Aldehydes,

ketones,
carboxylic acids,
and derivatives of carboxylic acids

Aldehydes and ketones

An aldehyde is an organic compound containing carbonyl group >C=O bonded to one, or two
hydrogens.
O
C

O
C H

CHO

aldehyde group

carbonyl group
(found in aldehydes and ketones)

O
H C H

or

O
R C H

methanal
(formaldehyd)

O
Ar C H
any other aldehyde

A ketone has a carbonyl group bonded to two alkyls groups, or to two aryl groups, or one of each. A ketone does
not contain a hydrogen bonded to the carbonyl group.

O
R C R

O
Ar C Ar

dialkyl aldehyde

diaryl aldehyde

O
Ar C R
aryl alkyl aldehyde

Aldehydes and ketones (cont.)

Aldehydes and ketones are common naturally occurring compounds.
O
CH

H3C O
HO

vanillin
(in vanilla beans)

benzaldehyd
(in oil of bitter almonds)

CH3 O
CH

H3C

CH3

citral
(in lemon grass)

H
C C
H H

O
CH

H3C

H3C

cinnamaldehyde
(in cinnamon)

H3C

CH3

camphor
(camphor trees)

O
C H

O
H3C

OH
OH

O
cortisone
(andrenal hormone)

The word aldehyde was coined by as a contraction of the Latin alcohol dehydrogenatus
(dehydrogenated alcohol). The term formyl group is derived from the Latin word formica = ant. This
word can be recognized in the simplest aldehyde, formaldehyde (methanal), and in the simplest
carboxylic acid, formic acid (methanoic acid, an acid, but also an aldehyde).

Structure and bonding in aldehydes and ketones

The carbon in >C=O group is sp2 hybridized and forms three sigma () bonds that lie in a plane.
The bond angle between two the sigma bonds is approximately 120O. In the C=O group, one of the
atoms bonded to the carbon by a sigma bond is an oxygen atom. The carbon and the oxygen are
also jointed by pi () bond.

e drawn toward positive oxygen

O
C

OH
+ H

Because oxygen is more electronegatively than carbon, a C=O

bond is polar. The >C=O bond in a carbonyl group, with its and
electrons is more polar than the C-OH bond in alcohols. The
reason for this is that the electrons of the carbonyls pi () bond
are farther from the nuclei, less tightly held, and more easily
polarized. The carbonyl oxygen has an unshared lone pair of
valence electrons that can react with the proton to increase the
positive charge on the carbonyl carbon. Protonation is important in
many reactions of >C=O group.

Physical properties of aldehydes and ketones

Because aldehydes and ketones do not contain H-O bonds they cannot undergo hydrogen
bonding as do alcohols. On the other hand, they are polar and can form relatively strong
electrostatic attractions between molecules, the positive portion of one molecule being attracted
to the negative portion of another.

electrostatic attraction

For this reason, aldehydes and ketones have boiling points

intermediate between those of hydrogen-bonded compounds and
unpolar compounds

CH3CH2CH2-CH3
Bp, oC
R

C
R'

R''

hydrogen bond

C
R'

-0.5

CH3CH2 CHO

CH3CH2CH2-OH

49

97

Increasing boiling point

Although pure aldehydes and ketones cannot form hydrogen

bonds, these compounds can form hydrogen bonds with the
hydrogen of water and or alcohols. Because of this type of
hydrogen bonding, the water solubility of aldehydes and ketones is
parallel that of alcohols. Ethanal and acetone are miscible with
water. Butanone and butanal are partly soluble in water.

Tautomerism of aldehydes and ketones

An aldehyde or a ketone with at least one alpha () carbon hydrogen is in equilibrium with an enol
form an isomer that contains a >C=C< bond (- en) and a hydroxyl group (-ol).
-hydrogen

H O
C C

O H
C C

aldehyde
or keto form

enol form

H
O
CH2 CH

CH2

OH
CH

-carbon
acetalaldehyde

enol form

These structures are a special type of isomers called tautomers (Greek tautos the same).
The enol tautomer differs from the aldehyde or keto tautomer in the location of the double bond
and hydrogen. For tautomerism to occurs, a stucture must contain a double bond to a
heteroatom (an atom other than carbon, usually oxygen or nitrogen) and hydrogen. Most
simple aldehydes and ketones exist predominantly in the aldehyde or keto form.
hydrogen bond

O
H3C

O
CH3

2,4-pentadione
( -diketone)

H3C

O
CH3

Most simple aldehydes and ketones exist predominantly in

the aldehyde or keto form. In acetone only 3 molecules
would exist in enol form for every million molecules in keto
form. In some 1,3-diones (-diketones) containing another
-carbonyl group, the enol form is stabilized by
intermolecular hydrogen bonding. Because of stabilization
of enol form, 2,4-pentanedione exists as an equilibrium
approximately 80% enol and only 20% dione.

