a) CH3COCH3 → CH3CHClCH3
b) CH3CH2CHO → CH3CH2COOCH3
Compound A (C4H10O) reacts with acidified potassium dichromate to produce compound B. When compound B is warmed with Tollens' reagent, a greyish solid is produced. Compound C (C4H8) is formed when it is treated with hot concentrated sulfuric acid. Compound C is known as an unsaturated hydrocarbon and can decolorize bromine water at room temperature. Compound C also reacts with hydrogen chloride to produce compound D (C4H9Cl). Hydrolysis of compound D will form compound E (C4H10O), which does not decolorize acidified potassium permanganate (VII).