ORGANIC CHEMISTRY 1 LABORATORY CHEMISTRY 2203 Fall 2011 Syllabus Main Campus Dr.

A L Findeisen Course Coordinator Beury 426B; phone 1-7161 TEMPLE UNIVERSITY OFFICE HOURS: *during and after most labs and by appointment E-MAIL: afindeis@temple.edu

COURSE DESCRIPTION: This course provides an introduction to laboratory techniques in organic chemistry. It is offered in the Fall and Spring semesters and in Summer Session 1. Organic I Chemistry Lab places an emphasis on learning to manipulate equipment and to separate, purify, and characterize organic compounds. The student will learn experimental technique in organic chemistry while working with small amounts of materials. Chemistry 2203 meets for 1 two-hour-fifty-minute session each week during the Fall and Spring semesters, and 2 three-hour periods in Summer Session I. Knowledge of stoichiometry (including determination of limiting reagents), solution preparation, volume measurement, temperature measurement, and the proper use of a balance is assumed. COURSE GOALS are to learn to: 1) 2) 3) 4) Use computer based molecular modeling programs. Work safely in the laboratory. Maintain a notebook. Work effectively with small amounts of material.

Pre-requisite: General Chemistry 1032 and 1034 with a C- or better. Students without these pre-requisites will be deenrolled from the course. Co-requisite: Chemistry 2201 - Organic Chemistry I Lecture. You must register for the lecture course if you are taking the lab course for the first time. TEXTBOOK and SUPPLEMENTAL MATERIALS: 1) Mayo, D W, et al. "Microscale Organic Laboratory . . .", 5th edition, J. Wiley & Sons, New York, 2011. ISBN 978-0-471-21502-8 2) Eye Protection that meets ANSI standards. These are available from the TU Chem Society. 3) "General Safety Guidelines for CST Labs" including the RED release waiver available through the Ritter Annex Student Copy Center. 4) "Student Lab Notebook with Permanent Binding, Hayden-McNeil, ISBN 978 1 930882 00 - 3 5) Downloadable materials found on the course Blackboard page and http://photon.chem.temple.edu SCHEDULING: The first laboratory week will begin on Monday, August 29, 2010. Your daily schedule is presented in this syllabus and on www.blackboard.temple.edu where you can access additional information about each experiment. Information of a general nature can be found at www.temple.edu/chem-help The Organic Chemistry 2203 lab section for which you are registered meets once each week. No credit is awarded for attending a different section. Each student is expected to arrive for their lab on time with a copy of the "pre-lab" write up which is automatically generated by your writing in your notebook since every page generates a copy beneath it. You should be prepared for the quiz that will be given at the beginning of each lab session. By the scheduled end of class, students will have cleaned their bench spaces, returned cleaned equipment as necessary, and submitted in lab observations and conclusions as instructed to their teaching assistant (TA). The timely attention to these responsibilities is required The schedule below is divided into three lab types. There are computerized lab assignments found at http://photon.chem.temple.edu behind the Molecular modeling with the Essential SPARTAN button, wet lab assignments with instructions to be found on Blackboard, and wet labs from your Mayo lab text. For each class, you will first meet in the laboratory room for discussion. There you will have a quiz. On some occasions you will adjourn, with your TA, to the Educational Technology Center where you will learn to work with the molecular modeling program Essential Spartan. This software will be available for your use throughout the entire semester. This software will help you in the Organic Chemistry lecture course. Page 1 of 5

The wet laboratory portion will find you performing bench work, which is more traditional for a lab course. You should plan now on having your "Safety Guidelines for CST Labs" and eye protection (safety glasses or goggles) ready. You will not be permitted in the laboratory unless you wear eye protection! You are expected to consult www.blackboard.temple.edu prior to beginning each labs preparation (i.e. before writing the pre-lab). You can access Blackboard to find comments on many of the labs. The last laboratory session occurs on the last scheduled meeting of the student's section, not including study days or finals. Laboratory Schedule: [There is a new Lab each week.] Date Experiment Aug. 29 Sept 2 An Introduction to Essential Spartan. This lab entails becoming familiar with the software so you can build and manipulate organic molecules. You will build ethane. You can use a flash drive to download the Handouts 1 and 2 from http://photon.chem.temple.edu prior to using the software. Henceforth every Tuesday through the following Monday Sept. 6 - 12 Experiment 4A: Determination of a Partition Coefficient for the System - Benzoic Acid, Methylene Chloride, and Water. See Mayo, p.141. Notice: After you complete the microscale experiment described in the text, it will be repeated, as detailed in the supplement Extraction with Separatory Funnel found on Blackboard that gives instructions for a 25x scale-up for purposes of comparison and in order to learn to use a separatory funnel. The last day to drop is Monday, September 12th. Sept. 13 - 19 Experiment 3B: Fractional Semi-Microscale Distillation. See Mayo, p. 132. We will modify the procedure. You will not measure the refractive index. Use Gas Chromatography (GC) to check the purity. Each student will work with their own Hickmann Still assembly. Each student will collect all first distillation components. Inject these fractions into GC, then inject "re-distilled combined cuts" as directed by their TA to compare purity. Sept. 20 26 Introduction to nomenclature, alcohols and stereochemistry. Follow the instructions titled Alcohol Supplement (Week 1) and Lesson_2_2 at http://photon.chem.temple.edu. Use Essential Spartan to determine electron density diagrams, dipoles, and complete the table provided. Sept. 27 Oct. 3 Introduction to stereochemistry of rings. Use the instructions titled Handout 3 Dimethylcyclohexanes and Other Ring Systems at http://photon.chem.temple.edu and Essential Spartan. Oct. 4 - 10 Properties of alcohols. Follow the procedure Solubility of Alcohols found on Blackboard.

