NAMING OF

CARBOXYLIC ACID AND

ITS DERIVATIVES

Submitted by: Frances Anne A. Portugal

Submitted to: Professor Jericha Carina Victorino-Pascua

ORGANIC AND INORGANIC CHEMISTRY

MEDTECH-1-Y1-3
Carboxylic acid: an organic compound that contains a carboxyl group (-C (=O) OH). The
general formula of a carboxylic acid is R-COOH, with R referring to the rest of the molecule.
There should not be more than two (2) carboxyl groups on the root chain as they must occur at
the ends.

Nomenclature of Carboxylic Acid

1. Carboxylic acids are named by counting the number of carbons

in the longest continuous chain including the carboxyl group and by
replacing the suffix –ane of the corresponding alkane with –anoic acid.

2. If there are two –COOH groups, the suffix is expanded to

include a prefix that indicates the number of –COOH groups present (-
anedioic acid).

3. It is not necessary to indicate the position of the –COOH group

because this group will be at the end of the root chain and its carbon is
automatically assigned as number 1.

4. The carboxyl group takes precedence over all other groups in the
numbering of the root chain.

5. If the carboxyl group is attached to a ring, the parent ring is

named and the suffix –carboxylic acid is added.

6. When both double bonds and carboxyl groups are present, the –
en suffix follows the root chain directly and the –oic acid suffix follows
the –en suffix (the e is left off, -en instead of –ene).

7. The location of the double bonds are indicated before the root
name as before, and the –oic acid suffix follows the –en suffix directly.

8. If there is a choice in numbering not previously covered, the root

chain is numbered to give the substituents the lowest number at the first
point of difference.
Example #1: Carboxylic acid with aromatic ring Example #2: Carboxylic acid with
a saturated hydrocarbon

Pentanoic acid
Benzoic acid

Example #3: Carboxylic acid with unsaturated aliphatic hydrocarbon

2-Butenoic acid

Acyl halide: an organic compound derived from a carboxylic acid by replacing a hydroxyl group
with a halide (-Cl, -Br, -I, -F) group. The compound contains a –C (=O)-X functional group,
which consists of a carbonyl group singly bonded to a halogen atom. The general formula for
such an acyl halide can be written R-COX, where R may be an alkyl group, CO is the carbonyl
group, and X represents the halide. Acyl halides is also called acid halides.

Nomenclature of Acyl halides

1. The root name is based on the longest chain including the

carbonyl group of the acyl group.

2. The substituent suffix is –oyl halide.

 The –ic acid ending is removed and replaced with the ending -
ending is removed and replaced with the ending –yl followed by
the name of the halogen with an –ide ending. This is true for
both common and IUPAC nomenclature.


3. The carbonyl carbon is given the location number 1. It is not

necessary to include the location number in the name because it is
assumed that the functional group will be on the end of the root chain.
 4. As substituents they have the priority before amides and nitriles,
but after esters.

5. Acyl halide as substituent has the prefix halo carbonyl- (where

halo can be chloro, bromo, iodo, or fluoro)

6. If more than one functional group, this is indicated by using a

numbering prefix (-edi-) directly before the –oyl prefix and before the
halide.

Example #1: Acyl halides with aromatic ring Example #2: Acyl halides with a
saturated hydrocarbon

3-Methylbutanoyl
Benzoyl iodide bromide

Example #3: Acyl halides with unsaturated aliphatic hydrocarbon

2-Propenoyl chloride
Acid anhydride: The acid anhydride functional group results when two carboxylic acids
combine and lose water (anhydride = without water). Symmetrical acid anhydrides are named
like carboxylic acids except the ending –acid is replaced with –anhydride. This is true for both
the IUPAC and Common nomenclature.

Nomenclature of Acid anhydrides

Symmetrical anhydrides Unsymmetrical anhydrides

A symmetrical A mixed or
anhydride is a carboxylic unsymmetrical anhydride is a
acid anhydride that has the carboxylic acid anhydride
following general that has the following
structural formula. general structural formula.

