The Diels-Alder Reaction Submitted by: Joe Student Partner: Jill Student Date: February 8‚ 2005 TA: Super TA Reaction +OOOxylene140 oCOOO Data Table Reagents MW Grams used Lit. Mp Anthracene 178.23 g/mol 1.023 g 216-218ºC Maleic anhydride 98.06 g/mol 0.497 g 54-56ºC Products MW Grams obtained Lit. Mp Observed Mp Crude product 276.29 g/mol 1.362 g 261-262ºC 260.2-261.3ºC Recryst. Product 276.29 g/mol 1.283 g 261-262ºC 261.3-261.9ºC Results and Discussion Discuss the
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Diels-Alder Reaction Heather Jost Lab Partner: Jasmina Salcinovic CHEM2642L Luise Strange de Soria Georgia Perimeter College September 29‚ 2004 Diels-Alder Reaction Resources: Mayo‚ Pike‚ Trumper‚ Strange de Soria. Microscale Organic Laboratory. New York: John Wiley and Sons‚ 2002. Strange de Soria‚ Luise. “Student Survival Guide”. http://www.gpc.edu/~lstrange/2642lab/survivalguide/grignard2.pdf. 2004. Purpose: The purpose of these experiments
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THEORY: The Diels-Alder cycloaddition reaction was discovered by Otto Diels and Kurt Alder and is very useful in the synthesis of polycyclic compounds. The Diels-Alder reaction can be described as: [4+2] cycloaddition- a diene with 4 π electrons + 2π electrons from the dienophile; a pericyclic concerted reaction- meaning the reaction occurs in a single step (no intermediates) and involves a cyclic redistribution of bonding electrons. In order for a Diels-Alder reaction to take place
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comes to organic chemistry and the synthesis of specific products there is an abundant amount of routes that can be taken and still get you the same result. For the following experiment‚ the main focus is the use of a cycloaddition reaction‚ also known as Diels-Alder. According to the lab manual‚ this reaction consists of the addition of a diene and a dienophile and that the Diels-Alder reaction builds stereospecific ring compounds with ease (Weldegirma 80). The reaction takes place between the two pi
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Formation of Diels-Alder Reactions The Diels-Alder reactions consist of a reversible dienophile and diene all in a one-step reaction initiated by head. These reactions form a six membered ring with at least one pi bond and two sigma bonds‚ making the reaction exothermic. The goal of the first part of these experiments is to make products that have a greater aromatic stabilization. In 1928‚ Otto Paul Hermann Diels and Kurt Alder first documented this type of reaction‚ hence the name Diels-Alder reactions
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Reminder: These notes are meant to supplement‚ not replace‚ the laboratory manual. A Diels-Alder Reaction History and Application: The 1950 Nobel prize in chemistry was awarded to Otto Paul Hermann Diels and Kurt Alder for their breakthrough work on the discovery and development of [4 + 2] cycloaddition reactions i. This set of reactions are enormously useful in the synthesis of six membered rings in a single stepii. These are used in many pharmaceutical applications. Tamiflu® is a drug which
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EXPERIMENT OBJECTIVE The aim of this experiment is synthesize hexaphenylbenzene via an aldol condensation reaction‚ followed by a Diels-Alder [4+2] cycloaddtion. This is final step in the multistep synthesis pathway to form hexaphenylbenzene‚ and uses the products of the previous experiments: benzil and diphenylacetylene REACTION DIAGRAM TABLE OF REAGENTS BENZIL DIBENZYL KETONE TRITON B 40wt% IN METHANOL (1.79 M) TRIETHYLENE GLYCOL TETRAPHENYL-CYCLOPENTA-DIENONE DIPHENYL ACETYLENE
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Lizz Radican Lab 4 2/24/14 The Diels-Alder Reaction: Results and Problems 1.) Table 1: Mass‚ Percent Yield and Melting Points for Diels-Alder Reaction Products. Product Mass (g) Percent Yield Melting Points (°C) Anhydride 8.87 88.2% 164.4-165.8 Dicarboxylic Acid 3.20 71.9% 176.6-180.1 Unknown 1.66 111% 168.7-176.0 2.) See attached calculations. 3.) Table 2: Anhydride Product IR Data: Functional Group or Bond Peak Location(s) (cm-1) Peak Intensity Symmetric
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prepare an endo‚cis-diacid from the synthesis of the bicyclic anhydride (cis-Norbonene-5‚6-endo-dicarboxylic anhydride). The percent yield of the product was calculated and found to be 39.01%. The infrared spectroscopy confirmed the presence of a O-H group with a stretch at 2948.03 1/cm and the presence of C=O with a stretch at 1698.93 1/cm. Melting point determination found the melting point range of the products to be 149.2-164.1 for the bicyclic anhydride and 169.4-179.5 for the endo-cis‚diacid.
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2013 “Reaction Classes and Pericyclic Reactions” ● 4 Lectures ● Recommended Texts: (i) J. March “Advanced Organic Chemistry”‚ p 839‚ `---Edn.‚ Oxford (W); Warren (2) Ch 34‚ 35. Syllabus 1) General principles (a) Reaction classes (i) Heterolytic (ii) Homolytic (iii) Pericyclic (b) Pericyclic Reaction Types 2) Electrocyclic Reactions (a) Definition and examples (b) Stereochemical aspects and the Woodward and Hoffmann rules 3) Cycloaddition Reactions (a) Definition
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