262L_S09_Manual

262L_S09_Manual - Laboratory in Organic Chemistry Chemistry...

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Laboratory in Organic Chemistry Chemistry 262L Spring 2009 Instructor: David G. Jones Edited by: Dr. R. M. Forbis Dr. H. E. Johns Dr. N. J. Pienta Dr. T. N. Sorrell Dr. M. L. Waters Dr. B. N. A. Mbadugha D.G. Jones Department of Chemistry University of North Carolina at Chapel Hill Chapel Hill, NC 27599-3290 1
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Table of Contents Objectives of the Course. ....................................................................................................... 4 Microscale Reactions. ............................................................................................................. 5 Microscale Equipment. ........................................................................................................... 6 Student Information Sheet. .................................................................................................... 8 References to Topics in Organic Chemistry. ....................................................................... 9 The Laboratory Notebook. .................................................................................................... 11 Sample Page of Laboratory Notebook. ............................................................................... 12 Safety. ..................................................................................................................................... 13 Other Assignments in Chemistry Lab. ................................................................................ 14 Laboratory Calculations. ...................................................................................................... 16 Experiment I Separation by Extraction. .......................................... 19 Experiment II Purification of an Unknown by Recrystallization. ................ 23 Experiment III Nucleophilic Substitution: The Synthesis of 2’-Methylphenoxyacetic Acid. ........................................................................ 28 Experiment IV Dehydration of 2-Methylcyclohexanol. ................................ 32 Experiment V A Wittig Reaction: Preparation of a para -methoxycinnamic Acid. ......................................................................... 38 Experiment VI The Oxidation of Isoborneol. ................................................ 41 Experiment VII Preparation of Amides from Carboxylic Acids. .................. 43 Experiment VIII Electrophilic Aromatic Substitution: Nitration of 4-Methylacetanilide. .................................................................... 46 Experiment IX Column Chromatography: Separation of Nitroacetanilides. ............................................................................................ 48 Sample Exam Questions. ............................................................................... 50 2
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IMPORTANT: Chemical Reagents Used In Chem 262L/263L Below is a list of all chemicals, which are used in Chemistry 262L/263L. Material Safety Data Sheets (MSDS) for all of these materials are on file in Morehead Labs Room 302, or may be found at http://siri.org/msds/ . If you are currently pregnant or become pregnant during the semester of this laboratory course, you are encouraged to consult with your personal physician, or contact Dr. Mary Schlegel at Student Health Services (966-2281), to discuss the advisability of continuing this course. acetic acid acetophenone alumina ammonium hydroxide o-anisic acid m-anisic acid p-anisic acid benzoic acid o-chlorobenzoic acid m-chlorobenzoic acid p-chlorobenzoic acid chromic acid (solution) o-cresol dichloromethane diethyl ether ethanol ethyl acetate hexanes iodine isoborneol ligroin magnesium sulfate 4-methylacetanilide 2-methylcyclohexanol 1-methylcyclohexene nitric acid phenyl magnesium bromide Phosphoric acid sodium chloride sodium chloroacetate sodium hydroxide sodium methoxide sulfuric acid thionyl chloride toluene o-toluic acid m-toluic acid p-toluic acid triethyl phosphonoacetate 3
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OBJECTIVES OF THE COURSE The organic chemistry lab is where you will achieve hands-on exposure to many different techniques associated with manipulating organic compounds. Chem 262L/Chem 263L affords the opportunity to experience the reality of the reactions that you have learned in the organic chemistry lecture courses. This laboratory course will introduce you to some of the following techniques as they apply to carrying out organic reactions: Ø column chromatography Ø crystallization Ø distillation Ø extractions Ø gravity filtration Ø reflux Ø sublimation Ø suction filtration Ø thin-layer chromatography In learning these laboratory techniques, you will encounter or perform the following
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262L_S09_Manual - Laboratory in Organic Chemistry Chemistry...

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