Where R1=R2= Where R1 ≠ R2, but

hydrogen atoms, alkyl are hydrogen atoms, alkyl
groups, aryl groups groups, aryl groups. When
naming unsymmetrical acid
anhydrides, name both using
alkanoic general method and
then put the two names
alphabetically. Hence, first
name each component and
alphabetically arranged them
followed by spaces and then
the word anhydride.
 Example #1: Acid anhydrides Example #2: Acid anhydrides
with aromatic ring with a saturated hydrocarbon

Propanoic anhydride
Benzoic propanoic
anhydride

Example #3: Acid anhydrides with unsaturated aliphatic hydrocarbon

Butenoic ethanoic anhydride

Amides: Amides are amine derivatives of carboxylic acids, by replacing a hydroxyl group with
an amin group. The general formula R-C (=O) N (R’, R”), where C (=O) is the carbonyl group,
R may be a substituent as an alkyl group or hydrogen connected to the carbonyl, N is a nitrogen
atom connected to the carbonyl and R’ and R” represents substituents as alkyl groups or
hydrogen connected to the nitrogen. Amides are also called carboxamides or organic amides.

Nomenclature of Amides

1. Amides are named by counting the number of carbons in the

longest continuous chain including the carboxyl group and by
replacing the suffix –ane of the corresponding alkane with –
anamide.

2. When both double bonds and carboxyl groups are present, the –
en suffix follows the root chain directly and the –amide suffix
follows the –en suffix (the e is left off, -en instead of –ene)

3. Since the amide group is at the end of the chain, the C=O carbon
must be C1, and it is not necessary to include the location
number in the name.
 4. If the amide nitrogen has a substituent (secondary amide), the
substituent are given N- as the locant.

5. Tertiary amides (two substituents to the amide nitrogen) are

named in the same way as secondary amides, but with two N’s.

6. The N- locant is listed first.

Example #1: Amides with aromatic ring Example #2: Amides with a
saturated hydrocarbon

3-Chlorobenzamide N, N-Dimethylpropanamide

Example #3: Amides with unsaturated aliphatic hydrocarbon

N-Ethyl-2-butenamide
Esters: An ester is a compound containing an oxycarbonyl group, with the general formula R-C
(=O) O-R’. It can be derived from the carboxylic acid RCO2H and the alcohol R’OH.

Nomenclature of Esters

1. The first component of an ester name, the alkyl is derived from

the alcohol, R’-OH portion of the structure.

2. The second component of an ester name, the –oate is derived

from the carboxylic acid, R-CO2H portion of the structure.

3. Alcohol component
1. The root name is based on the longest chain containing the –OH
group.
2. The chain is numbered so as to give the –OH the lowest possible
number.

4. Carboxylic acid component

1. The root named is based on the longest chain including the carbonyl
group.
2. Since the carboxylic acid group is at the end of the chain, it must be
C1.
3. The ester suffix for the acid component is appended after the
hydrocarbon suffix minus the “e”: e.g. –ane + -oate = -anoate.

5. The complete ester name is the alkyl alkanoate

6. The oxycarbonyl group takes precedence after carboxylic acids,

but over acyl halides and amides, in the naming and numbering of the
root chain.
Example #1: Esters with aromatic ring Example #2: Esters with a
saturated hydrocarbon

ethyl hexanoate
methylbenzoate

Example #3: Esters with unsaturated aliphatic hydrocarbon

Ethyl 2-butenoate
Nitriles: Organic compound that contains an alkyl combined with a -C≡N functional group.
Nitriles are also called cyanides, but this is more common in inorganic chemistry. The nitrile
group can also be substituted to other types of hydrocarbons. If it is connected to e.g. an alkene,
it will be a nitroalkene.

Nomenclature of Nitriles

There are two different ways of

naming these compounds:

1. As cyanoalkanes: 2. As nitriles:

1. The root name is based on the 1. The root name is based on the
longest chain containing the cyano longest chain including the carbon
group. of the nitrile group.

2. This root give the alkane part of 2. This root give the alkyl part of
the name. the name.

3. The chain is numbered so as to 3. A –nitrile suffix is placed

give the cyano group the lowest directly after the alkane part.
possible number.

4. Since the nitrile must be at the

4. The cyano- prefix is used in a end of the chain, it must be C1 and
very similar manner to haloalkanes. no locant needs to be specified.

5. The cyano group takes 5. Cycloalkanes are followed by

precedence after acyl halides and the word –carbonitrile.
amides, but over aldehydes and
ketones, in the naming and
numbering of the root chain.

6. The cyano nomenclature is

most common when the alkyl group
is simple.
Example #1: Nitriles with aromatic ring Example #2: Nitriles with a
saturated hydrocarbon

benzonitrile

2-Methylcyclohexanecarbonitrile

Example #3: Nitriles with unsaturated aliphatic hydrocarbon

3-hexenenitrile
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