Which one of the following reagents is used to carry out the transformation given below?
CH₃(CH₂)₉COOC₂H₅ → CH₃(CH₂)₉CHO
[amp_mcq option1=”DIBAL-H/H₂O” option2=”H₂/Pd-BaSO₄” option3=”SnCl₂/HCl” option4=”LiAlH₄” correct=”option1″]
This question was previously asked in
UPSC Geoscientist – 2023
The transformation involves reducing an ester (CH₃(CH₂)₉COOC₂H₅) to an aldehyde (CH₃(CH₂)₉CHO). Reducing an ester to an aldehyde requires a specific reducing agent that can stop the reduction at the aldehyde stage, as complete reduction of an ester yields a primary alcohol. Diisobutylaluminium hydride (DIBAL-H) is a reducing agent that, when used at low temperatures and in controlled stoichiometric amounts, can selectively reduce esters to aldehydes.
DIBAL-H is a useful reagent for the partial reduction of esters and nitriles to aldehydes.