Quinolines, heterocyclic compounds that contain a pyridine ring fused to a benzene ring
Chapter 20, Problem 35(choose chapter or problem)
Quinolines, heterocyclic compounds that contain a pyridine ring fused to a benzene ring, are commonly synthesized by a method known as the Skraup synthesis, in which aniline reacts with glycerol under acidic conditions. Nitrobenzene is added to the reaction mixture to serve as an oxidizing agent. The fi rst step in the synthesis is the dehydration of glycerol to propenal. CH2 + 2 H2O H2SO4 CH2 CH CH2 CH O CH OH OH OH N glycerol quinoline NH2 NO2 a. What product would be obtained if para -ethylaniline were used instead of aniline? b. What product would be obtained if 3-hexen-2-one were used instead of glycerol? c. What starting materials are needed for the synthesis of 2,7-diethyl-3-methylquinoline?
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