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Chemistry · Ch 12 — Aldehydes, Ketones and Carboxylic Acids

Classification of carboxylic acids

12.2.3

Classification of carboxylic acids

Carboxylic acids are classified as aliphatic or aromatic. ALIPHATIC CARBOXYLIC ACIDS (also called fatty acids) have the -COOH (carboxyl) group bonded to an alkyl group; general formula R-COOH, R = H or alkyl. As with formaldehyde among the aldehydes, there is one exception: formic acid, H-COOH, is still classed as an aliphatic carboxylic acid even though its -COOH is not attached to any carbon at all. Worked examples: acetic acid (CH3-COOH) and propionic acid (CH3-CH2-COOH), both MONOcarboxylic acids (one -COOH group); oxalic acid (HOOC-COOH), a DIcarboxylic acid (two -COOH groups bonded directly to each other); and citric acid (a central carbon bearing an -OH plus three -COOH-bearing arms), a TRIcarboxylic acid. Carboxylic acids are widely distributed in nature, in both plants and animals: L-lactic acid occurs in curd, citric acid in citrus fruit such as lemons, and acetic acid is the key ingredient of vinegar. AROMATIC CARBOXYLIC ACIDS have one or more -COOH groups attached DIRECTLY to the aromatic ring -- e.g. benzoic acid (one ring -COOH) and phthalic acid (two ring -COOH groups, at adjacent/ortho positions, i.e. benzene-1,2-dicarboxylic acid); aspirin (acetyl salicylic acid) is a further example, carrying a ring -COOH plus a ring -OCOCH3 ester group. A 'Remember' box draws an important distinction: if the -COOH group is NOT attached directly to the ring -- e.g. phenylacetic acid, C6H5-C …

Figure 12.2.3aGeneral formula of a carboxylic acid
Fig. 12.2.3a — General formula of a carboxylic acid

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

What this figure shows. A carbonyl carbon doubly bonded to O and singly bonded to -OH and to R (R = H or alkyl), i.e. the general skeletal formula R-COOH for any carboxylic acid, labelled the 'carboxyl functional group' -- the direct carboxylic-acid analogue of the aliphatic-aldehyde and aliphatic-ketone general-formula figures given earlier in 12.2.1 and 12.2.2, now with the -H or -R of a carbony …

Figure 12.2.3bMono-, di- and tricarboxylic acid examples
Fig. 12.2.3b — Mono-, di- and tricarboxylic acid examples

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

Worked out. Propionic acid (CH3-CH2-COOH, one -COOH, a monocarboxylic acid); oxalic acid (HOOC-COOH, two -COOH groups directly bonded to each other, a dicarboxylic acid); and citric acid (HO-C(COOH)(CH2-COOH)2, a central carbon bearing an -OH plus three -COOH-bearing arms, a tricarboxylic acid) -- illustrating that carboxylic acids are further classified by how many -COOH groups the mole …

Figure 12.2.3cAromatic vs side-chain aromatic acids
Fig. 12.2.3c — Aromatic vs side-chain aromatic acids

Drawn by us to help you understand the concept clearly, and verified to make sure it's accurate. For exams, practice from your textbook's own diagram.

Worked out. Benzoic acid (a -COOH attached directly to the benzene ring) and phthalic acid (two -COOH groups directly attached to adjacent, ortho ring positions) as true aromatic carboxylic acids; aspirin/acetyl salicylic acid (a ring-COOH plus a ring-OCOCH3 ester substituent) as a further aromatic-acid example; contrasted with phenylacetic acid (C6H5-CH2-COOH), whose -COOH sits on a side-chain CH2 rather than directly on the ring, so the 'Remember' box classes it as a side-chain aromatic acid, …