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An organic compound (A) having molecular formula C9H10O forms an orange red precipitate (B) with 2,4DNP reagent. Compound (A) gives a yellow precipitate (C) when heated in the presence of iodine and NaOH along with a colorless compound (D). (A) does not reduce Tollen’s reagent of Fehling's solution nor does it decolorize bromine water. On drastic oxidation of (A) with chromic acid, a carboxylic acid (E) of molecular formula C7H6O2 is formed.
Deduce the structures of the organic compounds (A) to (E).

Answer
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Hint: We have to know that the molecular formula specifies the numbers of atoms present in the molecule of a chemical substance. And the molecular formula is the same as that of the empirical formula. The molecular formula mainly contains the chemical symbols of the corresponding element and it has numeric subscripts to express the number of atoms present in a molecule. Therefore, the molecular formula will show the actual number of atoms present in a molecule.

Complete answer:
Here the organic compound A is 1phenylpropanone which does not reduce Tollen’s reagent of Fehling's solution nor does it decolorize bromine water. When 1phenylpropanone reacted with 2,4dinitrile phenyl hydrazine, there is a formation of an orange – red precipitate (compound B) and that precipitate is known as, 1(2,4dinitrophenyl) 2(1 phenylpropan2ylidene) hydrazine. And when 1phenylpropanone is treated with iodine and sodium hydroxide, there is a formation of a colorless compound (D) with compound (C). This colorless compound is known as 2phenyl ethanoic acid and compound C is iodoform. By the drastic oxidation of 1phenylpropanone with chromic acid, there is a formation of carboxylic acid (E) with molecular formula C7H6O2 and the compound is benzoic acid. Let’s see the equation,
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Note:
We need to remember that the 1 Phenyl propanone is an organic compound having the chemical formula C9H10O. It is an aryl ketone which does not have any colour. And the 1Phenyl propanone is insoluble in water and soluble in organic solvents and it is used to make other organic compounds. And benzoic acid is a chemical compound with formula C6H5COOH. Benzoic acid is a simple aromatic carboxylic acid.