Austin Peay State University's biennial Science ExpOlympics involves competitive events, activities and demonstrations, and a science bowl competition for regional high school students. The purpose of the APSU Science ExpOlympics is threefold: to show all of the attending high school students that the sciences can be fun and interesting, to challenge those high school students who are already interested in the sciences, and to promote APSU as a potential university for graduating high school students. More than 2000 high school students have attended the Science ExpOlympics program since its inception in 1983. The Science ExpOlympics program has been jointly sponsored by the Biology, Chemistry, Geography and Geology, Industrial Technology, Mathematics and Computer Sciences, Physics, and Psychology departments.
Formation of carbon-carbon bonds is of fundamental importance in the syntheses of a variety of organic compounds, including terpenes and steroids. One of the methods available to produce this transformation is the alkylation of ketones, a reaction that is well documented in the chemical literature (1-4). A survey of experiments in organic laboratory texts and this Journal indicates a void in the area of alkylation reactions of simple ketones. This experiment provides a relatively simple procedure to fill this vacancy in the undergraduate organic chemistry laboratory literature.A variety of bases (5-7) have been used to convert ketones into their corresponding enolate anions that may then undergo an S N 2 alkylation reaction with alkyl halides to produce new carbon-carbon bonds. Potassium triphenylmethide (tritylpotassium, 1) is a useful base in these reactions for several reasons: it is a strong base with a pK a value of 31.5, it is soluble in inert solvents, it reacts quickly to avoid aldol condensations and is not nucleophilic nor a reducing agent, and the red anion of 1 can be used as an indicator to determine when equivalent amounts of base and ketone have reacted to produce the enolate anion and colorless triphenylmethane. KH 1) DMSO/Ar or He (g) 2) (C 6 H5)3CH/DME 3) 40 °C/30 min (C 6 H 5
acetate-acetic acid (1:1) was placed in a hydrogenator bottle, and after platinum oxide (3 mg) was added, the mixture was stirred at 60 °C for 10 h at 1 atm of hydrogen. The catalyst was removed by filtration, the filtrate was concentrated, and the residual solid was recrystallized from acetone to give 23: 5 mg (50%); mp 41-42 °C; mass spectrum, m/e 292 (M+);
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