Nomenclature of aldehydes and ketones

Aldehydes. In IUPAC system, simple aldehydes are named after the parent alkane with the -ane
ending changed to -anal (-an for a saturated chain and -al for aldehyde). The carbonyl carbon in
a simple aldehyde must be carbon 1. Therefore, this number is omitted in the name. Other
substituents, such as alkyl branches, are named by prefixes in the usual manner.
CH3 CH2 CH2 CHO
CH3
4

CH3
O
CH CH2 CH
3

carbonyl carbon
is carbon 1

3-methylbutanal

Common aldehydes are often called by their trivial names. Many of these names are derived
from trivial name of corresponding carboxylic acids. Some of these names, such as
banzaldehyde, are accepted by the UIAP.

CH3

O
COH

acetic acid

CH3

O
CH

acetaldehyde

O
COH
benzoic acid

O
CH
benzaldehyde

Nomenclature of aldehydes and ketones (cont.)

With trivial names, Greek letters alpha (), beta (), gamma (), and so forth are used instead of
numbers to denote the position of substituent. The alpha carbon is the one bonded to the
carbonyl (>C=O) group, and the beta carbon is the next in line. The Greek letters are not used in
IUPAC names, only in trivial names

CH3CH2

O
COH

IUPAC:

Propanal

trivial:

Propionaldehyde

O
CH3CH COH
Cl
2-chloropropanal

ClCH2CH2

O
COH

3-chloropropanal

-chloropropionaldehyde-chloropropionaldehyde

Nomenclature of aldehydes and ketones (cont.)

Ketones. In the IUPAC system, simple ketones are named with the ending anone.
Most ketones names require a position number to specify the location of the >C=O group.
Because it can be at different positions within the carbon chain.
CH3

O
CCH2CH2CH3

CH3CH2

O
CCH2CH3

3-pentanone

2-pentanone

O
cyclohexanone
( no number needed)

Several types of trivial nomenclature systems for ketones are used. The simplest system is
naming the two groups bonded to >C=O group and adding the word ketone.
methyl

CH3

Other common names:

ethyl

O
C

CH2CH3

methyl ethyl ketone

Nomenclature of aldehydes and ketones (cont.)

Other common names:
aceto group
phenone group

O
CH3CCH3

O
CH3C

acetone

acetophenone

O
C
benzophenone

The Greek letters alpha () and alpha prime () are used to denote substituent positions in the
trivial names of some ketones. One alpha carbon is designated as carbon in order to
differentiate them

O
Cl2CHCCH3

O
ClCH2CCH2Cl

IUPAC:

1,1-dichloro-2-propanone

1,3-dichloro-2-propanone

trivial:

-dichloroacetone

'-dichloroacetone

Some important aldehydes and ketones

Formaldehyde (methanal, H2C=O) is a flammable, colorless, toxic gas with suffocating odor. It
is prepared commercially by the oxidation of methanol. A 37% water solution of
formaldehyde is known as formalin and used as an insecticide, as a fumigant; in embalming
fluid; and in manufacture of explosives, resins, plastics, fabrics, dyes, etc.
When aqueous solution of methanal is concentrated, a white polymer called
paraformaldehyde is formed. It is used as a disinfectant and in manufacturing.
n

H
C O

C O C O C O

paraformaldehyde

Acetadehyde (CH3CH=O) is flammable, colorless, water-soluble liquid with a pungent odor. The
vapors of this compound are narcotic and toxic irritant, If in large doses these vapors care inhaled,
death can occur by respiratory failure. Acetaldehyde is used in manufacture of dyes, plastics,
synthetic rubber. It can be polymerized to a cyclic compounds, paraldehyde and metaldehyde.
O
3 or 4 CH3CH

CH3
H3C

O
O

CH3
O

CH3
paraldehyde
( hypnotic)

H3C
or

O
O
O

CH3

H3C
metaldehyde
( used as a snail poison)

Some important aldehydes and ketones (cont.)

