An organic compound (A) gives violet colour with neutral \(\mathrm{FeCl}_{3}\). It answers Liebermann's test. This compound on catalytic reduction gives (B). The saturated compound (B) on oxidation with \(\mathrm{CrO}_{3}\) gives (C) of molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}\). (C) gives precipitate with 2,4 -dinitrophenylhydrazine. (C) can be obtained by reductive ozonolysis of (D). The other product of reductive ozonolysis, (E), undergoes Cannizzaro reaction with benzaldehyde to give (F) and HCOONa. Answer the following questions. Arrange in order of increasing acidity of (i) (A) (ii) p-nitrophenol (iii) p-methylphenol (iv) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) (a) (iv) \(<(\mathrm{iii})<(\mathrm{i})<(\mathrm{ii})\) (b) \((\mathrm{iv})<(\mathrm{iii})<(\mathrm{ii})<(\mathrm{i})\) (c) \((\mathrm{i})<(\mathrm{iv})<(\mathrm{iii})<(\mathrm{ii})\) (d) (ii) \(<(\mathrm{iv})<(\mathrm{iii})<(\mathrm{i})\)

Step by step solution

01

Identifying the compound (A)

Compound (A) gives a violet color with neutral \(\mathrm{FeCl}_{3}\), and answers Liebermann's test. These properties indicate that (A) is likely a phenolic compound.

02

Determining the acidity of the molecules

Phenolic compounds such as (A) are generally more acidic than alcohols due to the ability of the phenoxide ion to delocalize the negative charge across the aromatic ring. p-nitrophenol and p-methylphenol are also phenolic compounds, and their acidity is affected by the electron-withdrawing or donating properties of their respective substituents. (i) (A) - Phenolic compound (ii) p-nitrophenol - Nitro group is electron-withdrawing, increasing acidity (iii) p-methylphenol - Methyl group is electron-donating, decreasing acidity (iv) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) - This is an alcohol, generally less acidic than phenols

03

Arranging the molecules in order of increasing acidity

Since the nitro group on p-nitrophenol increases its acidity and the methyl group on p-methylphenol decreases its acidity, we can compare them with the other phenolic compound, (A), and the more weakly acidic alcohol, \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\): - \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) (least acidic) - p-methylphenol - (A) - p-nitrophenol (most acidic) This corresponds to option (a) in the given choices: (a) \((\mathrm{iv})<(\mathrm{iii})<(\mathrm{i})<(\mathrm{ii})\)

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