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Introduction to Physical Properties of Carboxylic Acids

The boiling points increased with size in a usual way, but the melting points did not. Unbranched acids made up of even number of carbon atoms have melting points higher than the odd numbered homologs having one more or one less carbon. This reflects variations in intermolecular attractive forces in the crystalline state. In the table of fatty acids we observe that the existence of a cis-double bond considerably lowers the melting point of a compound. So, palmitoleic acid melts over 60º lower than palmitic acid, and similar decreases take place for the C18 and C20 compounds. Again, changes in crystal intermolecular forces and packing are accountable.

The issues that affect the relative boiling points and water solubilities of several kinds of compounds were discussed previous. Generally, dipolar attractive forces among molecules act to increase the boiling point of a given compound, with hydrogen bonds being an extreme instance. Hydrogen bonding is also a chief issue in the water solubility of covalent compounds. The following table lists a few illustrations of these properties for some identical sized polar compounds (the non-polar hydrocarbon hexane is presented for comparison).

Physical Properties of Some Organic Compounds

Formula

IUPAC Name

Molecular Weight

Boiling Point

Water Solubility

CH3(CH2)2CO2H

butanoic acid

88

164 ºC

very soluble

CH3(CH2)4OH

1-pentanol

88

138 ºC

slightly soluble

CH3(CH2)3CHO

pentanal

86

103 ºC

slightly soluble

CH3CO2C2H5

ethyl ethanoate

88

77 ºC

moderately soluble

CH3CH2CO2CH3

methyl propanoate

88

80 ºC

slightly soluble

CH3(CH2)2CONH2

butanamide

87

216 ºC

soluble

CH3CON(CH3)2

N,N-dimethylethanamide

87

165 ºC

very soluble

CH3(CH2)4NH2

1-aminobutane

87

103 ºC

very soluble

CH3(CH2)3CN

pentanenitrile

83

140 ºC

slightly soluble

CH3(CH2)4CH3

hexane

86

69 ºC

insoluble

The first five entries all of them have oxygen functional groups, and the comparatively high boiling points of the first two are clearly because of hydrogen bonding. Carboxylic acids have very high boiling points, suitable in large part to dimeric associations involving two hydrogen bonds. A structural formula for dimer of acetic acid is displayed here. The high boiling points of the nitriles and amides are suitable in large part to strong dipole attractions, supplemented in some examples by hydrogen bonding.

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