Acetone, (CH3)2C=O) is a colorless, volatile, flammable liquid with the sweet pungent odor. It is
prepared by oxidation of propan-2-ol. Acetone is relatively nontoxic, it is miscible with water and
the most other organic solvents, and it can dissolve most organic compounds. It is widely used as
solvent.
The breath and urine of a person with uncontrolled diabetes sometimes smell of
acetone. In the body cells, acetone arises from acetoacetate ion in the case when glucose cannot
be properly utilized by the bodys cells.
Methyl ethyl ketone (MEK, butan-2-one), is less water soluble and higher boiling than acetone.
Methyl ethyl ketone is used as a solvent and in the synthesis of other chemicals.

Preparation of aldehydes and ketones

Aldehydes. In laboratory an aldehyde is prepared by oxidation of a primary alcohol. Most
oxidizing agents cannot be used because they also oxidize aldehydes to carboxylic acids.
Middle oxidizing agents (as chromic oxide-pyridine complexes) convert primary alcohols to
aldehydes without oxidizing the aldehydes to carboxylic acids.

RCH2OH

O
RCH

Ketones. The most common method for ketone preparation is the oxidation of secondary alcohol.
Almost any strong oxidizing agent can be uses such as ; chromic oxide (CrO3), sodium dichromate
(Na2Cr2O7) or potassium permanganate (KMnO4).
OH
RCHR'
secondary
alcohol

O
RCR'
ketone

Diaryl ketones (ArCOAr) and aryl alkyl ketones (ArCOR)

are prepared by Friedel-Crafts acylation reaction the
reaction of benzene or other aromatic compound with an
acid chloride.
O
+ CH3CCl
benzene

acid chloride

AlCl3

O
CCH3
acetophenone

Reactions aldehydes and ketones

Reagents can add to a carbonyl double bond. Carbonyl compounds can undergo
hydrogenation. In this reaction aldehyde is reduced to1o alcohol, while a ketone is reduced to 2o
alcohol.
General reaction

O
C

R'

aldehyde or
ketone

H
H

catalyst

OH
R C H
R'
primary or
secondary alcohol

A carbonyl group >C=O is polar and can be attacked by either a nucleophile at the carbonyl
carbon or an electrophile at the carbonyl oxygen.

O
C

Nu

Addition of water
Addition of water is reversible reaction. Only the most reactive aldehydes, such a formaldehyde
or chloral (Cl3CCH=O) form stable hydrates.
O
HCH

O
RCR' +

H+

OH
HCH

H2O

OH
HCH
H OH

OH
HCH
OH
stable hydrate in solution

OH
RCR'
OH

H2O

-H+

non stable

Addition of alcohol. Alcohol are weak electrophiles, and trace of acid is necessary to catalyze
the reversible reaction. The product of the addition 1 mole of aldehyde is a hemiacetal, a
compound with one OH and OR on one carbon. A hemiacetal reacts further with an alcohol to
yield an acetal, a compound in which two OR groups are bonded to one carbon.
O
RCH +

R'OH

OH
RCH
OR'
hemiacetal

R'OH

OR'
RCH
OR'
acetal

This reaction is reversible, and the equilibrium lies of the aldehyde side of the equation.

Addition of alcohol to ketone

For the less reactive ketones , the equilibrium favors the carbonyl side of equation even more.
O
RCR' +

OH
RCR'
OR',

R''OH

OR''
RCR'
OR''

R''OH

ketal

hemiketal

Above equilibriums favor the aldehyde. However, if a five-membered ring or six-membered ring
cyclic hemiacetal or acetal can be formed, the cyclic product is favored. Cyclic product can be
obtain by addition an 1,2-ethanediol to aldehyde.
O

O
RCH +

HOCH2CH2OH

Monosaccharides (polihydroxy aldehydes or ketones) are in equilibrium with their hemiacetals

and hemiketals in solution.
aldehyde

CH2OH
H
OH

H
OH

OH
H
H

H
C O
OH

OH

hemiacetal group

CH2OH

cyclization of glucose

O
H
OH

OH

CHOH

Addition of hydrogen cyanide

Hydrogen cyanide (HCN), a toxic liquid or gas at RT, is very weak acid. In the
presence of CN- , HCN adds to the >C=O group of an aldehyde or ketone to yield
cyanohydrin, a compound with OH and CN bonded to the same carbon.
O
RCR +

