CARBOXYLIC ACIDS

The

simplest series of
carboxylic acids are the
alkanoic acids,
R-COOH,
where

R is a hydrogen or an
alkyl group.

NOMENCLATURE AND
STRUCTURE

Common name
Formic acid, found in insect stings
(formic from the Latin word meaning ant);
Acetic acid the principal component
of vinegar (Latin: Acetum, vinegar)
Butyric acid found in rancid (Latin:
butyrum, butter);
Caproic, caprylic, and capric acids found
in goat fat(Latin: caper, goat);
Palmitic acid (palm oil); stearic acids
(Greek: stear, tallow).

NOMENCLATURE AND
STRUCTURE

The systematic IUPAC nomenclature

for carboxylic acids requires the
longest carbon chain of the molecule
to be identified and the -e of alkane
name to be replaced with -oic acid.

Example
name

Common name IUPAC

HCOOH

formic acid

methanoic acid

CH3COOH

acetic acid

ethanoic acid

CH3(CH2)8COOH capric acid

CH3(CH2)14COOH

decanoic acid

palmitic acid

hexadecanoic
acid

Example
Common name
IUPAC name

CH3CH2CH CHCOOOH
| |
,-dimethylvalveric
dimethylpentanoic
CH3
CH3
acid

CH3CHCOOH

acid

-hydroxyproponoic acid

hydroxypropanoic acid

|
OH

2,3-

or lactic acid

2-

Aromatic Carboxylic acid

In which the carboxyl group is

attached directly to the benzene ring
(ArCOOH) are named as derivatives
of the parent acid, benzoic acid,
C6HCOOH.

Subtituents on the benzene ring are

designated either by number or by the
prefix ortho(o), meta(m), or para(p).
The carbon atom that bears the carbonyl
group in the ring is always number 1
when aromatic acid is named as a
substituted benzoic acid.

The ortho, meta, para positions are

indicated in the stucture of benzoic acid,
using the COOH group as point of
refernce.
Ex.
COOH
|
p
bromobenzoic acid
4
bromobenzoic acid
|
COOH
Br

The name of a salt of carboxyl acid

consists of the name of the cation
followed by name of acid with ending -ic
acid changed to ate.
Ex.
COONa
|
sodium
benzoate

(CH3COO)2Ca
or

calcium acetate
calcium

ethanoate

Nomenclature of
dicarboxylic acids
Example

Common name

IUPAC

name
HOOCCOOH

Oxalic acid

ethanedioic

acid
HOOCCH2-COOH

Malonic acid

propanedioic

acid
HOOCCH2CH2-COOH

Succinic acid

HOOCCH2CH2CH2-COOH

Glutaric acid

butanedioic acid
pentanedioic acid

HOOCCH2CH2CH2CH2-COOH hexanedioic acid

Adipic acid

SYNTHESIS OF CARBOXYLIC
ACIDS
Oxidation of primary alcohols

1.

Provides one of the most direct routes to the

corresponding aliphatic acids. This is
accomplished by use of KMnO4, K2CrO7, or
Na2Cr2O7.

CH3CH2CH2OH + (O)
CH3CH2COOH
CH3CH2CHCH2OH + (O)
CH3CH2CHCOOH
|

2. Carbonation of Grignard reagent

(Grignard synthesis)
Is

carried out by bubbling gaseous CO2

into the ether solution of the Grignard
reagent, or by pouring the Grignard
reagent on crushed dry ice (solid CO2).
This process has the special advantage
of increasing the length of a carbon
chain.
O

R-MgX + C=O
MgX2

O
ether

R-C-OMgX

H+ R-C-OH

CHEMICAL REACTIONS

The characteristic chemical behavior

of carboxylic acids is determined by
their functional group, carboxyl (COOH).
(C=O) carbonyl group
(-OH) - hydroxyl group

-OH group that actually undergoes

nearly every reaction loss of H+, or
replacement by another group but
it does so in away that possible only
because of effect of the C=O

1.

Salt formation
CH3COOH + Zn

(CH3COO)2Zn + H2

CH3(CH2)10COOH + NaOH
+ H2O

CH3(CH2)10COONa

2. Reduction to primary Alcohols

CH3CH2COOH
LiAlH4
CH3CH2CH2OH
CH3
CH3
|
|
CH2-C_COOH
CH OH

LiAlH4

CH3-C-

3. Alpha-halogentaion (Hell-VolhardZelinsky reaction)

When an aliphatic carboxylic acid is treated

with Cl2 or Br2 in the presence of red
phosphorus, the alpha-hydrogen atoms on
the carbon adjacent to the carboxyl group are
replaced by Cl or Br. By appropriate control of
reaction conditions, this reaction may be
caused to proceed stepwise to produce either
mo- or polyhalogented acid. After full
replacement of the alpha-hydrogen atoms,
however, no further halogenation occurs.

CH3CHOOH + Cl2
CH3CCLCOOH
|
CH3

red P

|
CH3

CARBOXYLIC ACID DERIVATIVES

Four important classes of acid
derivatives are formed by the
replacement of hydroxyl group
another atom or group of atoms.
Each of these derivatives contain the
acyl group, R C = O.
O
O
O
O
O

R-C-O-C-R
R-C-Cl
R-C-O-R
R-C-NH2

An acid anhydride

an acyl chloride

an ester

an amide

Acid anhyrides

1.

An acid anhyride can be thought of as the

result of removing one molecule of water
from two carboxylic acids groups.

O
O

RCOH + HOCR

RC O CR + H2O

Named by replacing the word acid in the

name of the parent acid with the word
ahydride. For example,
O
O
O

CH3COH
CH 3C O CCH3
Acetic acid

acetic anhydride

2. Acyl chlorides (Acid chloride)

Are structurally related to carboxyl acids by the
replacement of the OH group by a chlorine atom.
They are usually named by combining the stems
of the common names of carboxylic acid with
suffic yl and then the name of the chloride ion.
Ex.
CH3COCl
CH3CH2CH2COCl
acetyl chloride
butyryl chloride

3. Esters
A carboxylic acid is converted into an ester when
heated with an alcohol in presence of a little
mineral acid, usually concentrated H 2SO4 or dry
HCl.
Ester are nearly always called by their common
names. The name of the alkyl group in alcohl,
and then the common name of the acid with
ending ic acid changed to ate.

4. Amides
Are

compound in which the OH of the

carboxylic acid has been replaced by
NH2. they are named as derivatives of
the corresponding carboxylic acids, the
suffix amide being substituted for ic
acid or oic acid in the name of the
parent acid.

CH3CO NH2
CO NH2
Acetamide
benzamide

CARBOXYLIC ACIDS
Submitted by: Sherlene A. Gesim
Submitted to: Mrs. Elizabeth Vivar