Organic Chemistry Chapter 10 Part II Carboxylic Acids

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 C-N 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)