Introduction to Microscale Organic Experiments, 3d Ed..doc...

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Microscale Organic ExperimentsThird EditionN NN(CH3)2HO3SA Laboratory Manual forOrganic Chemistry IIChemistry 2040Ray A. Gross, Jr., Ph.D.Prince George’s Community CollegeFall 20101
PrefaceThe experiments in this manual overlap the topics covered in the second edition of “Organic Chemistry” by Janice G. Smith. They can be conducted in any sequence, but the order of experiments parallels, as closely as possible, the order in which the chapters of Smith’s text are covered in CHM 202, Organic Chemistry II. This manual is the second-semester companion to “Techniques, Spectra and Reactions—A Laboratory Manual for CHM 2010, Organic Chemistry I, To Accompany Smith’s, Organic Chemistry, 2dEdition.” The experiments are designed to minimize the use of chemicals and the subsequent generation of waste while optimizing the use of microscale glassware. This is now known as “Green Chemistry.” Instructors have the option of adding molecular modeling or instrumental analysis of products to any of the experiments.Like the earlier editions of this manual, this edition focuses on well-known and important reactions and syntheses, such as the aldol condensation and Diels-Alder reaction that students are likely to encounter in their follow-on studies in the biological sciences. The discussions have been expanded to include mechanisms of the reactions and related reactions. Some questions accompanying each experiment have been changed. These questions are designed to test a student’s knowledge of the fundamentalprinciples covered during the second-semester organic course. Students who master thiscontent are well prepared for biochemistry, advanced chemistry and related courses. This edition of this manual is not available in a printed form. 2
ORGANIC LAB REPORT FORMATNameR. Gross Lab PartnerS. SinexExpt # 2 Date9/7/101. Purpose.To conduct a Diels-Alder reactionA short, concise statement—not a complete sentence—of what you intend to accomplish.2. Theory. Certain dienes react with double bonds (dieneophiles) to form new 6-membered rings containing one double bond (cyclohexenes)—see Equation 1 below—or triple bonds (the dieneophiles) to form new 6-membered rings containing two non-conjugated double bonds (1,4-cyclohexadienes)—see Equation 2 below. The reaction is concerted and gives high yields. Diels and Alder shared the Nobel Prize for their discovery of the reaction and the demonstration of its utility. The key features of the reaction are: 1) it makes two new carbon-to-carbon single bonds, and 2) it makes 6-membered rings from two acyclic compounds. In this experiment, both reactants are part of ring systems—see Equation 3 below. The diene is cyclopentadiene and the

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