(a) Compounds B and E are formed when an organic substance A (summary formula C6H12O3) reacts with a sodium hydroxide solution (saponification).
(b) Substance B can be oxidised in a two-step process to a substance C.
(c) Substance C when reacted with bromine yields a substitution product D which can be hydrolysed by the reaction with sodium hydroxide solution to produce a substance E.
(d) Substance E when allowed to react with a stoichiometric amount of hydrochloric acid gives a compound F (40.0 % C, 6.66 % H, the rest is oxygen).
(e) Substance F is an important product of metabolism in biological processes.
(f) Compound F when allowed to stand, splits off one mole of water from two moles of the substance that results in the formation of an unstable compound G.
(g) Substance F can also be obtained from a compound H containing nitrogen, by onestep reaction with nitrous acid. Assuming the quantitative course of the reaction, 4.5 g of substance F are formed from 4.45 g of substance H.
1. Write all equations for the above mentioned chemical reactions.
2. Give structural formulas of the organic compounds A – H.