PREPARATION OF ACIDS

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PREPARATION OF ACIDS
CARBONYLATION OF ORGANOMETALLICS
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Hydrolysis of RCN

RCOO-
- NH3 (smell)
RCOOH
(no smell)
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EXAMPLE
a-hydroxy acid
CO2
a-hydroxy acid
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REACTION OF ACIDS
NUCLEOPHILIC ACYL SUBSTITUTION
Have not we seen this before?
Boring, boring, boring.
Please, no more!!! Give me Cell Bio, Genetics or
even Physics, but no more this!!!
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Acid Derivatives
acetamide
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Fisher Esterification
H
HOH
ALCOHOL
ACID
ESTER
NOTE IT IS AN EQUILIBRIUM REACTION
USE BENZENE AS SOLVENT AND STEAM DISTILLED THE
WATER FORMED
OR USE LARGE EXCESS OF ALCOHOL
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Prelude to Fisher Mechanism
Where does O18 end up in products?
IF IN ESTER, THEN CLEAVAGE OCCURRED AT O18-H
IF IN WATER, THE CLEAVAGE AT CARBONYL - O-18
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PRIME EXAMPLE OF ACID CATALYZED ACYL NUCLEOPHILIC
SUBSTITUTION
-HO18H
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EMIL FISHER
SECOND CHEMIST TO RECEIVE NOBEL PRIZE RANKED
AMONG TOP 10 SCIENTIST OF ALL TIMES
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CONVERSIONS OF ACIDS TO ACID CHLORIDES
Cl atom is easily eliminated in nucleophlic acyl
substitutions
CAN CONVERT TO ALL OTHER ACID DERIVATIVES AT ROOM
TEMPERATURE
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EXAMPLES
RNH2
R2NH
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ESTERIFICATION USING CH2N2
- N2
CONVERTS HIGHER-BOILING ACIDS TO LOWER
BOILING ALDEHYDES - GC/MS
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CLA (conjugated linoleic acid) - health-giving
properties

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REDUCTION OF ACIDLAH
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