An unknown enol ether (X) undergoes mild acidic hydrolysis to yield two compounds, (Y) and (Z). Compound (Y) gives a positive Tollens' test but a negative iodoform test. Compound (Z) gives a negative Tollens' test but a positive iodoform test. Which of the following could be the structure of (X)?

Step-by-step solution

Mild acidic hydrolysis of an enol ether yields a carbonyl compound and an alcohol. Compound (Y) gives a positive Tollens' test, so it must be an aldehyde. It gives a negative iodoform test, so it cannot be acetaldehyde ( CH₃CHO ). Thus, (Y) could be an aldehyde like propanal ( CH₃CH₂CHO ). Compound (Z) gives a negative Tollens' test but a positive iodoform test. Since it is formed alongside a carbonyl compound, (Z) must be the alcohol product. Alcohols that give a positive iodoform test have the structure CH₃-CH(OH