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Carboxylic Acid: "COOH" Redirects Here. For The Bulgarian Musician, See
Carboxylic Acid: "COOH" Redirects Here. For The Bulgarian Musician, See
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). For trivial names, the suffix is usually ic acid (e.g., stearic acid).
Straight-chain, saturated carboxylic acids
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 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 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
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
Other carboxylic acids
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 andpyruvic acid
Aromaticcarboxylic
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 andaldaric 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
Carboxyl radical[edit]
The radical COOH (CAS# 2564-86-5) has only a separate fleeting existence.
[3]
The acid dissociation
constant of COOH has been measured using electron paramagnetic resonance spectroscopy.
[4]
The
carboxyl group tends to dimerise to form oxalic acid.
Physical properties[edit]
Solubility[edit]
Carboxylic acid dimers
Carboxylic acids are polar. Because they are both hydrogen-bond acceptors (the carbonyl -C=O)
and hydrogen-bond donors (the hydroxyl -OH), they also participate in hydrogen bonding. Together
the hydroxyl and carbonyl group forms the functional group carboxyl. Carboxylic acids usually exist
as dimeric pairs in nonpolar media due to their tendency to self-associate. Smaller carboxylic acids
(1 to 5 carbons) are soluble in water, whereas higher carboxylic acids are less soluble due to the
increasing hydrophobic nature of the alkyl chain. These longer chain acids tend to be rather soluble
in less-polar solvents such as ethers and alcohols.
[5]
Boiling points[edit]
Carboxylic acids tend to have higher boiling points than water, not only because of their increased
surface area, but because of their tendency to form stabilised dimers. Carboxylic acids tend to
evaporate or boil as these dimers. For boiling to occur, either the dimer bonds must be broken or the
entire dimer arrangement must be vaporised, both of which increase the enthalpy of
vaporization requirements significantly.
Acidity[edit]
Carboxylic acids are Brnsted-Lowry acids because they are proton (H
+
) donors. They are the most
common type of organic acid.
Carboxylic acids are typically weak acids, meaning that they only partially dissociate into
H
+
cations and RCOO
Na
+
+ CO2 + H2O
Carboxylic acids also react with alcohols to give esters. This process is heavily used
in the production of polyesters. Likewise, carboxylic acids are converted
into amides, but this conversion typically does not occur by direct reaction of the
carboxylic acid and the amine. Instead esters are typical precursors to amides. The
conversion of amino acids into peptides is a major biochemical process that
requires ATP.
The hydroxyl group on carboxylic acids may be replaced with a chlorine atom
using thionyl chloride to give acyl chlorides. In nature, carboxylic acids are
converted to thioesters.
Carboxylic acid can be reduced to the alcohol by hydrogenation or using
stoichiometric hydride reducing agents such as lithium aluminium hydride.
N,N-dimethylchloromethylenammonium chloride is a highly chemoselective agent
for carboxylic acid reduction. It selectively activate the carboxylic acid and is known
to tolerate active functionalities such as ketone as well as the moderate ester, olefin,
nitrile, and halide moeties.
[8]
Specialized reactions[edit]
As with all carbonyl compounds, the protons on the -carbon are labile due to
keto-enol tautomerization. Thus, the -carbon is easily halogenated in the Hell-
Volhard-Zelinsky halogenation.
The Schmidt reaction converts carboxylic acids to amines.
Carboxylic acids are decarboxylated in the Hunsdiecker reaction.
The Dakin-West reaction converts an amino acid to the corresponding amino
ketone.
In the Barbier-Wieland degradation, the alpha-methylene bridge in an aliphatic
carboxylic acid is removed in a sequence of reaction steps, in effect a chain-
shortening.
[9][10]
The inverse procedure is the Arndt-Eistert synthesis, where an
acid is converted into acyl halide and reacts with diazomethane to give the
highest homolog.
Many acids undergo oxidative decarboxylation. Enzymes that catalyze these
reactions are known ascarboxylases (EC 6.4.1) and decarboxylases (EC 4.1.1).
Carboxylic acids are reduced to aldehydes via the ester and DIBAL, via the acid
chloride in the Rosenmund reduction and via the thioester in the Fukuyama
reduction.
In ketonic decarboxylation carboxylic acids are converted to ketones.
The Kolbe electrolysis is an electrolytic, decarboxylative dimerization reaction.
In other words, it gets rid of the carboxyl groups of two acid molecules, and
joins the remaining fragments together.