Nomenclature and Examples
Carboxylic acids are commonly named as indicated in the table below. Although rarely used, IUPAC-recommended names also exist. For example, butyric acid (C3H7CO2H) is, according to IUPAC guidelines, also known as butanoic acid.
The carboxylate anion R-COO– is usually named with the suffix -ate, so acetic acid, for example, becomes acetate ion. In IUPAC nomenclature, carboxylic acids have an -oic acid suffix (e.g., octadecanoic acid). In common nomenclature, the suffix is usually -ic acid (e.g., stearic acid).
Carbon atoms | Common name | IUPAC name | Chemical formula | Common location or use |
---|---|---|---|---|
1 | Formic acid | Methanoic acid | HCOOH | Insect stings |
2 | Acetic acid | Ethanoic acid | CH3COOH | Vinegar |
3 | Propionic acid | Propanoic acid | CH3CH2COOH | Preservative for stored grains |
4 | Butyric acid | Butanoic acid | CH3(CH2)2COOH | Rancid butter |
5 | Valeric acid | Pentanoic acid | CH3(CH2)3COOH | Valerian |
6 | Caproic acid | Hexanoic acid | CH3(CH2)4COOH | Goat fat |
7 | Enanthic acid | Heptanoic acid | CH3(CH2)5COOH | |
8 | Caprylic acid | Octanoic acid | CH3(CH2)6COOH | Coconuts and breast milk |
9 | Pelargonic acid | Nonanoic acid | CH3(CH2)7COOH | Pelargonium |
10 | Capric acid | Decanoic acid | CH3(CH2)8COOH | |
11 | Undecylic acid | Undecanoic acid | CH3(CH2)9COOH | |
12 | Lauric acid | Dodecanoic acid | CH3(CH2)10COOH | Coconut oil and hand wash soaps. |
13 | Tridecylic acid | Tridecanoic acid | CH3(CH2)11COOH | |
14 | Myristic acid | Tetradecanoic acid | CH3(CH2)12COOH | Nutmeg |
15 | Pentadecanoic acid | CH3(CH2)13COOH | ||
16 | Palmitic acid | Hexadecanoic acid | CH3(CH2)14COOH | Palm oil |
17 | Margaric acid | Heptadecanoic acid | CH3(CH2)15COOH | |
18 | Stearic acid | Octadecanoic acid | CH3(CH2)16COOH | Chocolate, waxes, soaps, and oils |
20 | Arachidic acid | Icosanoic acid | CH3(CH2)18COOH | Peanut oil |
Compound class | Members |
---|---|
unsaturated monocarboxylic acids | acrylic acid (2-propenoic acid) – CH2=CHCOOH, used in polymer synthesis |
Fatty acids | medium to long-chain saturated and unsaturated monocarboxylic acids, with even number of carbons examples docosahexaenoic acid and eicosapentaenoic acid (nutritional supplements) |
Amino acids | the building blocks of proteins |
Keto acids | acids of biochemical significance that contain a ketone group e.g. acetoacetic acid and pyruvic acid |
Aromatic carboxylic acids | benzoic acid, the sodium salt of benzoic acid is used as a food preservative, salicylic acid – a beta hydroxy type found in many skin care products |
Dicarboxylic acids | containing two carboxyl groups examples adipic acid the monomer used to produce nylon and aldaric acid – a family of sugar acids |
Tricarboxylic acids | containing three carboxyl groups example citric acid – found in citrus fruits and isocitric acid |
Alpha hydroxy acids | containing a hydroxy group example glyceric acid, glycolic acid and lactic acid (2-hydroxypropanoic acid) – found in sour milk tartaric acid – found in wine |
Read more about this topic: Carboxylic Acid
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