School of CBMES Organic Chemistry 2 Laboratory

Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives

The characteristic functional group in a carboxylic acid is O

the carboxy group.
C CH2 O
HO CH2 C
O
OH
C Succinic acid
R OH
CH3
Carboxylic acids and their derivatives rank with
aldehydes and ketones among the most important organic CH2 C CH2

compounds because they occur widely in nature, and O C CH3 C OH

because they serve important roles in organic synthesis.
OH O
,-Dimethylglutaric acid
I. Common Nomenclature
Note: The mnemonic device to remember the names of
Common nomenclature is widely used for the dicarboxylic acids is the phrase, “Oh, My, Such Good Apple
simpler carboxylic acid. A carboxylic acid is named by Pie” which stands for oxalic, malonic succinic, glutaric,
adding the suffix ic and the word acid to the prefix adipic and pimelic acids.
for the appropriate functional groups.
Phthalic acid is an important aromatic dicarboxylic acid.
O
O
C
H3C OH C
Acet + ic acid = Acetic acid OH

OH
O C

C O
OH Phthalic acid

Many carboxylic acids are known even before the

Benzo + ic acid = Benzoic acid system of nomenclature existed. These include:

As with aldehydes and ketones, substitution in the O O

common system is denoted by Greek letters rather HO C C OH
than numbers. The position adjacent to the carboxy
CH HC
group is denoted by .
HO OH
O Tartaric acid

CH2 C O
H3C 2 CH OH
3 1 CH C
Br CH OH
-Bromobutyric acid

where: 1 is the  position Cinnamic acid

2 is the  position
3 is the  position O

C
Carboxylic acids containing two carboxy groups OH
are called dicarboxy acids. The unbranched
dicarboxylic acids are particularly important, and are OH
invariably known by their common names. Some of the Salicyclic acid
important dicarboxylic acids include:

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School of CBMES Organic Chemistry 2 Laboratory
Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives

II. Substitutive Nomenclature CH3 O

CH C
3 CH2 1
A carboxylic acid is named systematically by H2C
4 2
OH

dropping the final e from the name of the hydrocarbon CH3

5
with the same number of carbon atoms and adding the
3-Methylpentanoic acid
suffix oic and the word acid.
In carboxylic acids derived from cyclic
O
hydrocarbon, numbering begins at the ring carbon
C bearing the carboxy group.
H2C OH
O
CH3
2 C
Propan + oic acid = Propanoic acid 3 1 OH

4
The final e is not dropped in the name of the H3C
dicarboxylic acids. 4-Methylcyclohexanecarboxylic acid

O O O

C CH2 CH2 CH2 C C

HO CH2 CH2 CH2 CH2 OH OH

Nonanedioc acid
Br

When a carboxylic is derived from a cyclic 4-Bromobenzoic acid

hydrocarbon, the suffix carboxylic and the word acid or p-Bromobenzoic acid
are added to the name of the hydrocarbon.
When carboxylic acids contain other functional
O groups, the carboxy group receives priority over
aldehydes and ketone carbonyl group, over hydroxy
C
OH group and over mercapto groups for citation as the
principal group.

O H O
Cyclohexanecarboxylic acid
C C CH2 C
O OH H 7
C 5
CH 3
CH2 1 OH
O C 6 4 2
H OH
C
HO (E)-4-Hydroxy-7-oxo-5-heptenoic acid

O O
C
C OH
OH H2C
1,2,4-Benzenetricarboxylic acid
CH CH2 O
3 4
Note: One exception to this nomenclature is the H2C
2
CH2 C
5 6
benzoic acid, for which the IUPAC recognizes the C OH OH
1
common name. O
3-(Carboxymethyl)hexanedioc acid
The principal chain in substituted carboxylic acids
is numbered, as in aldehydes, by assigning number one
to the carbonyl group.

