ESTER

Organic Chemistry 2016

CARBOXYLIC ACID DERIVATIVES
 ESTER Nomenclature
• Functional class name = alkyl O
alkanoate
• Substituent suffix = -oate R C
Esters are alkyl derivatives of
OR'
carboxylic acids
• The first component of an ester
name, the alkyl is derived from the
alcohol
• The second component of an ester
name, the -oate is derived from
the carboxylic acid
 Physical Properties : Boiling point
• Like aldehydes and ketones, they are polar
molecules and so have dipole-dipole
interactions as well as van der Waals dispersion
forces. However, they don't form hydrogen
bonds, and so their boiling points aren't
anything like as high as an acid with the same
number of carbon atoms.
 Physical Properties : Solubility
• The small esters are fairly soluble in water but
solubility falls with chain length.

• although esters cannot form hydrogen bond with each

other, they can form hydrogen bond with water
molecules. One of the partially-positive hydrogen
atoms in a water molecule can be sufficiently attracted
to one of the lone pairs on one of the oxygen atoms in
an ester, forming a hydrogen bond.
 Other properties
• Esters are liquid at room temperature, even
when the molecular weight is high

• Carboxylic acids are noted for their sour,

disagreeable odors. On the other hand, esters
have sweet and pleasant odors often
associated with fruits, and fruits smell the way
they do because they contain esters.
No. Ester Aroma

1. Isoamil asetat Pisang

2. Etil asetat Penghapus cat kuku
3. Metil salisilat Tanaman wintergreen
4. Etil butirat Nanas
5. Benzil butirat Ceri
6. Etil propionat Buah-buahan
7. Etil benzoat Rum
8. Benzyl asetat Buah persik
9. Metil butirat Apel
10. Oktil asetat Jeruk
11. n-propil asetat Buah pir
12. etil fenilasetat Madu
 Chemical Properties
1. Carbonyl groups determine the reactivity of
ester
2. Nucleophilic substitution reaction of esters
are easily occured
 Preparation of Esters
• Esters are made by a condensation reaction between
carboxylic acid and alcohols in which a molecule of
water is eliminated. The hydroxyl group of the alcohol
reacts with the carboxyl group of the carboxylic acid
to eliminate the elements of water.

• This results in the formation of the ester link

(-COO-) between the two molecules.

• The making of an ester is called an

esterification reaction.
 Reactions :Hydrolysis
• An ester reacting with water, giving the
carboxylic acid and alcohol, is called
hydrolysis; it is acid catalyzed. The base-
promoted decomposition of esters yields an
alcohol and a salt of the carboxylic acid; this
process is called saponification. Saponification
means, “soap making,” and the sodium salt of
a fatty acid (e.g., sodium stearate) is a soap.

R—COOR’ + NaOH → RCOONa + R’OH

Saponification
 Transesterification
• When in ester is placed in a large excess of an
alcohol along with presence of either an acid
or a base there can be an exchange of alkoxy
groups.
• The large excess of alcohol is used to drive the
reaction forward. The most common method
of transesterification is the reaction of the
ester with an alcohol in the presence of an
acid catalyst
R—COOR’ + R’’OH RCOOR’’ + R’OH
High boiling point ester High b.p alcohol Higher b.p ester Lower bp alcohol
• The reaction between the alcohol and ester
produce a new ester with an alkyl group ( the
carbonyl oxygen ) from the new alcohol
• In this reaction, substitution of alkyl group
occurs in the ester carbonyl oxygen
 Example

O O
H+
CH3 C + CH3 CH2 OH CH3 C + CH3 OH
OCH3 OCH2CH3
metil asetat etanol etil asetat metanol
 Fats and Oils (as a big ester)
• Fats and oils are esters made when an alcohol,
glycerol (with 3 hydroxyl groups) condenses
with carboxylic acids known as fatty acids.
Glycerol (propane-1,2,3-triol) is a trihydric
alcohol.
• The reaction between three fatty acids and
glycerol is shown below. Each molecule of the
alcohol condenses with 3 molecules of fatty
acid.
OIL FAT
 Saturated fatty acid:

Unsaturated fatty acid: