Tossup

This molecule binds to palladium and carbenes to promote cross-couplings as a part of PEPPSI (“pepsi”) catalysts. A reaction that forms this molecule is characterized by imine (“IMM-een”) formation, an aldol (-5[1])condensation, and a Michael addition. A tetrahydro- precursor to this molecule is formed by using an imine as the dienophile (10[1])(“dye-EEN-o-phile”) in the aza-Diels–Alder reaction. A 3-brominated derivative of this molecule binds to a ruthenium ion in third generation Grubbs catalysts. Derivatives of this molecule can be made by condensing carbonyls with ammonia in the Chichibabin (10[1]-5[1])(“chee-chee-BAH-bin”) synthesis. (10[2])A carboxylic acid is attached to the meta position of this molecule in the structure of niacin. (-5[1])This molecule’s (10[1])chlorochromate (10[1])is used (10[1])to (10[1])oxidize (10[2])alcohols (10[2])to carbonyls (10[1])and is abbreviated (10[1])PCC. For 10 points, name this molecule whose aromatic ring (-5[1])consists of five carbons (-5[1])and a nitrogen. ■END■ (10[2]0[8])

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