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Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives

Carboxylic acid derivatives are compounds that can be Br O

hydrolyzed under acidic or basic conditions to give a C

related carboxylic acid.
O

CH3

NOMENCLATURE AND CLASSIFICATION OF

Methyl 2-bromocyclohexanecarboxylate
CARBOXYLIC ACID DERIVATIVES
O
A. ESTERS AND LACTONES O CH2 C
C CH2 O
Esters are named as derivatives of their parent O CH
carboxylic acid by applying a variation of the system H2C H3C CH3

used in naming carboxylate salts. The group attached CH

H3C CH3
to the carboxylate oxygen is named first as a simple
alkyl or aryl group. This name is followed by the name Diisopropyl succinate
of the parent carboxylate which is constructed by
O
dropping the final ic from the name of the acid and
a
adding the suffix ate. This procedure is used in both
common and substitutive nomenclature. O b

CH3
O
-Butyrolactone
C C2H5 (a -lactone)
H3C O
Ethyl acetate (Common) where: a is the -position
b is the -position
O
O C O
CH2 CH2
CH2 CH2 a
O
CH2 CH3
b
Phenyl hexanoate ( Substitutive) c

-Butyrolactone
Substitution is indicated by numbering the acid (a -lactone)
portion of the ester as in carboxylic acid
nomenclature, beginning with the carbonyl as carbon-1 where: a is the -position
(substitutive nomenclature) or with the adjacent b is the -position
carbon as the -position (common nomenclature). The c is the -position
alkyl or aryl group is numbered from the point of
attachment to the carboxylate oxygen. In the common nomenclature, the name of a
lactone is derived from the acid with the same number
O of carbons in its principal chain; the ring size is
C CH2 CH3
denoted by a Greek letter corresponding to the point
H2C 1 O 1 CH 3 of attachment of the lactone ring oxygen to the
2 2
carbon chain.
CH Br
H3C 3 Cl
4 The substitutive nomenclature of lactones is a
Common name: -Bromopropyl -chlorobutyrate specialized extension of heterocyclic nomenclature.
Substitutive name: 2-Bromopropyl 3- chlorobutanoate
B. ACID HALIDES
Esters of other acids are named by analogous
extensions of acid nomenclature. Acid halides are named in any system of
nomenclature by replacing the ic ending of the acid
with the suffix yl, followed by the name of the halide.

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Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives

O (a mixed anhydride)
CH2 C
H3C Cl O

Propionyl chloride
O
Br O
Cl
H3C C C
O
C2H5 Br 4-Chlorophthalic anhydride
-Bromo--methylbutyryl bromide (a cyclic anhydride)
2-Bromo-2-methylbutanoyl bromide
D. NITRILES
O O
Nitriles are named in the common system by
C C
Cl CH2 Cl dropping the ic or oic from the name of the acid with
Malonyl dichloride the same number of carbon atoms (counting the nitrile
carbon) and adding the suffix onitrile.
O

C
In substitutive nomenclature, the suffix nitrile is
Cl added to the name of the hydrocarbon with the same
number of carbon atoms.

Cyclohexanecarbonyl chloride
C N
Notice in the last example the special
nomenclature required when the acid halide group is Benzonitrile (benz + onitrile)
attached to a ring; the compound is named as an
alkanecarbonyl halide. H3C C N
Acetonitrile (acet + onitrile)
C. ANHYDRIDES
CH3
To name an anhydride, the name of the parent acid N
CH C
is followed by the word anhydride. H3C CH2
Isovaleronitrile (common)
O O
3-Methylbutanenitrile (substitutive)
C C
Ph O Ph N
Benzoic anhydride CH2 C
C CH2
O O N
Succinonitrile (common)
C C Butanedinitrile (substitutive)
H 9 C4 O C4H9
valeric anhydride (common) The name of the three-carbon-nitrile is shortened
Pentanoic anhydride (substitutive) in common nomenclature:

Mixed anhydrides are named by citing the two CH2

parent acids in alphabetical order. H3C C
N
Propionitrile (not propiononitrile)
O O
When the nitrile group is attached to a ring, a
C C special carbonitrile nomenclature is used.
H3C O H
Acetic formic anhydride

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School of CBMES Organic Chemistry 2 Laboratory
Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives

N
O C2H5
C
C N
H3C
H3C C2H5
N,N-Diethylacetamide
2-Methylcyclobutanecarbonitrile
Cl

E. AMIDES, LACTAMS, AND IMIDES

O
C
Simple amides are named in any system by
replacing the ic or oic suffix of the acid name with the HN
CH3
suffix amide. N-Methyl-4-chlorocyclohexane carboxamide
O
Cyclic amides are called lactams, and the common
C
NH2 nomenclature of the simple lactams is analogous to
that of lactones. Lactams like lactones, are classified
by ring size as -lactams (5-membered lactam ring), -
Benzamide (benz + amide) lactams (4-membered lactam ring), and so on.

