Saponification of Esters: Base Catalyzed Hydrolysis ... - Carbon Rules

Overall Reaction:
Saponification of Esters:
Base Catalyzed Hydrolysis of Esters
R
O
OR
1) NaOH
2) H 3 O + R
O
OH
ROH
Mechanism:
R
O
OR
OH
nuc
attack
R
O
OH
OR
loss of
leaving
group
R
O
O H
OR
R
O
O
ROH
To produce a carboxylic acid, H 3 O + must be added at the end. Why

How Soap Is Made
O
O
polar group
(hydrophilic)
non-polar group
(hydrophobic)
• Soaps are compounds that contain a polar group on
one end of the molecule and a non-polar group on the
other end.
• The hydrophobic tail surrounds oil molecules,
forming a micelle.
O
O
O
O
O
NaOH
OH
OH
OH
glycerol
Na
Na
O
O
O
O
O
O
A fat molecule
Na
O
Soap molecules
Base catalyzed hydrolysis gives glycerol and 3 soap molecules.