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
138 ºC
slightly soluble
CH3(CH2)3CHO
pentanal
86
103 ºC
CH3CO2C2H5
ethyl ethanoate
77 ºC
moderately soluble
CH3CH2CO2CH3
methyl propanoate
80 ºC
CH3(CH2)2CONH2
butanamide
87
216 ºC
soluble
CH3CON(CH3)2
N,N-dimethylethanamide
165 ºC
CH3(CH2)4NH2
1-aminobutane
CH3(CH2)3CN
pentanenitrile
83
140 ºC
CH3(CH2)4CH3
hexane
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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