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Home/Practice questions/Chemistry
ChemistryOrganic: Aldehydes, Ketones and Carboxylic Acids

Identify the strongest acid

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.

Identify the strongest acid

Answer & explanation+

Correct answer: option 1

The correct answer is Option (1) → Benzoic acid

A carboxylic acid is stronger when its carboxylate ion is more stable. Groups that donate electrons (+I effect, such as alkyl groups) intensify the negative charge on the carboxylate ion and weaken the acid. A phenyl group attached to the carboxyl carbon is sp2 hybridised and withdraws electrons, so it stabilises the anion and strengthens the acid.

  • Benzoic acid, \( \ce{C6H5COOH} \): the phenyl group is directly on the carboxyl carbon, pKa 4.19.

  • Phenylacetic acid, \( \ce{C6H5CH2COOH} \): the electron-withdrawing phenyl group is one carbon further away, so its effect is weaker, pKa 4.31.

  • Acetic acid, \( \ce{CH3COOH} \): the methyl group donates electrons, pKa 4.76.

  • Propanoic acid, \( \ce{CH3CH2COOH} \): the ethyl group donates electrons more strongly, pKa 4.88.

The lowest pKa belongs to benzoic acid, so it is the strongest acid of the four.

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