JEE Challenger
More from Aldehydes, Ketones and Carboxylic Acids

Identify Presence of Carboxyl Functional Group in Organic Compounds

The carboxyl functional group (−COOH-\text{COOH}) can be found in which of the following compounds?

Options

A

picric acid

B

barbituric acid

C

ascorbic acid

D

aspirin

Correct

Step-by-Step Solution

To determine which of the given compounds contains a carboxyl functional group (−COOH-\text{COOH}), let us analyze the chemical structure and functional groups present in each option:

  1. Picric acid (2,4,6-trinitrophenol2,4,6\text{-trinitrophenol}):

    • Formula: C6H3N3O7\text{C}_6\text{H}_3\text{N}_3\text{O}_7
    • Structure: It consists of a benzene ring with a phenolic hydroxyl group (−OH-\text{OH}) and three nitro groups (−NO2-\text{NO}_2) attached at positions 2, 4, and 6.
    • It exhibits acidic properties due to the strong electron-withdrawing effect of the three nitro groups, which stabilizes the phenoxide ion, but it does not contain a carboxyl group (−COOH-\text{COOH}).
  2. Barbituric acid (pyrimidine-2,4,6(1H,3H,5H)-trione\text{pyrimidine-2,4,6}(1H, 3H, 5H)\text{-trione}):

    • Formula: C4H4N2O3\text{C}_4\text{H}_4\text{N}_2\text{O}_3
    • Structure: It is a cyclic urea derivative containing cyclic amide (lactam/imide) functional groups.
    • Its acidity is due to the hydrogen atoms on the C−5\text{C}-5 carbon between two carbonyl groups (active methylene group), and it contains no carboxyl group (−COOH-\text{COOH}).
  3. Ascorbic acid (Vitamin C):

    • Formula: C6H8O6\text{C}_6\text{H}_8\text{O}_6
    • Structure: It contains a five-membered lactone ring with an enediol system (−C(OH)=C(OH)−-\text{C(OH)}=\text{C(OH)}-), alcohol hydroxyl groups, and a ester/lactone group.
    • Its acidity stems from the ionization of the hydroxyl group attached to the double bond (enediol system), which is stabilized by resonance. It does not contain a carboxyl group (−COOH-\text{COOH}).
  4. Aspirin (acetylsalicylic acid\text{acetylsalicylic acid} or 2-acetoxybenzoic acid2\text{-acetoxybenzoic acid}):

    • Formula: C9H8O4\text{C}_9\text{H}_8\text{O}_4
    • Structure: It consists of a benzene ring substituted with an ester group (−OCOCH3-\text{OCOCH}_3) and a carboxylic acid group (−COOH-\text{COOH}).
    • Therefore, Aspirin explicitly contains a carboxyl functional group (−COOH-\text{COOH}).

Thus, the correct option is D.