The incorrect method to synthesize benzaldehyde is
- [figure] , CH3MgBr, followed by H3O+
- [figure] , H2, Pd-BaSO4
- [figure] , DIBAL-H, followed by H2O
- [figure] , CrO2Cl2 in CS2, followed by H3O+
Answer
(1) [figure] , CH3MgBr, followed by H3O+
Solution
(1) A Grignard reagent adds to a nitrile; hydrolysis of the imine gives a ketone:
[figure]
The product is acetophenone, not benzaldehyde — incorrect method.
(2) Benzoyl chloride + H2 / Pd-BaSO4 benzaldehyde (Rosenmund reduction) — correct.
(3) Ethyl benzoate + DIBAL-H, then H2O benzaldehyde — correct (as per NCERT, esters are reduced to aldehydes by DIBAL-H).
(4) Toluene + CrO2Cl2 in CS2 chromium complex H3O+ benzaldehyde (Etard reaction) — correct.
Answer: (1)