Carboxylic Acid Derivatives Flashcards
Acid Halide Nomenclature
Change -ic acid to -oyl halide
Acid Anhydride Nomenclature
Replace acid in the parent name with anhydride
Amides and Imides Nomenclature
Drop -ic or -oic acid and replace with -amide`
Carboxylic Ester Nomenclature
Change -ic or -oic acid to -ate
Nitrile Nomenclature
Change -ic or -oic acid to -onitrile
Acidity of amide and sulfonamide derivatives
Acetamide > Benzenesulfonamide > Succinimide > Phthalimide
Relative reactivity of carboxylic acid derivatives
Acid halide > anhydride > ester > amide
What group does not react with alcohols?
Amides
What is the product of an aldol reaction?
A beta-hydroxyaldehyde or a beta-hydroxyketone
Increasing leaving ability
X- > RCOO- > RO- > R2N-
Reagents for acid catalyzed hydrolysis of ester & amide
p-TsOH, H2O (above arrow)
heat, 180ºC (below arrow)
Reagents for base catalyzed hydrolysis of ester & amide
NaOH/H2O (above arrow)
heat (below arrow)
Reagents for acid catalyzed nitrile hydrolysis
2 eq. H2O
H2SO4
THEN ON ARROW: H2O and heat
Reagents for base catalyzed nitrile hydrolysis
NaOH, H2O
heat
Reagents for acid halides with alcohols
Hindered base. Et3N, Diisopropylethylamine, pyridine for example
Reagents for amides with alcohols
Acid (HCl/H2O)
Reagents for reductions of ethers (LAH)
1) LiAlH4, ether
2) H2O/HCl
Reagents for reduction of amides
1) LiAlH4
2) H2O
Reagents for reductions of ethers (DIBAL-H)
1) DIBAL-H, toluene, -78ºC
2) H2O/HCl
Reagents for reduction of nitriles
1) LiAlH4
2) H2O
Reactants in Claisen condensation
1) EtO-Na+
2) HCl/H2O
