Compound A, composed of C, H, and O, is heated in a 1.00-L flask to 160._C until all of
Chapter 15, Problem 15.109(choose chapter or problem)
Compound A, composed of C, H, and O, is heated in a 1.00-L flask to 160._C until all of the A has vaporized and displaced the air. The flask is then cooled, and 2.48 g of A remains. When 0.500 g of A burns in O2, 0.409 g of H2O and 1.00 g of CO2 are produced. Compound A is not acidic, but it can be oxidized to compound B, which is weakly acidic: 1.000 g of B is neutralized with 33.9 mL of 0.5 M sodium hydroxide. When B is heated to 260_C, it gives off water and forms C, whose solution in CDCl3 (where D is deuterium, 2H) has one peak in its 1H-NMR spectrum. (a) What are the structures of A, B, and C? (b) Compound A is a controlled substance because it is metabolized to the weakly acidic date rape drug GHB, C4H8O3. What are the structure and name of GHB?
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