A carboxylic acid /?k??rb?k's?l?

k/ is an organic compound that contains a carbox

yl group (C(=O)OH).[1] The general formula of a carboxylic acid is R COOH, with R
referring to the rest of the (possibly quite large) molecule. Carboxylic acids o
ccur widely and include the amino acids (which make up proteins) and acetic acid
(which is part of vinegar and occurs in metabolism).
Salts and esters of carboxylic acids are called carboxylates. When a carboxyl gr
oup is deprotonated, its conjugate base forms a carboxylate anion. Carboxylate i
ons are resonance-stabilized, and this increased stability makes carboxylic acid
s more acidic than alcohols. Carboxylic acids can be seen as reduced or alkylate
d forms of the Lewis acid carbon dioxide; under some circumstances they can be d
ecarboxylated to yield carbon dioxide.
Contents [hide]
1 Example carboxylic acids and nomenclature
2 Carboxyl radical
3 Physical properties
3.1 Solubility
3.2 Boiling points
3.3 Acidity
3.4 Odor
4 Characterization
5 Occurrence and applications
6 Synthesis
6.1 Industrial routes
6.2 Laboratory methods
6.3 Less-common reactions
7 Reactions
7.1 Specialized reactions
8 See also
9 References
10 External links
Example carboxylic acids and nomenclature[edit]
Carboxylic acids are commonly identified using their trivial names, and usually
have the suffix -ic acid. IUPAC-recommended names also exist; in this system, ca
rboxylic acids have an -oic acid suffix.[2] For example, butyric acid (C3H7CO2H)
is butanoic acid by IUPAC guidelines. The -oic acid nomenclature detail is base
d on the name of the previously-known chemical benzoic acid.[citation needed] Fo
r nomenclature of complex molecules containining a carboxylic acid, the carboxyl
can be considered position one of the parent chain even if there are other subs
tituents, for example, 3-chloropropanoic acid. Alternately, it can be named as a
"carboxy" or "carboxylic acid" substituent on another parent structure, for exa
mple, 2-carboxyfuran.
The carboxylate anion (R COO-) of a carboxylic acid is usually named with the suff
ix -ate, in keeping with the general pattern of -ic acid and -ate for a conjugat
e acid and its conjugate base, respectively. For example, the conjugate base of
acetic acid is acetate.
Straight-chain, saturated carboxylic acids
Carbon
atoms Common name IUPAC name Chemical formula Common location
or use
1 Carbonic acid Carbonic acid OHCOOH Blood and tissues (bicarbonate b
uffer system)
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, body odour
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 was
h soaps
13 Tridecylic acid Tridecanoic acid CH3(CH2)11COOH
14 Myristic acid Tetradecanoic acid CH3(CH2)12COOH Nutmeg
15 Pentadecylic acid 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
19 Nonadecylic acid Nonadecanoic acid CH3(CH2)17COOH Fats, ve
getable oils, pheromone
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=CHCO
OH, used in polymer synthesis
Fatty acids medium to long-chain saturated and unsaturated monocarboxylic ac
ids, with even number of carbons examples docosahexaenoic acid and eicosapentaen
oic 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 s
kin-care products, phenyl alkanoic acids the class of compounds where a phenyl g
roup is attached to a carboxylic acid.
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 fou
nd in citrus fruits and isocitric acid
Alpha hydroxy acids containing a hydroxy group example glyceric acid, glycol
ic acid and lactic acid (2-hydroxypropanoic acid) found in sour milk tartaric ac
id found in wine
Divinylether fatty acids containing a doubly unsaturated carbon chain att
ached via an ether bond to a fatty acid, found in some plants
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 a
cid.