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 2213/2923
Fall Semester 2011
Section 001, Monday, 1:00-3:50, BE401

Instructors: Ms. Svitlana Kulyk, email svitlana.kulyk@temple.edu, Laboratory BE 419;

and D. Dalton, BE342, 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


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 (infrared [IR] and nuclear magnetic resonance [ NMR]) and computational (Spartan , WebMO and Trinity Spectroscopy software) tools are involved. 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 2211/2921 - Majors/Honors Organic Chemistry Lecture (Note: Both Chem 2211/2921 and 2213/2923 courses require completion of General Chemistry 1032/1034 or its equivalent with a grade C or better). It is presumed that most students will have completed Honors General Chemistry, 1952/1954, 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 purposes of massing materials) is assumed.
Required textbook and supplementary materials: ** At this writing, these materials are available from the Copy Center in Ritter Annex. 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. The material 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, 29 August 2011 .

Your Organic Chemistry 2213/2923 lab 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 have sent Svitlana an email (svitlana.kulyk@temple.edu) before midnight of the previous day descrbing what they will be doing in the laboratory 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 a lab coat (provided for you in the lab) and foot protection (shoes with "closed toes" 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.


In summary, the pattern of written laboratory work will be as follows: Before the laboratory class, go to http://photon.chem.temple.edu/Organic_Chemistry/Fall_2007/default.htm and down load the appropriate form onto a flash drive or "memory stick" or onto your laptop or desktop computer. Describe what you are going to do, save the description for your own use and forward a copy to Svitlana (svitlana.kulyk@temple.edu). During laboratory class, use the same form to describe what you did. Brevity is important as are details. It is not necessary to write lengthy statements. Obtain IR and NMR data (as appropriate) and add that to the file for the experiment. While the format for accumulating such data may not immediately be suitable for insertion into a written document, use of MSExcel for X/Y plotting and/or other software to prepare graphic files has been successful in the past. After laboratory, write a complete report (to be submitted before the next laboratory period) using materials found on http://photon.chem.temple.edu/Organic_Chemistry/Fall_2009/default.htm

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. Obtain your copy and bring a "memory stick" (flash drive) device 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 a similar editor and allows you more time. You will be assigned a password for our system during the term should you request it. You will also have the use of laptop computers in the laboratory for this purpose.

SCHEDULE FOR THE FIRST THREE WEEKS

Chemistry 2213 and 2923 (August - December 2011)

Week beginning:

Subject

Comments

29 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 USB flash drive. An introduction to WebMO on line. An Introduction to the Chemical Literature (ReaxSys - formerly Beilstein Crossfire - and SciFinder -from the American Chemical Society [ACS]- both of which can be accessed from the campus ONLY: DiscoveryGate and Houben-Weyl Science of Synthesis, accessed from on campus or through a proxy server; and the SigmaAldrich Database , the National Science Digital Library (NSDL), ChemSpider , etc.). An introduction to drawing software, Accelrys Draw , ACDLabs(ChemSketch), etc.

5 September

SPARTAN Supplement #2

Building BUTANE molecule.Measure energy of the conformations of butane. Construct a plot of energy versus dihedral angle.See Louden,5th edit. Cha 2, pp 53-56.

12 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 computer storage device. 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 have noted above that you must have submitted a proposal of what you anticipate doing in the laboratory by email to Svitlana svitlana.kulyk@temple.edu prior to the laboratory period and 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.
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:

SCHEDULE FOR THE LAST ELEVEN WEEKS

Chemistry 2213 and 2923 (September- December 2010)

Week beginning:

Subject

Comments

19 September

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

Submit preliminary write-up online. The plan for the day. Take quiz on the material. You must have read the material through p. 44, the GC DISCUSSION (pp. 55 - 61) and the material on the Honors/Majors Website at http://photon.chem.temple.edu FOR THE EXPERIMENT TODAY!! Examine equipment. Calibrate heating bath (SEE, p. 21 and Fig 3.11) and pipettes (p. 36; 1a, b). [Work with automatic pipette optional; p.37 - 38; Fig.3.31.] Learn to use IR and NMR. Visit Trinity Software. Record data electronically and also in your hardbound (NOT SPIRAL) notebook (if you have one). EMAIL the laboratory results to yourself and to svitlana.kulyk@temple.edu before leaving. Chart output (from the GC's) can be scanned using the scanner in the second floor computer lab (BE 222).

26 September

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

Turn in report for work of 19 September. Submit preliminary write-up online. Take quiz on the new material. Determination of a Partition Coefficient for the System benzoic acid (benzene carboxylic acid), methylene chloride (dichloromethane), and water. NOTICE. After you complete the microscale experiment described in the text, it will be repeated, as per the SUPPLEMENT (found on http://photon.chem.temple.edu 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 dichlormethane (methylene chloride). Learn to use IR and NMR. Visit Trinity Software. Record data electronically and email to yourself and to svitlana.kulyk@temple.edu (and also in your notebook if you have one).

