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  Nomenclature of Carboxylic Acids Homework Help - K-12 Grade Level, College Level Chemistry

Introduction to Carboxylic Acids

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The carboxyl functional group that characterizes the carboxylic acids is not usual in that it is composed of two functional groups explained previous. As might be seen in the formula on the right side, carboxyl group is made up of a hydroxyl group bonded to a carbonyl group. It is frequently written in condensed form like -CO2H or -COOH. Another combination of functional groups was explained previously, and important changes in chemical behavior as a result of group interactions were explained (for example phenol & aniline). In this example, the change in physical and chemical properties resultant from the interaction of the carbonyl and hydroxyl group are so profound that the combination is customarily treated as a different and distinct functional group.

Nomenclature of Carboxylic Acids

The carboxyl group must be situated at the end of a carbon chain, such as with aldehydes. The carboxyl carbon is entitled no.1, in the IUPAC system of nomenclature, and other substituents are located and named consequently. The feature IUPAC suffix for a carboxyl group is "oic acid", and care must be taken not to confuse this systematic nomenclature with identical common system. These two nomenclatures are depicted in the table, along with their boiling and melting points.

Formula

Common Name

Source

IUPAC Name

Melting Point

Boiling Point

HCO2H

formic acid

ants (L. formica)

methanoic acid

8.4 ºC

101 ºC

CH3CO2H

acetic acid

vinegar (L. acetum)

ethanoic acid

16.6 ºC

118 ºC

CH3CH2CO2H

propionic acid

milk (Gk. protus prion)

propanoic acid

-20.8 ºC

141 ºC

CH3(CH2)2CO2H

butyric acid

butter (L. butyrum)

butanoic acid

-5.5 ºC

164 ºC

CH3(CH2)3CO2H

valeric acid

valerian root

pentanoic acid

-34.5 ºC

186 ºC

CH3(CH2)4CO2H

caproic acid

goats (L. caper)

hexanoic acid

-4.0 ºC

205 ºC

CH3(CH2)5CO2H

enanthic acid

vines (Gk. oenanthe)

heptanoic acid

-7.5 ºC

223 ºC

CH3(CH2)6CO2H

caprylic acid

goats (L. caper)

octanoic acid

16.3 ºC

239 ºC

CH3(CH2)7CO2H

pelargonic acid

pelargonium (an herb)

nonanoic acid

12.0 ºC

253 ºC

CH3(CH2)8CO2H

capric acid

goats (L. caper)

decanoic acid

31.0 ºC

219 ºC

Substituted carboxylic acids are termed either by the IUPAC system or by common names. If you are not sure about the IUPAC rules for nomenclature you should reconsider them again. Some general names, the amino acid threonine for instance, do not have any systematic origin and must simply be memorized. In other instances, common names use the Greek letter notation for carbon atoms near the carboxyl group. Some instances of both nomenclatures are provided below.

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Simple dicarboxylic acids containing the general formula HO2C-(CH2)n-CO2H (where n = 0 to 5) are known by the common names: Oxalic (n=0), Malonic (n=1), Succinic (n=2), Glutaric (n=3), Adipic (n=4) and Pimelic (n=5) Acids. Common names, like these can be troublesome to remember, so mnemonic aids that take the form of a catchy phrase, have been devised. For this group of the compounds one such phrase is: "Oh My Such Good Apple Pie".

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