Introduction to Physical Properties of Carboxylic Derivatives
The significant classes of organic compounds termed as ethers, amines, alcohols, phenols, and halides contain alkyl and/or aryl groups bonded to alkoxyl, amino, hydroxyl, and halo substituents correspondingly. Their properties are considerably changed, If these same functional groups are attached to an acyl group (RCO-) and they are entitled as carboxylic acid derivatives. The Carboxylic acids contain a hydroxyl group bonded to an acyl group and their functional derivatives are prepared by replacement of the hydroxyl group with substituents, like alkoxyl, amino, halo, and acyloxy. Some instances of these functional derivatives were shown previous. The table below lists some representative derivatives and their boiling points. An aldehyde and ketone of corresponding molecular weight are also listed for comparison. Boiling points are given for 760 torr (atmospheric pressure), and those listed as a range are approximate from values acquired at lower pressures. As noted earlier, the comparatively high boiling point of carboxylic acids is because of wide hydrogen bonded dimerization. Identical hydrogen bonding takes place between molecules of 1º and 2º-amides (amides having at least one N-H bond) and the top first three compounds in the table serve as hydrogen bonding examples.
Physical Properties of Some Carboxylic Acid Derivatives
Formula
IUPAC Name
Molecular Weight
Boiling Point
Water Solubility
CH3(CH2)2CO2H
butanoic acid
88
164 ºC
very soluble
CH3(CH2)2CONH2
butanamide
87
216-220 ºC
soluble
CH3CH2CONHCH3
N-methylpropanamide
205 -210 ºC
CH3CON(CH3)2
N,N-dimethylethanamide
166 ºC
HCON(CH3)CH2CH3
N-ethyl, N-methylmethanamide
170-180 ºC
CH3(CH2)3CN
pentanenitrile
83
141 ºC
slightly soluble
CH3CO2CHO
ethanoic methanoic anhydride
105-112 ºC
reacts with water
CH3CH2CO2CH3
methyl propanoate
80 ºC
CH3CO2C2H5
ethyl ethanoate
77 ºC
moderately soluble
CH3CH2COCl
propanoyl chloride
92.5
CH3(CH2)3CHO
pentanal
86
103 ºC
CH3(CH2)2COCH3
2-pentanone
102 ºC
The last nine entries in the table cannot function as hydrogen bond donors, so hydrogen bonded aggregates and dimers are not possible. The comparatively high boiling points of equivalent 3º-amides and nitriles are almost certainly because of the high polarity of these functions. Certainly, if hydrogen bonding is not exist, the boiling points of comparable sized compounds associate reasonably well with their dipole moments.
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