OH
RCR
CN

HCN

CN

aldehyde
or ketone

-OH and -CN

on the same carbon

cyanohydrin

Cyanohydrins are found in nature. For example, the millipede (many-legged arthropod) carries the
cyanohydrin mandelonitrile in defensive gland. When this millipede is attacked , the mandelonitrile
is decomposed enzymatically to a mixture of benzaldehyde and HNC, which is squirted at the
predator. A single millipede can produce sufficient HCN to kill a mouse.
OH
CH CN

mandelonitrile

enzyme

O
CH

+ HCN

Addition-elimination reactions of aldehydes and ketones

Compounds that contain NH2 groups such as primary amines (RNH2 or ArNH2) and
hydrazines (-NH2, ArNH-NH2, etc.) can undergo addition reactions with aldehydes and ketones.
However, the addition products are unstable and undergo elimination of water.
O
R C R

OH
R C R
H N R'

+ H2N R'

addition product
( unstable)

OH
R C R
NR'

- H2O

elimination product

If ammonia is one of the reactants, the product is called an imine. If primary amine is one of the
reactants, the product is also called an imine but is frequently referred to as a Schiff base.
O
CH

+ H2NCH3
methylamine
0

a 1 amine

H , addition

OH
- H2O
CH
elimination
NCH3
H

CH
NCH3
imine
or Schiff base

A variety of NH2 can react with aldehydes and ketones. In the next slide just two examples will be
show.

Addition-elimination reactions of aldehydes and ketones (cont. )

The product of the reaction of hydroxyamine (HO-NH2) with aldehyde or ketone is
called an oxime.
O
CH3CCH3 +

H2N OH

NOH
CH3CCH3 +

H2O

oxime

When a hydrazine (R-NHNH2) reacts with an aldehyde or a ketone the product is a hydrazone.
O
CH3CCH3

H2NNH
phenylhydrazine

NNH
CH3CCH3
phenylhydrazone

Tollens test
Many tests for aldehydes are based on their ease of oxidation. The Tollens test is base on the
oxidation of an aldehyde with a solution of Ag+ ions, a very weak oxidation agent. If an aldehyde
is present, the product are the carboxylate and silver metal. The Ag metal forms a black
precipitate; or, if reaction vessel is clean, the silver plates on the glass to form a silver mirror.

O
RCH

+
2Ag(NH3)2

+ 3HO

O
RCO + 2Ag + 2H2O + 4NH3

Tollens reagent

O
RCR

+ 2Ag(NH3)2+ + 3HOTollens reagent

silver
mirror

no reaction

Fehling test
The Fehling test depends on the oxidation of an aldehyde by copper(II) ions. In
this test, the deep blue color of Cu2+ changes to a red precipitate of Cu2O.

O
RCH

2Cu

2+

blue

5OH

O
-

RCO

Cu 2O
red

3H2O

Carboxylic acids
A carboxylic acid is a compound containing the carboxyl group, a term derived from carbonyl
and hydroxyl. The carboxyl group is written in different manners.
C

O
COH

O
OH

COOH

CO2H

The group bonded to COOH can be almost any grouping, even another carboxyl group.
CH3COOH

COOH

acetic

CH2

H
CCOOH

HOOC COOH

acrylic

benzoic

oxalic

acid

In COOH group each oxygen atom carries two pairs of unshared valence electrons. These oxygen
atoms are electronegative with respect to the carbonyl carbon and the hydroxyl hydrogen. Thus,
the COOH is polar. Because of polarity of the O-H bond and because carboxylate ion (RCOO- ) is
resonance stabilized, carboxylic acids can lose a proton to a strong or moderate strong base
unshared valence electrons

polar bonds

O
R

C
O

Physical properties of carboxylic acids

A carboxylic acid molecule contains an OH group and thus can form hydrogen bonds with water.
Because of hydrogen bonding, the carboxylic acids containing one to four carbons are miscible
with water. Many of those with the larger number of carbons are partially soluble.
hydrogen bond from carbonyl oxygen to water

O
R C
O H

H
H O
O
H

hydrogen bond from hydroxyl oxygen to water

H O
O
C R
R C
O H O
carboxylic acid
dimer

Carboxylic acids also hydrogen

bond with other carboxylic acid molecules by
forming two hydrogen bonds between the two
carboxyl groups. In non-hydrogen-bonding
solvent, carboxylic acids exist as pairs of
associated molecules called dimers (two
parts).
Because of the strong attractions between
carboxylic acid molecules in the dimer form,
the melting points and boiling points of these
compounds are relatively high higher even
than those of comparable alcohols.