Oct. 11 - 17 Experiment 10: Dehydration of 2-Butanol. See Mayo, p. 184. You will use GC to analyze your product. WARNING: Concentrated sulfuric acid will be used. Note: the gas delivery tube will be modified. Your TA will provide you with the new experimental arrangement. . Oct. 18 - 24 Analysis of dyes. See instructions on Blackboard titled Thin Layer Chromatography.

Last day to withdraw is Tuesday, October 25. Oct. 25 - 31 Mayo, p. 163. Nov. 1 7 Experiment 6: Photochemical Isomerization of an Alkene: cis-1,2-Dibenzoylethylene. See Trinity Spectroscopy (Self paced learning package @ TECH CENTER)

Nov. 8 - 14 Experiment D2: Bromination of trans-Cinnamic Acid: erythro-2,3-Dibromo-3phenylpropanoic Acid. See Mayo p.483 and Experiment D3: An Elimination Reaction with erythro-2,3-Dibromo-3phenylpropanoic Acid: 2 Bromstyrene See Mayo p. 488.. Nov. 15 - 21 Experiment 12: Reductive Hydrogenation of an Olefin. See Mayo, p. 244. Note: substitute 1Decene for 1-Octene. Use the same molar quantities as instructed in the Mayo text. Nov. 22 - 28 Nov. 29 Dec 5 Thanksgiving (Temple time) Clean up and check-out. Written lab final.

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GRADING: You will be judged on your own skills. Thus, all the work in this laboratory unless otherwise instructed is to be done on your own. It is expected that the average section grade will be a B. Course grading is as follows: Laboratory quizzes/computer hand-in ..... 30% Laboratory Notebooks .................... 30% Last lab-written final ................... 30% Technique ............................. 10% Total 100 QUIZZES: At the beginning of every laboratory period, while your TA is looking through your pre-lab write-up, you will be taking a short (ca. 10 min) quiz dealing with the lab you have prepared to do. The quiz may be given about five (5) minutes after the laboratory period is scheduled to start. The sum of all quizzes will account for 30% of your grade There is no make-up for missed quizzes. If you miss a single quiz, then an average score will be recorded based on your usual performance and the sections average for that one missed quiz. If a quiz is given prior to your arrival, it is considered missed. Instructors are asked to wait five minutes before administering the quiz. In general, a single missed quiz should not alter a grade. Students are advised to keep all quizzes to help prepare for the lab written final. NOTEBOOK: Your notebook is to accompany you to lab every meeting. You should be able to perform the wet lab using just the information written in your notebook. To help you know what you are going to do before you begin... 1) You must write in ink in your hardbound (not spiral) notebook while making a carbon copy for yourself what you anticipate doing in the laboratory before class time. A typical write-up will be found in your Mayo text, p. 4142. Clearly, you will not be able to write-up the results, but you can, and should, indicate quantities of materials to be used (g or mL, mols, and equiv.), what the reaction or procedure is, and how the equipment set-up will appear. See key components of lab experiment write up items", Mayo, p. 40.

2) You will present the original (preliminary write-up) to be examined by your TA before you start the
experiment. If you do not have that material when you come to lab, then you will not be permitted to begin the experiment! Laboratory notebooks will be collected and graded at least twice during the term. Your TA will work out a schedule with your lab section. Dr. Findeisen may ask to see them at any time. 3) The notebook will be brought to every lab so that it can be kept current. It may be collected or reviewed at any time. Your TA may request data at the conclusion of each lab. You will maintain the carbon duplicate to study for the written lab final. Be certain your copy is legible. WRITTEN FINAL: In order to pass the course, your performance of the written lab final must be above a minimum level. The lab written final occurs on the last scheduled meeting of the student's section. The exam is usually a compilation of 10 or more quiz questions that relate to the experiments performed during the semester. One or more questions may include stoichiometry. A minimum grade on the final is expected for those who will receive grades higher than a B+. Students who do not take this final with their section or make an arrangement with Dr. Findeisen MUST negotiate an incomplete contract to avoid receiving an F for the course. The Universitys Disciplinary Code of Conduct will be enforced. TECHNIQUE: Technique will include items such as: 1) being careful to avoid contamination of common reagents, 2) remembering to keep your work area clean, 3) taking care of the equipment including re-hanging automatic delivery pipets, 4) finishing on time, 5) returning equipment to the location found, 6) keeping only originally inventoried drawer items, 7) recapping reagent bottles, etc. The ability of each section to maintain cleanliness around balances, sort paper waste, sharps, and broken glass by placing these items into the proper container might impact your section's average. A penalty may be assessed to your lab score for failure to return your spinvane. 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 eye protection, gloves, and lab coat and that 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. Page 3 of 5

