As far back as the 16th century, South American Incas
Chapter 22, Problem 22(choose chapter or problem)
As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wöhler in 1862 resulted in the discovery of cocaine, \(\mathrm{C}_{17} \mathrm{H}_{21} \mathrm{NO}_{4}\), as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, \(\mathrm{C}_{9} \mathrm{H}_{15} \mathrm{NO}_{3}\). Oxidation of ecgonine with \(\mathrm{CrO}_{3}\) yields a keto acid that readily loses \(\mathrm{CO}_{2}\) on heating, giving tropinone.
(a) What is a likely structure for the keto acid?
(b) What is a likely structure for ecgonine, neglecting stereochemistry?
(c) What is a likely structure for cocaine, neglecting stereochemistry?
Equation Transcription:
Text Transcription:
C_17H_21NO_4
C_9H_15NO_3
CrO_3
CO_2
H_3C
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