a) How are the following obtained? i) benzoic acid from ethylbenzene ii) benzaldehyde from toluene b) Complete each synthesis by giving the missing material, reagent or product: i) C₆H₅COCl →H₂/Pd–BaSO₄→ ____ ii), iii) (the two syntheses shown in the figure)(b)(ii)(b)(iii)
Solution
(a)(i)
C6H5C2H5KMnO4/OH−,ΔH+C6H5COOH
(ii) Etard reaction:
C6H5CH3CrO2Cl2/CS2H3O+C6H5CHO
(b)(i)
C6H5COClH2,Pd/BaSO4C6H5CHO
(ii), (iii) Each printed line gives two members of {substrate, reagent, product}; supply the third by the standard transformation shown (hydride reduction → alcohol; oxidation → acid; named reagent → its product).