O O

H3C CH2 C
CH CH2 NH2
NH
Cl
-Chlorovaleramide (common) -Butyrolactam
4-Chloropentanamide (substitutive)
Imides are formally the nitrogen analogs of
When the amide functional group is attached to a anhydrides. Cyclic imides, of which the two compounds
ring; the suffix carboxamide is used. below are examples, are of greater importance than
open-chain imides, although the latter are also known
O
H3C compounds.
C
NH2 O
O

NH
2-Methylcyclopentanecarboxamide NH

O
Amides are classified as primary, secondary or O
tertiary according to the number of hydrogens on the Succinimide Phthalimide
amide nitrogen.

O H O H O R'' F. NOMENCLATURE OF SUBSTITUENT GROUPS

C N C N C N
The priorities for citing principal groups in a
R H R R' R R'
carboxylic acid derivative are as follows:
Primary amide Secondary amide Tertiary amide

Acid > Anhydride > Ester > Acid halide > amide > nitrile
Notice that this classification, unlike that of alkyl
halides and alcohols, refers to substitution at nitrogen
Examples:
rather than substitution at carbon. O

H3C C O
Substitution on nitrogen in secondary and tertiary
amides is designated with the letter N (italicized or NH C
underlined). OH

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Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives

p-Acetamidobenzoic acid
4-(Acetylamino)benzoic acid 1. 2-Methyl-4-ethyloctanoic acid

O 2. m-Nitrobenzoic acid

C OH 3. -Phenylbutyric acid
O 1 O 4. (Z)-3-Hexenoic acid
C 5 2 C
5. 1,4-Cyclohexanedicarboxylic acid
Cl 4 3 O
6. ,-Dichloropropionic acid
C H3C
7. 4-Methylhexanoic acid
N
5-Chloroformyl-4-cyano-2-methoxycarbonylbenzoic acid 8. p-Methoxybenzoic acid

9. 3-Hexenoic acid

G. CARBONIC ACID DERIVATIVES 10. 2-Methyl-4-hexenoic acid

11. 5-Cyanopentanoic acid

Esters of carbonic acid are named like any other
ester, but other important carbonic acid derivatives 12. Isopentyl acetate
have special names that should be named. 13. Ethyl p-nitrobenzoate

14. N,N- Dimethylbenzamide

Examples:
O 15. Diethyl succinate

C 16. 2-Bromopropanoyl bromide

H3CO OCH3
17. Diethyl phthalate
Dimethyl carbonate
O 18. Acrylonitrile

C 19. N,N – Dimethylformamide

Cl Cl
Phosgene 20. 3-Ethoxycarbonylhexanedionic acid

O II. Name the following compounds systematically.

C
H2N NH2 1.
Urea CH3

H3C C COOH
O
CH3
C
H2N OH
2. HO2C(CH2)7CH(CH3)2
Carbamic acid
(unstable, but has many stable derivatives) 3.
Cl
O COOH

C
H2N OCH3
methyl carbamate Cl

4.
HO COOH

Exercise No. 3: Nomenclature of Carboxylic acids and

Carboxylic acid Derivatives O

I. Give the structure of the following compounds:

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Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives

5. 16.
HOOC CH COOH O O

C C
CH3 H5C2O O CH2
6.
CH3
COOH
17.
H3C
7. O CH CH2
O
C O CH CH2
Cl C
OH H5C2O
18.
O

8.
O
O
19.
C O
OH
C CH2
H3CO O Cl
HS
20.
9.
O
CH3 O O

CH2HC

HOOC CH HC CH3
Br

CH3 CH3

10.
Br CH3

CH HC

HOOC CH HC CH3

CH3 OH

11.
Cl O
C

12.
H3C CH2

CH2 C N
13.
O
O O

14.
O CH3

C N

Ph CH3
15.
O O

C C
H5C2O CH2 CH2

CH3

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