Carboxylic Acid Derivatives Flashcards
1
Q
What’s the most reactive COOH derivative?
A
Acyl halides, specifically with Cl
2
Q
How to reduce acyl halide to aldehyde without reducing all the way to alcohol?
A
Use bulky reagent with only one hydride (e.g. LiAlH(O-R)3
3
Q
How to decarboxylate an amide?
A
Hoffman rearrangement of amide to primary amine + loss of CO2. Amide + NaOH + Br2 = R-NH2. Has nitrene intermediate (6 e- N)
4
Q
Explain how to create ß-keto-ester from an ester
A
Claisen condensation. Simplest: 2 moles ethyl acetate react to form ethyl 3-oxobutanoate. Same mechanism as aldol condensation
5
Q
Describe ester reduction
A
LAH reduce an ester to two alcohols.
6
Q
What’s the most stable COOH derivative?
A
Amides. Extreme (acidic) conditions required to hydrolyze
