Organic Lab Manual 2007-08

Organic Lab Manual 2007-08 - ORGANIC CHEMISTRY LABORATORY...

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1 ORGANIC CHEMISTRY LABORATORY MANUAL 2007-2008 Organic Division Department of Chemistry University of Cincinnati
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2 TABLE OF CONTENTS Introduction ................................................................................................................................ 4 Getting Started ....................................................................................................... 4 Laboratory Notebooks, Protocols, Reports ...................................................................... 5 Preliminary Issues Prior to Starting the First Experiment .............................................. 7 Samples of Lab Notebook Layout .................................................................................. 8 Theoretical and Percent Yields ................................................................................ 21 Grading Policies ........................................................................................................ 21 Experiments ................................................................................................................................ 22 Recrystallization and Melting Point . ............................................................................... 22 UltraMicro Boiling Point ............................................................................................ 25 Thin Layer Chromatography . ........................................................................................... 26 Fractional Distillation and HPLC Analysis .................................................................... 28 Extraction .................................................................................................................... 30 Column Chromatography ............................................................................................ 32 Kinetics .................................................................................................................... 34 Chemiluminescence . ....................................................................................................... 39 Isolation of a Natural Product ................................................................................ 43 Oxidation .................................................................................................................... 45 Reduction .................................................................................................................... 46 Identification of an Unknown via Spectroscopy ....................................................... 48 Grignard .................................................................................................................... 49 Esterification . ................................................................................................................... 52 Modified Wittig ........................................................................................................ 53 Polymerization ........................................................................................................ 56 Hexaphenylbenzene Sequence ................................................................................ 58 Bromination of E-Stilbene ................................................................................ 58 Diphenylacetylene ............................................................................................ 58 Benzoin Condensation ................................................................................ 59 Benzil . ................................................................................................................... 59 Tetraphenylcyclopentadienone .................................................................... 60 Hexaphenylbenzene . ........................................................................................... 60 Friedel-Crafts Acylation; Acetylferrocene .................................................................... 64 An Experiment in Photchromism ................................................................................. 67
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3 A Research Project ......................................................................................................... 71 Checking-In Procedure .......................................................................................................... 74 Checking-Out Procedure .......................................................................................................... 75 Grading Schemes ...................................................................................................................... 76
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4 Introduction Welcome to Organic Chemistry Laboratory. This Manual contains information for all Organic Chemistry laboratories (15-CHEM-211, 212, 213, 352 and 353). Your Syllabus (found on Blackboard) will refer you to the pertinent pages in this Manual, for each experiment you will perform. Some of the experiments will be outlined in this Manual or you will be referred to the experiment in your Mayo et al text. . In addition, there will be references to the Zubrick book, helpful hints, experimental changes and the questions you need to answer for each experiment (either in the Manual or specific questions in Mayo). Both the Mayo book and Zubrick are on Reserve in the Chemistry-Biology Library (503 Rieveschl). You are responsible for all information in the Manual and the information in any references from this Manual. Getting Started in the Microscale Organic Laboratory Mayo: Chapter 1 Please read the material in the reference above, for which you are responsible. Safety Mayo: Chapter 2 Zubrick Chapter 1 Our major goal is to keep you safe during your laboratory experience. Please read the chapters on safety carefully. When you are in your lab, make note of the location of safety showers, eye washes and fire extinguishers. No tolerance will be shown to students who violate the safety rules. You will be asked to leave the lab for the day, with no make-up other than time during your own lab period. In addition to the rules given in the Mayo book, please adhere to the following You must wear OSHA approved GOGGLES, (not lab glasses). If you forget yours, we have a few available for $3.00, non-refundable rental. You have a 3 minute grace period after arrival in the lab to have your GOGGLES on your eyes. They are to remain so, until you are on your way out the door.
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This note was uploaded on 04/08/2008 for the course CHEM 211-213 taught by Professor Lieberman during the Fall '08 term at University of Cincinnati.

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Organic Lab Manual 2007-08 - ORGANIC CHEMISTRY LABORATORY...

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