Organic Chemistry
Chapter 10
Part II
Carboxylic Acids Derivatives
other than Ester
Nanoplasmonic Research Group
Activated Acyl Compounds
- Focus on leaving group -
• Acyl Halides
Carboxylic acids with thionyl chloride
or phosphorus pentachloride
• Acid Anhydrides
Carbonylation of methylacetate or
dehydration of carboxylic acids
Acyl halides can react with..
• Water to form a carboxylic acid
• Alcohol to form an ester
• Amine to form an amide
Acid anhydrides can react with..
• Water to form a carboxylic acid
• Alcohol to form an ester
• Amine to form an amide
“The point is acid anhydride is more reactive
than ester, but less reactive than acyl halide
toward nucleophile”
The least reactive carboxylic
acid derivative
- Amide -
• The reaction of a carboxylic acid with an
amine
• Planar geometry!!: rotation around the CN bond is restricted due to resonance
• High boiling point
The Claisen Condensation (I)
• Carbon-carbon bond forming reaction that
occurs between two esters or one ester
and another carbonyl compound in the
presence of a strong base
• At least one of the reagents must be
enolizable
• The base used must not interfere with the
reaction (nonnucleophilic!!!!)
The Claisen Condensation (II)
Summary
(Reaction of Acid Derivatives)
The Claisen Condensation (II)