HYDROLYSIS REACTIONS

1
HYDROLYSIS REACTIONS
2
Hydrolysis of Esters
Basic Solution
Na
Na
heat
Acidic Solution
heat
excess
Hydrolysis requires strong acid or base and
heating under reflux.
.. Its not easy !
3
Hydrolysis of an Ester in Base
NaOH
H-OH
proton transfers
-
HO
4
Hydrolysis of an Ester in Acid
H2SO4 / H2O
H3O

H-OH2
proton transfers
OH2
H3O
5
Hydrolysis of Amides
Basic Solution
Na
Na
heat
Acidic Solution
heat
excess
Hydrolysis requires strong acid or base and
heating under reflux.
.. Its not easy !
6
Base-Promoted Hydrolysis of a Amide
MECHANISM
NaOH
most often this step reverses because OH- is a
better leaving group than NH2-
stronger base than OH-, but this step
doesnt reverse because of the next one
once in a while
accumulates
7
ACYLATION OF ENAMINES
8
Acylation of an Enamine
..
-
Cl
acyl group was added
9
Acylation of an Enamine Mechanism
iminium salt
slow
enamine
..
.. continued
10
Acylation of an Enamine Mechanism (cont)

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SUMMARY OF ACYLATION
enamine
acyl group
12
MISCELLANEOUS REACTIONS OF ACID DERIVATIVES
13
Reaction of Esters with Organometallic
Reagents
cleaves the ether .
reacts twice !
14
Reduction of Esters
15
Reduction of Esters to Aldehydes
16
NITRILES
REACTIONS AND SYNTHESIS
17
Formation of Nitriles
SN2 Reaction
Addition to CO
..

pH 6
cyanohydrin
18
Hydrolysis of Nitriles
ACID SOLUTION
BASIC SOLUTION
Acid or Base
19
Base-Promoted Hydrolysis of a Nitrile
MECHANISM
NaOH
1)
2)
3)
amide
.. continued
20
Base-Promoted Hydrolysis of a Amide
MECHANISM
NaOH
4)
5)
6)
21
Acid-catalyzed Hydrolysis of a Nitrile
MECHANISM
1)
2)
H2SO4 / H2O
3)
H-OH2

protonated amide
.. continued
22
Acid-catalyzed Hydrolysis of a Amide

..
H-OH2
..
4)
OH2
5)
6)
23
FATS AND OILS
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The Fatty Acids
25
The Triacylglycerols
glycerol
fatty acid 2
fatty acid 3
fatty acid 1
Each acyl group can come from a different fatty
acid chain.
26
SAPONIFICATION
SOAP
NaOH
(lye)
heat
SOAP
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MICELLE
grease particle