A chemist has 3 beakers, each containing a pure sample of acetone (2-propanone), isopropanol (2-propanol) and propanal. Using chemical techniques, suggest how the chemist may be able to determine which beaker contains which sample. [4]

Brady's reagent is an orange solution of 2,4-dinitrophenylhydrazine which reacts with carbonyl containing functional groups to produce an orange precipitate (2,4-dinitrophenylhydrazone derivative of the carbonyl compound). [1]Isopropanol won't form a precipitate with Brady's reagent, which allows it to be identified. [1]Acetone and propanal do form precipitates with Brady's reagent [1]. Acetone and propanal can be distinguished by: measuring the melting points of the hydrazone precipitates and comparing those with known literature values/adding Tollen's reagent, which produces a silver mirror with the propanal but not with the acetone, as ketones can't be further oxidised by silver cations but aldehydes can be oxidised to carboxylic acids. [1]