Question

Identify the correct set(s) in which the reactant and reagent are correctly matched to get \(\mathrm{C_6H_5CHO}\) from the following \[ \begin{aligned} \text{I. }&\mathrm{C_6H_5CN} \;\xrightarrow[\mathrm{H_2O}]{\mathrm{DIBAL\!-\!H}} \text{II. }&\mathrm{C_6H_5COCl} \;\xrightarrow[\mathrm{Pd\!-\!BaSO_4}]{\mathrm{H_2}} \text{III. }&\mathrm{C_6H_5COOC_2H_5} \;\xrightarrow[\mathrm{H_2O}]{\mathrm{DIBAL\!-\!H}} \end{aligned} \] The correct answer is

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

Hint:

DIBAL-H is a selective reducing agent. \[ \boxed{ \begin{aligned} \text{Nitrile} &\rightarrow \text{Aldehyde} \text{Ester} &\rightarrow \text{Aldehyde} \end{aligned} } \] Rosenmund reduction converts \[ \boxed{\text{Acid chloride} \rightarrow \text{Aldehyde}.} \]

Answer 1

The Correct Option is D