HYDROLYSIS REACTIONS hydrolysis of esters

Hydrolysis of an Ester in Base protontransfers H-OH HO -NaOH... ACYLATION OF ENAMINES... acyl group was added Cl... MISCELLANEOUS REACTIONS OF ACID DERIVATIVES... Reduction of Esters...

HYDROLYSIS REACTIONS

C

R O R

O C

R OH + H2O + R O H

Hydrolysis requires strong acid or base and heating under reflux

… It’s not easy !

:

_ :

O C

R O R' O

R O R' O

H

_

:

: :

O C

R O R' O

H

_ :

: :

O C

R O R' O

H

_

:

: : O C R O

H :

O R' :

+

R C O

O :

_

O R' H

+

_

Hydrolysis of an Ester in Base

protontransfers

H-OH

HO

-NaOH

:

O C

R O R' H

H O H

:

O C

R O R' O

R O R' O

R O R' O

H H

H

O C

R O R'

O H

H H

:

+

:

O C

R O R'

O H

H H

:

C R O H

H

:

O R' H

: +

+

O C

C

R NH2

O C

Hydrolysis requires strong acid or base and heating under reflux

… It’s not easy !

+ : NH 2

_ O

C R

O H

O C

Base-Promoted Hydrolysis of a Amide

MECHANISM

stronger base than OH-, but this step doesn’t reverse because

of the next one

once in

a while

most often this step reverses because OH - is

a better leaving group than NH2-

accumulates

NaOH

ACYLATION OF ENAMINES

R R

CH C R

N C

R R

R

O

+

N H

H 3 O+

Acylation of an Enamine

acyl group was added

Cl

O

N C R

C R R

C

O R

… continued

slow

enamine

iminiumsalt

N H

N C

C C

H

: +

Acylation of an Enamine Mechanism (cont)

N C C C R

:

+

N H

: :

C C

H

O H

H +

C C R

N

+ H 2 O

MISCELLANEOUS REACTIONS OF ACID DERIVATIVES

Reduction of Esters

+ R' OH

Reduction of Esters to Aldehydes

DIBALH toluene -78°C

H 2 O HCl

REACTIONS AND SYNTHESIS

C N R

O H :

_ C R

N OH

NH OH

:

NH 2 O

+ : NH 2

_ O

C R

O H

O C

Base-Promoted Hydrolysis of a Amide

: + C N

O H H

: +

C N

O H H

:

C N R

O H

H H

: +

H-OH2+

H2SO4 / H2O

:

+ O C

R NH 2

H

O H H :

:

+

O C

R NH 2

H

O H H :

:

+

O C

:

+

O C

R NH 3

H

O H :

:

+

O C

R OH + NH + 4

: +

:NH 3 +

Acid-catalyzed Hydrolysis of a Amide

FATS AND OILS

C OH (CH 2 ) 10

CH 3

O

C OH (CH 2 ) 12

CH 3

O

C OH (CH 2 ) 14

CH 3

O

C OH (CH 2 ) 16

CH CH

CH

CH 2

CH 3

The Fatty Acids

Lauric acid Myristic acid Palmitic acid

Stearic acid Oleic acid

Linoleic acid

Linolenic acid

CH 2 C

CH 2

H O

C R

Each acyl group can come from

a different fatty acid chain.

fatty acid 1

fatty acid 2

fatty acid 3glycerol

C C C

H O

CH2C

CH2

H OH

OH

O H ONa

C R

OOC

COO OOC

COO OOC

-

-grease particle

O H H

O H H

O H H

O H

H

O H H

O H H

O H H

O H H

O H H

O H H

O H H