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Reactions: Acetylene Preparation of acetylene and the reaction of chlorine with acetylene are demonstrated. An antique carbide lamp is also demonstrated.
Hydration of Acetylene: A 125th AnniversaryDmitry A. Ponomarev and Sergey M. Shevchenko The discovery the hydration of alkynes catalyzed by mercury ions by Mikhail Kucherov made possible industrial production of acetaldehyde from acetylene and had a profound effect on the development of industrial chemistry in the 1920th centuries. Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ.2007, 84, 1725.
Addition Reactions |
Aldehydes / Ketones |
Alkynes |
Catalysis |
Industrial Chemistry |
Reactions
Ozonolysis Problems That Promote Student ReasoningRay A. Gross Jr. The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products. Gross, Ray A., Jr. J. Chem. Educ.2006, 83, 604.
Aldehydes / Ketones |
Alkenes |
Alkynes |
Carboxylic Acids |
Oxidation / Reduction |
Student-Centered Learning
Synthesis of Unsymmetrical Alkynes via the Alkylation of Sodium Acetylides. An Introduction to Synthetic Design for Organic Chemistry StudentsJennifer N. Shepherd and Jason R. Stenzel Teams of students design a microscale synthesis of an unsymmetrical alkyne using commercially available terminal alkynes and alkyl halides and characterize the resulting products using TLC, IR, and 1H NMR spectroscopy. Depending on the chosen reactants, students observe both substitution and elimination products, or in some cases, no reaction at all. Shepherd, Jennifer N.; Stenzel, Jason R. J. Chem. Educ.2006, 83, 425.
Percent YieldEd Vitz, John W. Moore A section of ChemPrime, the Chemical Educations Digital Library's free General Chemistry textbook.
Synthesis
Molecular Models of Products and Reactants from Suzuki and Heck SynthesesWilliam F. Coleman Our Featured Molecules this month come from the paper by Evangelos Aktoudianakis, Elton Chan, Amanda R. Edward, Isabel Jarosz, Vicki Lee, Leo Mui, Sonya S. Thatipamala, and Andrew P. Dicks (1), in which they describe the synthesis of 4-phenylphenol using an aqueous-based Suzuki reaction. The authors describe the various ways in which this reaction addresses concerns of green chemistry, and point out that their product bears structural similarity to two non-steroidal anti-inflammatory drugs (NSAIDs), felbinac and diflunisal. A number of molecules from this paper and its online supplemental material have been added to the Featured Molecules collection. Students will first notice that the aromatic rings in the molecules based on a biphenyl backbone are non-planar, as is the case in biphenyl. If they look carefully at diflunisal, they will notice that the carbon atoms are in a different chemical environment. One way in which to see the effect of these differing environments is to examine the effect of atom charge on the energies of the carbon 1s orbitals. Figure 1 shows this effect using charges and energies from an HF/631-G(d) calculation. A reasonable question to ask students would be to assign each of the data points to the appropriate carbon atom. As an extension of this exercise students could produce similar plots using different computational schemes. Are the results the same; are they parallel. This would be a useful problem when dealing with the tricky question of exactly what is meant by atom charge in electronic structure calculations. Students with more expertise in organic chemistry could explore extending the synthesis of 4-phenylphenol to produce more complex bi- and polyphenyl-based drugs. This may well be the first time that they have seen coupling reactions such as the Suzuki and Heck reactions. Students in introductory and non-science-major courses might well find the NSAIDs to be an interesting group of molecules, and could be asked to find information on the variety of molecules that display the anti-inflammatory properties associated with NSAIDs. Do they find structural similarities? Are there various classes of NSAIDs? Are they familiar with any of these molecules? Have they taken any NSAIDs? If so, for what reason? Is there any controversy about any of the NSAIDs? As with all of the molecules in the Featured Molecules collections, those added this month provide us with a number of ways of showing students the practical relevance of what they sometime see only as lines on a page. Molecules do matter.
Synthesis
Creative Chemistry Volume 04, issue 15 of a series of leaflets covering subjects of interest to students of elementary chemistry distributed in 1929 - 1932.
