Identify the suitable reagent for the following conversion. [figure]
- (i) NaBH4, (ii) H+/H2O
- H2/Pd-BaSO4
- (i) LiAlH4, (ii) H+/H2O
- (i) AlH(iBu)2, (ii) H2O
Answer
(4) (i) AlH(iBu)2, (ii) H2O
Solution
As per NCERT, esters are reduced to aldehydes by diisobutylaluminium hydride (DIBAL-H, AlH(iBu)2) followed by hydrolysis; the reaction stops at the aldehyde stage:
C6H5COOCH3 [(ii) H2O](i) AlH(iBu)2 C6H5CHO + CH3OH
(1) NaBH4 does not reduce esters.
(2) H2/Pd-BaSO4 (Rosenmund reduction) reduces acid chlorides, not esters.
(3) LiAlH4 reduces the ester completely to the primary alcohol, C6H5CH2OH.
Answer: (4)