3 October

Experiment 3B Fractional Semi-microscale Distillation.

Turn in report for work of 26 September. Submit preliminary write-up online. 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 in Mayo p 61-67. You will not measure refractive index. Use GC and IR (take NMR spectra of the starting materials) to check the purity. Each student of a pair will work with her/his own Hickmann Still assembly. Each student will collect both first distillation components. Take IR spectrum and then inject these fractions into GC, then reinject "re-distilled combined cuts" as directed by instructor to check purity. Record data electronically and also in your notebook. The gc charts can be scanned using the scanner in the computer laboratory. Email results to yourself and to svitlana.kulyk@temple.edu.

10 October

Experiment 11B: Isolation of caffeine from tea

Turn in report for work of 3 October. Submit preliminary write-up on line. The plan for the day. Take quiz on the material. Read the introduction on Mayo, p 224, then the material beginning in Mayo on p 229. SAVE THE SAMPLE OF CAFFEINE IN A VIAL bearing a label with your name on it and turn it in at the end of the laboratory period. Record data electronically and also in your notebook. Email results to yourself and to svitlana.kulyk@temple.edu .

17 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. (Get IR and NMR data on the alcohol). Record data electronically and in your notebook. Email results to yourself and to svitlana.kulyk@temple.edu .

24 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 483 ff . Record data electronically and also in notebook. Email results to yourself and to svitlana.kulyk@temple.edu .

31 October

Experiment 13: Oxidative Hydroboration of 1-Decene (or 1-Octene)

Turn in report for work of 24 October. Submit preliminary write-up. The plan for the day. Take quiz on the material. 1-Decanol (or 1-octanol) is the product. You must have read the material on Mayo, pp 250 ff before coming to class. Perform the column chromatography and obtain IR and NMR spectra of the starting material and an IR spectrum of the product. Note the differences in IR spectra. Record data electronically and also in notebook. Email results to yourself and to svitlana.kulyk@temple.edu .

7 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 (or n-octane) is the product. See Mayo p 244 ff. GC will be used to determine if the reduction has succeeded. How will you know? IR and NMR spectra of the starting material. Record data electronically and also in notebook. Email results to yourself and to svitlana.kulyk@temple.edu .

14 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).Email results and questions to: svitlana.kulyl@temple.edu .

21 November

Spectroscopy.

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

28 November

Check-out

Last Laboratory Quiz (cumulative). Turn in written notebook if you have one and it will be returned at the final examination (lecture). Turn in electronic notebook.


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 drop this course on or before 13 September 2011 without penalty. Students may withdraw from this course (Grade of "W") any time up to and through Monday, 31 October 2011. The "W" grade is only given in accordance with institutional procedure. The procedure to obtain a "W" grade after 31 October 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.


Academic Honesty: The contents of this section are from Temple University's current Undergraduate Bulletin in the Students Responsibilities part of Responsibilities section. The web address is http://www.temple.edu/bulletin/Responsibilities_rights/responsibilities/responsibilities.shtm#honesty.

Temple University believes strongly in academic honesty and integrity.

Plagiarism and academic cheating are, therefore, prohibited.

The development of independent thought and a respect for the thoughts of others is essential to intellectual growth. So, the prohibition against plagiarism and cheating is intended to foster this independence and respect.

Plagiarism is the unacknowledged use of another person's labor, another person's ideas, another person's words, another person's assistance. Normally, all work done for courses -- papers, examinations, homework exercises, laboratory reports, oral presentations -- is expected to be the individual effort of the student presenting the work. Any assistance must be reported to the instructor. If the work has entailed consulting other resources -- journals, books, or other media --, these resources must be cited appropriately. Everything used from other sources -- suggestions for organization of ideas, ideas themselves, or actual language -- must be cited. Failure to cite borrowed material constitutes plagiarism. Undocumented use of materials from the World Wide Web is also plagiarism.

Academic cheating is, generally, the thwarting or breaking of the general rules of academic work or the specific rules of the individual courses. It includes falsifying data; submitting, without the instructor's approval, work in one course which was done for another; helping others to plagiarize or cheat from one's own or another's work; or actually doing the work of another person. The penalty for academic dishonesty can vary from receiving a reprimand and a failing grade for a particular assignment, to a failing grade in the course, to suspension or expulsion from the University. The penalty varies with the nature of the offense, the individual instructor, the department, and the School or College. Students who believe that they have been unfairly accused may appeal through the School or College's academic grievance procedure.


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.