Reaction by which benzaldehyde cannot be prepared
- [figure] + CO + HCl in presence of anhydrous AlCl3
- [figure] + Zn/Hg and conc. HCl
- [figure] + CrO2Cl2 in CS2 followed by H3O+
- [figure] + H2 in presence of Pd-BaSO4
Answer
(2) [figure] + Zn/Hg and conc. HCl
Solution
(1) Gattermann–Koch reaction: benzene + CO + HCl (anhydrous AlCl3/CuCl) ⇒ benzaldehyde.
(2) Zn/Hg and conc. HCl is the Clemmensen reagent; it reduces a >C=O group of aldehydes and ketones to >CH2 and does not convert benzoic acid into benzaldehyde.
(3) Etard reaction: toluene + CrO2Cl2 in CS2, then H3O+ ⇒ benzaldehyde.
(4) Rosenmund reduction: benzoyl chloride + H2 / Pd–BaSO4 ⇒ benzaldehyde.
∴ Benzaldehyde cannot be prepared by reaction (2).
Answer: (2)