Read the passage carefully and answer the questions. Carboxylic acids are the organic compounds which comprise of carboxyl functional group, -COOH. These are generally found in nature, some higher members are known as fatty acids as they occur in natural fats as esters of glycerol. They can be prepared from oxidation of alcohols and aldehydes, hydrolysis of nitriles and amides and Grignard reagents. They are stronger acids than simple phenols and alcohols. but weaker than mineral acids. Substituents affect the acidity of aliphatic and aromatic carboxylic acids. They undergo reactions involving cleavage of -OH and C-OH bond. Carboxylic acids having an alpha hydrogen get halogenated in the presence of red phosphorus to form alpha halo carboxylic acids. The reaction is known as Hell Volhard Zelinsky reaction. Besides these aromatic carboxylic acids undergo electrophilic substitution reactions. They are versatile and are employed in the manufacture of various useful compounds. For example, methanoic acid is used in rubber, textile, dyeing, leather and electroplating industries. Higher fatty acids are used in the manufacture of soaps and detergents. Esters of Benzoic acid are used in perfumery. |
Benzoic acid in the presence of conc. $HNO_3$ and conc. $H_2SO_4$ give major product as |
Ortho-NitroBenzoic acid Para-Nitrobenzoic acid Mixtureof Ortho and para-Nitrobenzoic acid Meta-Nitrobenzoic acid |
Meta-Nitrobenzoic acid |
The correct answer is Option (4) → Meta-Nitrobenzoic acid To answer this, we need to consider the electrophilic substitution of benzoic acid and the directing effect of the –COOH group. Key Concept:The –COOH group (carboxylic acid) is a meta-directing and deactivating group in electrophilic aromatic substitution reactions because it is electron-withdrawing due to resonance and inductive effects. Reaction:When benzoic acid is treated with concentrated HNO₃ and concentrated H₂SO₄, nitration occurs. Since –COOH is meta-directing, the nitro group (–NO₂) gets attached to the meta-position of the benzene ring.
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