Chapter 21: Problem 498
Compound A of molecular formula \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{~N}_{2} \mathrm{O}_{2}\) reacts with aqueous nitrous acid to give compound \(B\) of formula \(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}_{4}\). Compound B readily loses water on heating to give \(\mathrm{C}, \mathrm{C}_{6} \mathrm{H}_{8} \mathrm{O}_{3}\). Compound A can also react with a solution of bromine and sodium hydroxide in water to give \(\mathrm{D}, \mathrm{C}_{4} \mathrm{H}_{12} \mathrm{~N}_{2}\), which on treatment with nitrous acid and perchloric acid gives methyl ethyl ketone. Write structures of all compounds and the equations involved.