ESTERS

 Structure of Esters
 Preparation of Esters
 Nomenclature for Esters
 Selected common Esters
 Isomerism for Esters
 Physical properties of Esters
 Chemical reactions of Esters
 Sulfur analogs of Esters
 Polyesters
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 Structure of

Esters
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 ESTER - is a carboxylic acid
derivative in which the –OH portion of
the carboxyl group has been replaced
with an –OR group.
O O
ll ll
R-C-O-H R-C-O-R

Functional group: O
ll
3 -C-O-R
 In linear form,
- COOR or – CO2R

The simplest ester

O
ll
H-C-O-CH3
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 Two three-carbon ester
O
ll
H-C-O-CH2-CH3

and
O
ll
CH3-C-O-CH3
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Structure of
simplest aromatic
ester

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 Difference between a carboxylic
acid and ester

O O
ll ll
R-C-O-H and R-C-O-R

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 Preparation of

Esters

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 Esterification Reaction

- is the reaction of a carboxylic

acid with an alcohol ( or phenol)
to produce an ester.

O O
ll   ll
R-C-O-H +¿ H-O-R’
 
R-C-O-R’ + H20
Carboxylic acid alcohol ester water
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 In the esterification process, a –OH
group is lost from the carboxylic acid, a
–H atom is lost from the alcohol, and the
water is formed as a by-product.

The net effect of this reaction is

substitution of the –OR group of the
alcohol for the –OH group of the acid.

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 reaction of acetic acid and
with methyl alcohol.

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 O
ll
R-C— ————O-R ’

Acid part Alcohol part

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 Cyclic esters
cyclic esters, like cyclic
ethers, are heterocyclic
organic compounds.

cyclic esters are formally

called lactones.
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