Chemistry · Aldehyde and Ketones: Nature of carbonyl group, nucleophilic addition to >C=O group, relative reactivities of aldehydes and ketones

Which of the following reagents convert the acid chloride into aldehyde?

Which of the following reagents convert the acid chloride into aldehyde? \( \boldsymbol{C H}_{3}-\boldsymbol{C H}_{2}-\boldsymbol{C H}_{2}-\boldsymbol{C O}-\boldsymbol{C l} \rightarrow \) \( \boldsymbol{C H}_{3}-\boldsymbol{C H}_{2}-\boldsymbol{C H}_{2}-\boldsymbol{C H O} \)

  • A. \( H_{2}, P d, B a S O_{4} \)
  • B. \( \left(C H_{3}-C H_{2}-C H_{2}-C H_{2}\right)_{3} \) SnH
  • C. LiAlH\( _{4} \)
  • D. Nah

Step-by-step solution

Acid chlorides can be reduced to aldehydes via Rosenmund reduction, which uses hydrogen gas with a palladium catalyst on barium sulfate (Pd/BaSO4). This catalyst is poisoned to prevent over-reduction to alcohols. Option A matches this reagent. LiAlH4 (C) reduces acid chlorides to primary alcohols, and NaH (D) is a base, not a reducing agent. Option B, tributyltin hydride, is not typically used for this conversion.
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