ESTERS

The general formula of esters

CnH2n + 1COOCmH2m+1 where n =0,1,2,3 and m = 1,2,3 The values of m and n in both the alkyl groups may be the same or different. When n=1, and m =2, the formula of ester is CH3 COOC2H5 ( ethyl ethanoate )

Esters are formed by the reaction between carboxylic acids and alcohols.
Hence, the general formula of esters is obtained by combining the general formulae of carboxylic acid and alcohol.

Removal of water molecule

Carboxylic acid

Alcohol

CnH2n+1 COH

CmH2m+1 OH

CnH2n+1 COCmH2m+1 + H2O

In and ester, the H in the carboxyl group is replaced with an alkyl group O

CH3 CO CH3 = CH3COO CH3 ester group

The functional group of ester

Is the carboxylate group

O

CnH2n+1 C O CmH2m+1

The molecular formula of esters can be written as CnH2nO2. The molecular formula of carboxylic acid is also CnH2nO2. This means that the esters and carboxylic acids that have the same number of carbon atoms are isomers.

Example :

Methyl methanoate (CH3COOCH3) is the isomer of propanoic acid (CH3CH2COOH) because both of the compounds have the same molecular formula that is C3H6O2.
C3H6O2
isomers

CH3COOCH3 Methyl ethanoate (ester)

CH3CH2COOH Propanoic acid (carboxylic acid)

Ester are also isometric with other esters. Example: Ethyl ethanoate (CH3COOCH2CH3) and methyl propanoate (CH3CH2COOCH3) are isomers.

Both of these esters have the same molecular formula that is C4H8O2.

Naming Esters

Derived from the alcohol and the carboxylic acid used to prepare it.
Consists of two parts.

First part

The name of the ester is taken from the alkyl group of alcohol. Example : a. methanol methyl b. ethanol ethyl c. propanol propyl

Second part

Is obtained by changing the oic on the name of carboxylic acid to oate.

Example : a. methanoic acid methanoate b. ethanoic acid ethanoate c. propanoic acid propanoate Hence, the ester prepared from ethanol and ethanoic acid is called ethyl ethanoate.

Naming Esters

Name the alkyl from the alcohol OName the acid with the C=O with ate acid alcohol O methyl CH3 CO CH3 methyl ethanoate (IUPAC) methyl acetate (common)

Ethanoate (acetate)

Some Esters and Their Names

Flavor/Odor Raspberries HCOOCH2CH3

ethyl methanoate (IUPAC) ethyl formate (common)

Pineapples CH3CH2CH2 COOCH2CH3 ethyl butanoate (IUPAC) ethyl butyrate (common)

O CH3 C O CH2 CH2 CH CH3 CH3

O CH3 CH2 CH2 C Ethyl butyrate pineapple O O CH2 CH CH3 CH3 CH3 C O CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3 O CH2 CH3

Isopentyl acetate banana O CH3 CH2 C

Isobutyl propionate rum O CH3 C O

Octyl acetate orange O

CH2 CH2 CH3

CH3 CH2 CH2 C Methyl butyrate apple

CH3

Propyl acetate pear

Learning Check
Give the IUPAC and common names of the following compound, which is responsible for the flavor and odor of pears.
O

CH3 CO CH2CH2CH3

Solution
O

propyl

CH3 CO CH2CH2CH3
propyl ethanoate (IUPAC) propyl acetate (common)

Learning Check
Draw the structure of the following compounds:
A.

3-bromobutanoic acid Ethyl propionoate

B.

Solution
A. 3-bromobutanoic acid Br |
CH3CHCH2COOH B. Ethyl propionoate O

CH3 CH2 COCH2CH3 CH3CH2COOCH2CH3

Name of some common esters together with the carboxylic acid and alcohol used to prepare them.

Name of ester Ethyl methanoate Methyl ethanoate Propyl ethanoate Ethyl propanoate Butyl methanoate Methyl butanoate

Formula of ester HCOOCH2CH3 CH3COOCH3 CH3COOCH2CH2CH2 CH3CH2COOCH2CH3 HCOOCH3CH2CH2CH3

Prepared from Ethanol + Methanoic acid C2H5OH + HCOOH Methanol + Ethanoic acid CH3OH + CH3COOH Propanol + ethanoic acid CH3CH2CH2OH + CH3COOH Ethanol + propanoic acid C2H5OH + CH3CH2COOH Butanol + methanoic acid CH3CH2CH2CH2OH + HCOOH Methanol + butanoic acid CH3OH + CH3CH2CH2COOH

CH3CH2CH2COOCH3

hydrogenation Alkene cracking hydration dehydration Oxidation Alcohol esterification Ester Carboxylic acid Alkane

The flow chart shows the interconversions of alkane, alkene, alcohol, Carboxylic acid and ester.

Preparation of ethyl ethanoate

Esterification

Reaction of a carboxylic acid and alcohol Acid catalyst O H+ CH3 COH + HOCH2CH3 O
CH3 COCH2CH3 + H2O

Hydrolysis

Esters react with water and acid catalyst Split into carboxylic acid and alcohol O H+ H COCH2CH3 + H2O
O

H COH

+ HOCH2CH3

Saponification

Esters react with a bases Produce the salt of the carboxylic acid and alcohol O CH3COCH2CH3 + NaOH
O
CH3CO Na+ + HOCH2CH3 salt of carboxylic acid

Learning Check
Write the equation for the reaction of propionic acid and methyl alcohol in the presence of an acid catalyst.

Solution
O
CH3CH2COH + HOCH3 O CH3CH2COCH3 + H2O H+

Learning Check
What are the organic products when methylacetate reacts with A. Water and an acid catalyst? B. KOH?

Solution
A.

CH3COH O

HOCH3

B.

CH3CO K+

+ HOCH3