Carboxylic Acids Deriva-tives other than Ester

Nanoplasmonic Research Group

Organic ChemistryChapter 10

Part II

Activated Acyl Com-pounds

- Focus on leaving group -• Acyl Halides Carboxylic acids with thionyl

chloride or phosphorus pen-tachloride

• 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 car-boxylic acid derivative

- Amide -• The reaction of a carboxylic acid

with an amine

• Planar geometry!!: rotation around the C-N bond is restricted due to resonance

• High boiling point

The Claisen Condensa-tion (I)

• Carbon-carbon bond forming reac-tion 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 Condensa-tion (II)

Summary (Reaction of Acid Derivatives)

The Claisen Condensa-tion (II)