Esters and Esterification

Esters produced by combining carboxylic acid andalcohol (esterification)

Large chain esters account for flavor and odor of fruits.

General formula: R–COOR'

R - hydrocarbon chain from the acid R' - hydrocarbon chain from the alcohol.

alcoholcarboxyl acid

H

C-C

O

O H O-C

ester

water

Esterification is a reversible reaction.

De-esterification reaction

esterification reaction

H

O

H

O-CC-C

O

+

ester

alcohol

carboxyl acid

H

C-C

O

O H

O-C

· First name alcohol: change "anol" to "yl"· Second name acid: change "ioc acid" to "oate"

Naming Esters

2 – names:

CH3COOCH2CH2CH3

propyl ethanoate

CH3-C

O

\O-CH2CH2CH3

//alcohol

acid

CH3CH2CH2CO + OCH3

butanoic acid methanol

CH3CH2CH2COOCH3 + H2O

methyl butanoate water

OH H

CH3CH2CH2CH2CH2COOCH2CH2CH2CH3

butyl hexanoate

Write the esterification reaction for the reactionbetween pentanoic acid and 1-butanol.

Esters are polar molecules but have NO hydrogen bonding (unlike alcohols, carboxylic acids, water)

Bp / mp are higher than aliphatics but lower than acids and alcohols.

Esters are soluble in water.

• Esterification carboxylic acid and an alcohol thatproduces an ester and water.

• General formula RCOOR' ( R acid, R' alcohol).

• Name is two words: the alkyl group from alcohol,then acid with replaced ending - oate.

• Polar but do not hydrogen bond. Lower melting points and boiling points than acids and alcohols.

• Soluble in water.

Hydroxide ions also catalyze the breakdown ofesters.

salt