Physical properties of some carboxylic acids

Formula

IUPAC name

Mp (oC)

Bp (oC)

HCOOH

methanoic

101

CH3COOH

ethanoic

17

118

CH3CH2COOH

propanoic

-22

141

CH3CH2CH2COOH

butanoic

-5

163

CH3CH2CH2CH2COOH

pentanoic

-34

187

benzoic

122

250

COOH

Nomenclature of carboxylic acids

The IUPAC name of simple carboxylic acid is taken from the name of the parent alkane with
the ane ending changed to -anoic acid. The carbonyl carbon is numbered as carbon 1.
3

CH3CH2COOH
propanoic acid

CH3
CH3CHCOOH
3

2-methylpropanoic acid

The low-formula-weight carboxylic acids are usually referred by their trivial names, which often
are derived from the acids source or odor.
The name formic acid is derived from the Latin word for ants formica. At one time, this acid was
prepared by the distillation of red ants. The name acetic acid is derived from the Latin acetum,
i.e. vinegar. Vinegar is a 5-6% aqueous solution of acetic acid. Butyric acid is a principal
odorous ingredient of rancid butter. Valeric acid ( Latin valere to be strong) is not a strong
acid but is a very strong-smelling acid. Of the particular interest are the trivial names of the 6-, 8-,
and 10-carbon acids, which are foul-smelling compounds found in goat sweat. The name of all
three acids are derived prom the Latin caper, means goat. Enanthic acid is derived from the
Greek oenanthe vine blossom. Pelargonic acid is derived from its name of its ester found in
geranium Pelargonium roseum. (see next slide).
The name and properties some of important class of carboxylic acids fatty acids will be
discussed in lecture entitled LIPIDS

Trivial names and derivations of some carboxylic acids

Number
of C

Formula

Name

Derivation

HCOOH

formic

Ants (L. formica)

CH3COOH

acetic

Vinegar (L. acetum)

CH3CH 2COOH

propionic

Milk, butter (Gr. protos- first; pion fat

CH3(CH2 )2COOH

butyric

Butter (L. butyrum)

CH3(CH2 )3COOH

valeric

Valerian root (L. valere- to be strong)

CH3(CH2 )4COOH

caproic

Goat (L. caper)

CH3(CH2 )5COOH

enanthic

(Gr. oenanthe- vine blossom)

CH3(CH2 )6COOH

caprilic

Goat

CH3(CH2 )7COOH

pelargonic Its ester is found in the geranium

Pelargonium roseum

10

CH3(CH2 )8COOH

capric

Goat

Nomenclature of carboxylic acids (cont.)

Greek prefixes (, , , etc.) can be used to indicate a substituentss position in reference to
carbonyl group. These Greek prefixes are used only in trivial name. In the IUPAC system only
numbers are used.
Cl
CH3CHCH2COOH

OH
CH3CHCOOH
IUPAC;
Trivial;

2-hydroxypropanoic acid
-hydroxypropionic acid
(also called lactic acid, L. lac -milk))

3-chlorobutanoic acid
-chlorobutyric acid

When a COOH is bonded to a ring carbon, the cyclic portion of the molecule is named and the
ending carboxylic acid is added. Substituted benzoic acid are named in the same fashion as
other substituted benzenes, with benzoic acid as a parent name.
Carbon 1

COOH

H2N

COOH

OH
2-hydrxycyclohexanecarboxylic acid

4 aminobenzoic acid

Nomenclature of carboxylic acids (cont.)

A diacid is named as an anedioic acid in the IUPAC system. (The alkane e- is retain before a
consonant). The trivial name of these compounds are more frequently encountered than the
IUPAC names.

Formula

IUPAC name

Trivial name

HOOC-COOH

ethanedioic

oxalic

HOOC-CH2-COOH

propanedioic

malonic

HOOC-(CH2)2-COOH

butanedioic

succinic

HOOC-(CH2)3-COOH

pentanedioic

glutaric

HOOC-(CH2)4-COOH

hexanedioic

adipic

HOOC-(CH2)5-COOH

heptanedioic

pimelic

Preparation of carboxylic acids

Hydrolysis of carboxylic acid derivatives. Hydrolysis means cleavage of a molecule by water.
(From the Greek: hydro- meaning water and lysis means loosing or breaking). A compound
that yield carboxylic acid when it is hydrolyzed is called derivative of a carboxylic acid.
Derivatives of carboxylic acids
O
R C Cl
acid
chloride

