aldehydes and ketones among the most important organic compounds because their occur widely in nature, and because they serve important roles in organic synthesis.
Carboxylic Acid
y ALIPHATIC ACID
carboxyl group y AROMATIC ACID has an aryl group; the simplest acid is formic acid, with a proton bonded to the carboxyl group y FATTY ACIDS are long-chain aliphatic acids derived from the hydrolysis of fats and oils
BOILING POINTS
y Carboxylic acid boils at considerably higher
temperature than do alcohols, ketones or aldehydes of similar molecular weights. y High boiling points of carboxylic acids result from formation of a stable hydrogen-bonded dimmer. y This dimmer contains an eight-membered ring joined by two hydrogen bonds, effectively doubling
MELTING POINTS
y Avoid containing more than 8 carbon atoms are
generally solids, unless they contain double bonds. y The presence of double bonds (especially as double bonds) in a long chain impedes the formation of a stable crystal lattice, resulting in a lower melting point. y Dicarboxylic acid melting point is relatively high
formicus, for ant y It was first isolated by the distillation of red ants. y It is partially responsible for the irritation of ant bites and bee stings.
ferment, which changes the sugar present to ethanol. y Pure acetic acid has a penetrating odor and produces painful burns
OXALIC ACID
y Is a dicarboxylic acid with the formula (CO2H2) or
H2C2O4. y Its molecule consists of two carboxyl groups ( dicarboxylic) bonded together.
Common Nomenclature
y The characteristic functional group in a carboxylic acid is the carboxy group.
O R C OH
Common Nomenclature
y Common names for aliphatic carboxylic acids are often
derived from the name of a natural substance from which the acid can be isolated.
O
OH
H3C
OH
Greek letters rather than numbers. y The position adjacent to the carboxy group is denoted by E.
O H3C
3
CH2 CH
2 1
OH
E-bromobutyric acid
Br
HOOC
CH2 CH2
Succinic acid
COOH
HOOC
CH 2 C CH 3
CH 2 COOH
F,F-dimethylglutaric acid
dicarboxylic acids is the phrase, Oh, My, Such Good Apple Pie which stands for oxalic, malonic, succinic, glutaric, adipic and pimelic acids.
acid.
COOH
Phthalic acid
COOH
Ph
CH
CH
COOH
Cinnamic acid
COOH
Tartaric acid
Salicyclic acid
OH
dropping the final e from the name of the hydrocarbon with the same number of carbon atoms and adding the suffix oic and the word acid.
O H3C CH2 C OH
Propan + oic acid = propanoic acid
dicarboxylic acids.
HOOC CH2 CH2 CH2 CH2 CH2 CH2 CH2 COOH
Nonanedioic acid
hydrocarbon, the suffix carboxylic and the word acid are added to the name of the hydrocarbon.
COOH
COOH
HOOC
Cyclohexanecarboxylic acid
COOH
1,2,4-benzenetricarboxylic acid
CH2
2
COOH
1
3-methylpentanoic acid
COOH
COOH
H3C
4-methylcyclohexanecarboxylic acid
Br
4-hydroxy-7-oxo-5-heptenoic acid
CH2 HC
2 3
3-(carboxymethyl)hexane-1,6-dioic acid
Fatty Acids
y Long, unbranched carboxylic acids, most commonly
consisting of 12 to 20 carbons. y Derived from the hydrolysis of animal fats, vegetable oils, or the phospholipids of biological membrane. y Can saturated or unsaturated fatty acids. y Used in the preparation of detergents and soap. (saponification)
bonded to an OR group. yEsters are named as derivatives of their parent carboxylic acid by applying a variation of the system used in naming carboxylate salts. yThe group attached to the carboxylate oxygen is named first as a simple alkyl or aryl group. yThis name is followed by the name of the parent carboxylate which is constructed by dropping the final ic from the name of the acid and adding the suffix ate.
H3C
C2H5
portion of the ester as in carboxylic acid nomenclature, beginning with the carbonyl as carbon-1 (substitutive nomenclature) or with the adjacent carbon as the E-position (common nomenclature). yThe alkyl or aryl group is numbered from the point of attachment to the carboxylate oxygen.
O H3C CH CH2
4 3 2
C
1
CH2 CH CH3
1 2 3
Cl
Br
two carbonyl groups bonded to the same oxygen atom. yTo name an anhydride, the name of the parent acid O is followed byO word anhydride. the
Ph
Ph
Benzoic anhydride
O H 3C C O
O C H
atoms bonded to a carbon atom is replaced by a nitrogen atom. yNitriles are named in the common system by dropping the ic or oic from the name of the acid with the same number of carbon atoms (counting the nitrile carbon) and adding the suffix onitrile. yIn substitutive nomenclature, the suffix nitrile is added to the name of the hydrocarbon with the same number of carbon atoms.
N
N
Benzonitrile ( benz + onitrile ) Acetonitrile ( acet + onitrile ) Isovaleronitrile (common) N 3-methylbutanenitrile (substitutive) succinonitrile (common) butanedinitrile (substitutive)
C CH2 CH2 C
in common nomenclature:
CH3CH2 CN propionitrile (not propiononitrile)
When the nitrile group is attached to a ring, a special carbonitrile nomenclature is used.
CH3
2-methylcyclobutanecarbonitrile
group bonded to a nitrogen atom ySimple amides are named in any system by replacing the ic or oic suffix of the acid name with the suffix amide. O
C NH2
NH2
2-methylcyclopentanecarboxamide
O R N
H
R
O N
H
R
O N
R''
H
Primary amide
R'
R'
halides and alcohols, refers to substitution at nitrogen rather than substitution at carbon. ySubstitution on nitrogen in secondary and tertiary amides is designated with the letter N (italicized or underlined).
C 2H 5
C 2H 5
N,N-diethylacetamide
O C HN CH3
N-methyl-4-chlorocyclohexane carboxamide