093099 - Quiz Answer 4cd - Organic Chemistry 354 - September 30, 1999 - Dr. Sundin

Organic Chemistry 354 Quiz - September 30, 1999

4. Compound A, C₈H₁₆, had a carbon-13 nmr spectrum which revealed six different carbon atoms. A reacted with dilute, basic permanganate solution to give a brown-black precipitate. When A was treated with hot, acidic permanganate, two compounds, B, C₃H₆O, and C, C₅H₁₀O₂, were formed. The carbon-13 nmr spectrum of B revealed two different carbon atoms. The carbon-13 nmr spectrum of C revealed three different carbon atoms.: c. Is B a ketone or a carboxylic acid?; d. Is C a ketone or a carboxylic acid?; Oxidation of alkenes with hot, acidic permanganate gives (depending on the number of hydrogen atoms attached to the sp² carbon) ketones, carboxylic acids, and/or carbon dioxide.; B, C₃H₆O, must be a ketone since it has only one oxygen.; C, C₅H₁₀O₂, must be a carboxylic acid since there are two oxygens which weren't there before.