Show how each of the following compounds can be converted to benzoic acid. (i) Ethylbenzene (ii) Acetophenone (iii) Bromobenzene (iv) Phenylethene (Styrene)
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Answer:
(i) Ethylbenzene to Benzoic acid
Ethylbenzene reacts with acidic potassium permanganate to give benzoic acid.
(ii) Acetophenone to Benzoic acid
Step 1: Acetophenone is reduced by zinc amalgum and concentrated hydrochloric acid to form ethylbenzene.
Step 2: Ethylbenzene is oxidised by alkaline potassium permanganate to form potassium benzoate.
Step 3: Acid hydrolysis of potassium benzoate gives benzoic acid.
(iii) Chlorobenzene to Benzoic acid
Step 1: Chlorobenzene and methyl chloride reacts with sodium metal in the presence of dry ether to give toluene.
Step 2: Toulene is oxidised by alkaline potassium permanganate to from potassium benzoate.
Step 3: potassium benzoate on acid hydrolysis gives benzoic acid.
(iv) Phenylethene to Benzoic Acid
Phenylethene is oxidised by potassium permanganate in the presence of diluted sulphuric acid to give benzoic acid and carbon dioxide.