Test III (Reagents) Flashcards
Acid-catalyzed hydrolysis of esters
Water
Acid (eg. HCl)
Acid hydrolysis of amides
Water
Acid (eg HCl)
Base hydrolysis of amides
Water
Base (eg NaOH)
Acid hydrolysis of nitriles
Water
Acid (eg HCl)
Base hydrolysis of nitriles
Water
Base (eg NaOH)
Acid Chloride + ____ -> Amide
Amine (eg NH3) OR R-NH2
Acid Chloride + ____ -> Ester
Alcohol (eg MeOH) OR R-OH
Acid Chloride + ____ -> Anhydride
Carboxylic acid
Anhydride + ____ -> Amide
Amine (eg NH3) OR R-NH2
Anhydride + ____ -> Ester
Alcohol (eg MeOH) OR R-OH
Reduction of esters (to primary alcohol)
Lithium aluminum hydride (LiAlH4) (H connects to middle)
Reduction of amides (to primary amines)
Lithium aluminum hydride (LiAlH4) (H connects to middle)
Reduction of nitriles (RCN) to primary amine
Lithium aluminum hydride (LiAlH4) (H connects to C)
Reduction of esters with Grignard reagents
Grignard reagent (eg. MeMgBr or PhMgBr)
Acid catalyzed bromination of α position
Br2
Acid (eg HCl)
Basic bromination of α position
Br2
Base (eg NaOH)
Bromination of α position of carboxylic acid
Br2
PBr3
Base-catalyzed aldol reaction
Base (eg NaOH)
Base-catalyzed cross aldol reaction
Base (eg. NaOH)
Additional carbonyl compound
Base aldol condensation + Heat + ____ -> α-β unsaturated carbonyl
Base (eg. NaOH)
Base cross aldol condensation + Heat + ____ -> α-β unsaturated carbonyl
Base (eg. NaOH)
Additional carbonyl compound
Acid-catalyzed aldol condensation + ____ -> α-β unsaturated carbonyl
Acid (eg. HCl)
Acid-catalyzed aldol cross condensation + ____ -> α-β unsaturated carbonyl
Acid (HCl)
Additional carbonyl compound
Claisen condensation
Base (eg NaOH)
Cross Claisen condensation
Base (eg NaOH)
Additional carbonyl compound
Alkylation of malonates with alkyl bromide
Alkyl bromide
Base (eg NaOH)
Knoevenagel condensation (aldol condensation of malonate with aldehyde)
Aldehyde
Base (eg NaOH)
Conjugate addition with ___ produces a β-nitrile carbonyl compound
Potassium cyanide
Conjugate addition with ____ produces a β-amino carbonyl compound
Amine
Basic conjugate addition of enolate/enol
Enolate
Acidic conjugate addition of enolate/enol
Enol
Direct addition (multiple options)
NaBH4 OR LiAlH4 (adds H)
OR R-Li (eg Me-Li) (adds R/Me)
OR -CN (reversible, adds -CN)
Conjugate addition
R2CuLi (eg MeCuLi, Mg2CuLi) (adds R/ME)
OR -CN (adds CN)