Carboxylic acid

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"COOH" redirects here. For the Bulgarian musician, see Ivan Shopov.

Structure of a carboxylic acid

Carboxylate Anion

3D structure of a carboxylic acid

A carboxylic acid is an organic compound that contains a carboxyl group (C(=O)OH).[1] The
general formula of a carboxylic acid is R–COOH, with R referring to the alkyl group. Carboxylic acids
occur widely. Important examples include the amino acids and acetic acid. Deprotonation of a
carboxyl group gives a carboxylate anion.

Contents

 1Examples and nomenclature

 2Physical properties
 o 2.1Solubility

o 2.2Boiling points

o 2.3Acidity

o 2.4Odour

o 2.5Characterization

 3Occurrence and applications

 4Synthesis

o 4.1Industrial routes

o 4.2Laboratory methods

o 4.3Less-common reactions

 5Reactions

o 5.1Reduction

o 5.2Specialized reactions

 6Carboxyl radical

 7See also

 8References

 9External links

Examples and nomenclature[edit]

Carboxylic acids are commonly identified by their trivial names. They often have the suffix -ic
acid. IUPAC-recommended names also exist; in this system, carboxylic acids have an -oic
acid suffix.[2] For example, butyric acid (C3H7CO2H) is butanoic acid by IUPAC guidelines. For
nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered
position one of the parent chain even if there are other substituents, such as 3-chloropropanoic acid.
Alternately, it can be named as a "carboxy" or "carboxylic acid" substituent on another parent
structure, such as 2-carboxyfuran.
The carboxylate anion (R–COO− or RCO2−) of a carboxylic acid is usually named with the suffix -ate,
in keeping with the general pattern of -ic acid and -ate for a conjugate acid and its conjugate base,
respectively. For example, the conjugate base of acetic acid is acetate.

Straight-chain, saturated carboxylic acids

Carbo
Common Chemical
n IUPAC name Common location or use
name formula
atoms

Blood and tissues (bicarbonate buffer

1 Carbonic acid Carbonic acid OHCOOH
system)

1 Formic acid Methanoic acid HCOOH Insect stings

2 Acetic acid Ethanoic acid CH3COOH Vinegar

Preservative for stored grains, body

3 Propionic acid Propanoic acid CH3CH2COOH
odour, milk, butter, cheese

4 Butyric acid Butanoic acid CH3(CH2)2COOH 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 Enantic (vine blossom)

8 Caprylic acid Octanoic acid CH3(CH2)6COOH Coconuts

9 Pelargonic acid Nonanoic acid CH3(CH2)7COOH Pelargonium

10 Capric acid Decanoic acid CH3(CH2)8COOH Coconut and Palm kernel oil

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

Tetradecanoic
14 Myristic acid CH3(CH2)12COOH Nutmeg
acid

Pentadecylic Pentadecanoic
15 CH3(CH2)13COOH
acid acid

Hexadecanoic
16 Palmitic acid CH3(CH2)14COOH Palm oil
acid

Heptadecanoic
17 Margaric acid CH3(CH2)15COOH
acid

Octadecanoic
18 Stearic acid CH3(CH2)16COOH Chocolate, waxes, soaps, and oils
acid

Nonadecylic Nonadecanoic
19 CH3(CH2)17COOH Fats, vegetable oils, pheromone
acid acid

20 Arachidic acid Icosanoic acid CH3(CH2)18COOH Peanut oil

Other carboxylic
acids