meetings of the term will be spent in the laboratory to which you are now assigned doing BENCH WORK - more traditional for this course. 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.

As is usual for laboratory work, a written report, describing what you did (and using the appropriate software for drawing reactions and inserting spectra into your report) in the previous week's laboratory is to be turned in at the beginning of each lab. It will be graded and returned to you by the following week.


PART 1

The curriculum for the first three sessions...

The "ESSENTIAL SPARTAN SUPPLEMENT" exercises are available at photon.chem.temple.edu from any terminal on campus or from any location where you can reset the proxy on your browser (directions for accomplishing this are available from Temple University Computer Services for various browsers) and require a TU computer account. Copies are also on sale at the Student Copy Center, 601 Conwell Hall, (with 24 hours notice). Obtain your copy and bring a 3.5" diskette for your next lab meeting.
This class is also required to learn the use of WebMO.

Initially, you are expected to learn to use the graphics editor in WebMO, at your convenience, during the first three weeks of class by going to the commercial website to be found by clicking here . The sixth item down on the left-hand column allows you to access the editor. The eleventh item allows you to participate in lessons! However, this commercial version allows you only two minutes of CPU time when attempting a computation. Our version at Temple uses the same editor and allows you more time. You will be assigned a password for our system during the term. You will also have the use of laptop computers in the laboratory for this purpose.

SCHEDULE FOR THE FIRST THREE WEEKS

Chemistry 193 (August - December 2006

Week beginning:

Subject

Comments

28 August

SPARTAN Supplement #1

Lecture/Demo on an introduction to molecular modeling; Practicing with Spartan; Leaving Spartan. Fundamentals of Molecule Building. Building ethane. Remember your 3.5" diskette A comparison to WebMO.

4 September

SPARTAN Supplement #2

Building BUTANE molecule.Measure energy of the conformations of butane. Construct a plot of energy versus dihedral angle. See Jones, Cha 2, pp 71 ff

11 September

SPARTAN Supplement #3

An introduction to cyclic molecules. Examine the conformers of cyclohexane. Introduce substituents onto cyclic hydrocarbons. Submit your plot of energy vs. dihedral angle. Turn in your calculations of cyclic molecules. Remember your 3.5" diskette. (Jones, Cha 5 pp 191 ff deals with this topic in some detail we will revisit it with Spartan and/or WebMO at the appropriate time). Prepare GASOLINE SUPPLEMENT FOR NEXT WEEK!!


PART 2

The curriculum for the remainder of the semester...

>>> REMEMBER <<<
NO ONE IS PERMITTED IN THE LABORATORY WITHOUT SAFETY EYE WEAR. THERE ARE NO EXCEPTIONS.

WITHOUT YOUR SAFETY GLASSES AND CLOSED SHOES YOU WILL NOT BE PERMITTED TO STAY.


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.

SCHEDULE FOR THE LAST ELEVEN WEEKS

Chemistry 193 (August - December 2005)

Week beginning:

Subject

Comments

18 September

Check-in and GC of Gasoline (Analytical Chemistry: Spectroscopy)

Submit preliminary write-up. The plan for the day. Take quiz on the material. You must have read the material through p. 43, the GC DISCUSSION (pp. 44 - 49) and the material in the SUPPLEMENT FOR THE EXPERIMENT TODAY!! Examine equipment. Calibrate heating bath (SEE, p. 19 and Fig 3.11) and pipettes (p. 26; 1a, b). [Work with automatic pipette optional; p.27 - 28; Fig.3.21.] Learn to use IR and NMR. Visit Trinity Software. Record data electronically and also in notebook.

25 September

Experiment 4A Determination of a Partition Coefficient (Analytical Chemistry: Spectroscopy)

Turn in report for work of 19 September. Submit preliminary write-up. The plan for the day. Take quiz on the material.Determination of a Partition Coefficient for the System Benzoic Acid, Methylene Chloride, and Water. NOTICE. After you complete the microscale experiment described in the text, it will be repeated, as per the SUPPLEMENT on a 50 fold scale-up for purposes of comparison and in order to learn to use a separatory funnel. Use your 10-mL graduated cylinder to collect CH2Cl2. Learn to use IR and NMR. Visit Trinity Software. Record data electronically and also in notebook.

2 October

Experiment 3B Fractional Semi microscale Distillation.

Turn in report for work of 26 September. Submit preliminary write-up. The plan for the day. Take quiz on the material. You will be separating a mixture of cyclohexane (bp 80.7 deg C) and toluene (bp 110 deg C). Procedure on Mayo p 115. You will not measure refractive index. Use GC, IR and NMR to check the purity. Each student of pair will work with her/his own Hickmann Still assembly. Each student will collect both first distillation components. Take IR and NMR spectra Inject these fractions into GC, then reinject "re-distilled combined cuts" as directed by instructor to check purity. Take IR and NMR spectra. Record data electronically and also in notebook.

9 October

Experiment 11B: Isolation of caffeine from tea

Turn in report for work of 3 October. Submit preliminary write-up. The plan for the day. Take quiz on the material.Read the introduction on Mayo, p 199, then the material beginning in Mayo on p 204. SAVE THE SAMPLE OF CAFFEINE IN A LABELED VIAL*** Record data electronically and also in notebook.

16 October

Experiment 9: Dehydration of 2-Butanol

Turn in report for work of 10 October. Submit preliminary write-up. The plan for the day. Take quiz on the material."The butenes". GC needed. WARNING: Concentrated sulfuric acid will be used. Note: the gas delivery tube has been modified. Your instructor will provide you with the modification.*** (NMR). Record data electronically and also in notebook.

23 October

Experiment D2: Bromination of trans-Cinnamic Acid

Turn in report for work of 17 October. Submit preliminary write-up. The plan for the day. Take quiz on the material. Erythro-2,3-dibromo-3-phenylpropanoic acid. Use dichloromethane for recrystallization solvent. Procedures found on Mayo, pp 441 ff and 75, respectively. Record data electronically and also in notebook.

30 October

Experiment 13: Oxidative Hydroboration of 1-Decene

Turn in report for work of 24 October. Submit preliminary write-up. The plan for the day. Take quiz on the material. 1-Decanol is the product. You must have read the material on Mayo, pp 223 ff before coming to class. Perform the column chromatography and obtain an IR and NMR spectrum. Record data electronically and also in notebook.

6 November

Experiment 12: Reductive Hydrogenation of an Olefin

Turn in report for work of 31 October. Submit preliminary write-up. The plan for the day. Take quiz on the material.n-Decane is the product. See Mayo p 218 ff. GC will be used to determine if the reduction has succeeded. How will you know? IR and NMR. Record data electronically and also in notebook.

13 November

Catch-up/Make-up day.

Turn in report for work of 7 November. Students who have not missed any laboratory period should use this time to review Spartan, WebMO, and Trinity (Spectroscopy) Software. Work on WebMO problems from the WebMO webpage (http://www.webmo.net).

20 November

Spectroscopy.

Complete problems on the WebMO webpage (http://www.webmo.net) and the Trinity software

27 November

Check-out

Last Laboratory Quiz (cumulative). Turn in notebook. Your notebook will be returned at the final examination (lecture).


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.

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 o denying you admission should you refuse to wear eye protection, the Department requires:
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.