O
O
R C O C R
acid
anhydride

O
R C OR'
ester

O
R C NH2
amide

R C N
nitrile

The >C=O group of carboxylic acid derivative (except nitriles) has two bonds. One of these
bonds is to a hydrogen, an alkyl group, or an aryl group. The other bond is to an electronegative
atom: X, O, or N).
When the derivatives is heated in aqueous acid
or base, he electronegative atom can be cleaved
carbonyl portion of the
electronegative atom
from the carbonyl carbon. If the cleavage is
derivative contains
H, R, or Ar bonded
O
carried out in acidic solution, the carbonyl
to the caronyl group
portion of the acid derivative is converted to a
R C OR'
carboxylic acid. If the reaction is carried out in
base, the carbonyl portion forms a carboxylate
ion. Carboxylates can be converted to carboxylic
acid by acidification.

General reaction for hydrolisis

In acid:
O
R C Y

H+

H OH

O
R C OH

H Y

carboxylic
acid

In base:

O
R C Y

O
R C O-

OH

carboxylate

O
R C OH

H Y

Preparation of carboxylic acids

Oxidation of primary alcohols and aldehydes. Strong oxidizing agents (CrO3, KMnO4) convert
primary alcohols and aldehydes to carboxylic acids.
R C OH

O
R C OH

CH
O

COH
O

Oxidation of an alkene containing one hydrogen on one of the double-bond carbons (=C-R)
yields a carboxylic acid.
COOH
COOH
hexene

hexanedioic acid

Oxidation of an alkylbenzenes yields aromatic carboxylic acid. Aromatic rings without

alkyl side chains are not easily oxidized.
O
CH3
N

COH
N
nicotinic acid
B vitamin

Acidity of carboxylic acids

The strength of an acid is expressed as the acidity constant Ka. Ka values are often converted to
pKa values, where pKa = -log Ka.
Formula

Acidity constants of some carboxylic acids

Name
Ka

pKa

HCOOH

formic

1.8 x 10-4

3,75

CH3COOH

acetic

1.8 x 10-5

4.74

CH3CH2COOH

propanoic

1.3 x 10-5

4.87

CH3(CH2)2COOH

butanoic

1.5 x 10-5

4.81

ClCH2COOH

chloroacetic

1.4 x 10-3

2.85

Cl2CHCOOH

dichloroacetic

3.3 x 10-2

1.48

Cl3CCOOH

trichloroacetic

2.0 x 10-1

0.70

CH3CHClCOOH

2-chloropropanoic

1.5 x 10-3

2.83

ClCH2CH2COOH

3-chloropropanoic

1.0 x 10-4

3.98

Ka
pKa

10-5

10-2

100

102
0

103
-2

Increasing acid strength

-3

Salts of carboxylic acids

Strong base such as NaOH undergo complete reaction with carboxylic acids to yield salts called
carboxylates.
O
R C O H

NaOH

O
R C O Na

HOH

Carboxylates are salts and behave much like inorganic salts. They are odorless, relatively high
melting, and often water soluble. Being ionic, they are insoluble in organic solvents. The sodium
and potassium salts of longhydrocarbon-chain carboxylic acids (fatty acids) are called soaps.
Carboxylates are named similarly to inorganic salts. The cation is first, followed by the name of the
anion as a separate word. The name of the carboxylate anion is taken of the parent carboxylic acid
with the oic acid ending changed to oate.
COOH
benzoic acid

COONa
sodium benzoate

Carboxylic acid also react with ammonia and amines to yield ammonium carboxylates. This
reaction is especially important in protein chemistry, because the protein molecules are rich in
carbonyl group and amino groups. Treatment of carboxylate with a strong or moderate strong acid
converts the salts back to the carboxylic acids.

Other reactions of carboxylic acids

Carboxylic acids are not reduced by catalytic hydrogenation. Other unsaturated groups in a
molecule can be reduced without concurrent reduction of COOH group.
keto group reduced

O
O
CH3CCH2COH +

carbonyl group not reduced

OH
O
CH3CHCH2COH

H2

Carboxylic acid are readily reduced to primary alcohols with a very reactive reducing agent
lithium aluminum hydride, LiAlH4,. This reagent reduces other carbonyl group such a keto
groups but does not usually reduce C=C double bonds.
O
CH3CH2COH

LiAlH 4

OH
CH3CH2CH2

Esterification. The reaction of a carboxylic acid with an alcohol and a trace of strong acid catalyst
(H2SO4) yields an ester, RCOOR. The reaction is called an esterification.
General equation for esterification.
O
RCOH

R'OH

O
RCOR' +
ester

H2O