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  Physical of Properties Carboxylic Derivatives Homework Help - K-12 Grade Level, College Level Chemistry

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

87

205 -210 ºC

soluble

CH3CON(CH3)2

N,N-dimethylethanamide

87

166 ºC

very soluble

HCON(CH3)CH2CH3

N-ethyl, N-methylmethanamide

87

170-180 ºC

very soluble

CH3(CH2)3CN

pentanenitrile

83

141 ºC

slightly soluble

CH3CO2CHO

ethanoic methanoic 
anhydride

88

105-112 ºC

reacts with water

CH3CH2CO2CH3

methyl propanoate

88

80 ºC

slightly soluble

CH3CO2C2H5

ethyl ethanoate

88

77 ºC

moderately soluble

CH3CH2COCl

propanoyl chloride

92.5

80 ºC

reacts with water

CH3(CH2)3CHO

pentanal

86

103 ºC

slightly soluble

CH3(CH2)2COCH3

2-pentanone

86

102 ºC

slightly soluble

 

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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