ELECTRONIC DEVICES FORBIDDEN: The use of calculators is prohibited on examinations or quizzes. Also forbidden are PDAs, cell phones, and electronic or paper dictionaries. WITHDRAWALS: Please note that a withdrawal (W) is an institutional procedure, which is not complete until the withdrawal form has been signed and submitted to the Registrar's office. This course is governed by the Temple University Policy (#03.12.12) on Withdrawal. Details may be found at http://policies.temple.edu/getdoc.asp?policy_no=02.10.14. INCOMPLETES: Please note that an Incomplete (I) is only to be given in accord with institutional procedures. An incomplete is not fulfilled until the specific requirements have been met; the appropriate forms signed and submitted. This course is governed by the Temple University Policy (#03.12.13) on Incompletes". Details may be found at http://policies.temple.edu/getdoc.asp?policy_no=02.10.13. ATTENDANCE POLICY: 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, if you lack eye-protection, or if you arrive 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. If you arrive thirty minutes or more late to the lab, you will not have time to do the experiment. Your registration is section-, room- and time-specific. It is expected that you attend the section for which you have been assigned and only perform work to be graded under your TAs supervision. Students who are found in the lab at other times will be asked to leave and will not receive credit for any work completed. There is no provision for a "make up" of a missed quiz or lab. When you return from an absence, come prepared to undertake the laboratory work scheduled for the time noted...not for what you missed! Final totals are checked for individuals who are near grading boundaries and may have missed a quiz GENERAL INFORMATION Recognizing its obligation to your safety and the environment, and noting the general reduction in the scale on which organic reactions are run in industrial research laboratories that has accompanied the revolution in analytical procedures, the Department of Chemistry has obtained funding from the University to convert your Organic Chemistry Laboratory from one that uses relatively large quantities of material and large (or macro scale) equipment to one that uses small quantities of material and small (or microscale) equipment. In the microscale laboratory the reduction in the quantities of materials used is dramatic and, generally, the time required to carry out reactions is also reduced. Your first wet lab will compare the two different scales. Your manipulative skills will be tried. Our earlier experiences with this course 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. This course is designed to allow the interested participant to rapidly develop the skills needed to slice more deeply into organic chemistry than ever before. Attendant benefits are greater confidence and independence in acquired laboratory techniques. RECYCLING: In an attempt to offer the best equipment at your lowest cost, you are instructed to: 1) Return items "to where you found them". If sufficient quantities or the need existed for each student to have their own piece of equipment it will be provided. To reduce costs we recycle equipment. 2) Re-hang the automatic delivery pipets to the funnel racks or filter flasks provided. 3) Dry solid products on watch glasses. Store liquid yields in shell vials and not conical reaction vials. 4) Return conical vials and spin vanes to the TAs grey box.. DISABILITY RESOURCES and SERVICES: Located in 100 Ritter Annex, this Office of Empowerment arranges accommodations and provides information and support in accessing University programs, facilities, and activities for students with 'certified' disabilities. Services include assisting with academic adjustments and accommodations including sign language interpreters, test proctoring, library research, note taking, and reader services. Information on mobility, wheel chair storage, adaptive computing, small equipment loan, specialized scholarship, and career/internship resources is also available. URL - www.temple.edu/disability ; 215.204.1280; TTY at 204.1786; FAX at 204.6794 SUMMARY: This Organic 1 laboratory course, the companion course to CHEM 2201: Organic Chemistry Lecture 1, introduces the practice of organic chemistry in the laboratory. In this first semester course the primary emphasis is on learning basic laboratory techniques such as extraction, recrystallization, fractional distillation, refluxing a reaction, Page 4 of 5

and gas chromatography. Experiments, performed at both the micro- and macroscale, will also include the preparation and reactions of alkanes, alkenes and alcohols. Students will use software to learn molecular model building fundamentals. An attempt has been made to correlate the syllabus topics with those being consider simultaneously in lecture. On behalf of the Departments Organic faculty, Drs. Andrade, Dalton, Davis, Fleming, Hill, Jasmin, Schafmeister, Sieburth, and Williams have agreed to participate in this laboratory experience with you and, on any given day, you may expect to find one of them in your laboratory sometime during the period. This syllabus was prepared 22 August 2011 and before precise lecture syllabus determinations. As a result all information is tentative and subject to change. Visit your BlackboardTM site or www.temple.edu/chem-help for more recent announcements. Questions concerning this syllabus may be addressed to Dr. Findeisen (afindeis@temple.edu) at 215.204.7161 in Beury Hall 426B (northwest) [The remainder of this page is intentionally blank.]

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