Question

Observe the following reaction \[ \mathrm{C_8H_8O} \;(X) \xrightarrow{Y} Z \] Aromatic compound \(X\) gives both iodoform and 2,4-DNP tests. Product \(Z\) liberates \(\mathrm{CO_2}\) with \(\mathrm{NaHCO_3}\) solution. Identify the set(s) in which \(Y\) is correctly represented from the following. \[ \begin{aligned} \text{I. }&\mathrm{Zn-Hg/HCl;\ KMnO_4/OH^-;\ H_3O^+} \text{II. }&\mathrm{KMnO_4/OH^-;\ H_3O^+} \text{III. }&\mathrm{LiAlH_4;\ H_2O} \end{aligned} \] The correct answer is

• A. I, II only
• B. I, III only
• C. II, III only
• D. I only

Hint:

An aromatic methyl ketone \[ \boxed{\mathrm{ArCOCH_3}} \] gives both the \[ \boxed{\text{Iodoform test}} \] and the \[ \boxed{\text{2,4-DNP test}.} \] Strong oxidation with \[ \boxed{\mathrm{KMnO_4}} \] converts the side chain into \[ \boxed{\mathrm{ArCOOH}.} \]

Answer 1

The Correct Option is A