Depto. Química Orgánica

PHYSICAL PROPERTIES OF CARBOXYLIC ACIDS

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15/07/2017
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Physical properties of carboxylic acids
The alifatic monocarboxylic acids are well known from a long time ago because they can be obtained from a number of common natural sources.
They have in many cases trivial names.
Formula
R-CO2H
IUPAC
Name
(... acid)
Trivial
name
(...acid)
M.P. B.P.
(mm Hg)
Solubility
in water
(g/L)
Natural
source
HMetanoic
Formic8101(763)unlimitedAnts
CH3Etanoic
Acetic17118(763)unlimitedVinegar (wine)
CH3CH2Propanoic
Propionic-21141(763)unlimitedDairy
Products
CH3(CH2)2Butanoic
Butyric-5164(763)unlimitedRancid butter
cheese
CH3(CH2)3Pentanoic

Pentanoic
Valeric-34186(763)50Valerian root
CH3(CH2)4Hexanoic
Caproic-3205(763)10Goats
CH3(CH2)5Heptanoic

Heptanoic
Enantic-8223(763)2Wine
CH3(CH2)6Octanoic
Caprylic17239(763)0.7Goat butter
CH3(CH2)7Nonanoic
Pelargonic15255(763)0.3Geranium
leaves
CH3(CH2)8Decanoic
Capric32270(763)0.2Cocoa butter
CH3(CH2)10Dodecanoic
Lauric44299(763)0.01Laurel leaves
CH3(CH2)12Tetradecanoic
Mirystic54251(100)<0.01Nutmeg
CH3(CH2)14Hexadecanoic
Palmytic63267(100)<0.01Palm oil
CH3(CH2)16Octadecanoic

Estearic72183(1)<0.01Cocoa butter
Alifatic dicarboxylic acids are also well known.
They are important synthetic intermediates.
Formula
HO2C-X-CO2H
IUPAC
Name
(...acid)
Trivial
name
(...acid)
M.P.Natural
source
---Etanodioic

Oxalic190kidney
stones
CH2Propanodioic

Malonic136apples
(CH2)2Butanodioic

Succinic188Amber
(CH2)3Pentanodioic

Glutaric96beet
wood
(CH2)4Hexanodioic

Adipic153NON natural
nylon
CH=CH (cis)cis-butenodioic

Maleic141NON natural
CH=CH (trans)trans-butenodioic

Fumaric299metabolic
intermediate
C(triple)CButynodioic

Acetylen-
dicarboxilic
185NON natural