Orgo Exam 3 Mechanisms
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14 Terms
Hydration (basic & acidic)
Favor for ketone
Sped up by adding H+ or OH to the reaction
Acetal Formation
2 OH mol attack carbonyl
Hemiacetal intermed
TsOH & H2SO4 (expt = H3O+)
Acetal Formation + protecting group
Ald favors acetal
Eq favors reactant for ket
Imine Formation
C=N / cat.H+
Nitrile attacks H → N
Kicks H
Enamine Formation
Nitrile attacks adj H → N → kicks + charge
Wolf-Kishner Reduction
Acid Catalyzed Hydrolysis of Acetals
Acetal = Carbonyl + 2 ROH
Acid Catalyzed Hydrolysis of Imines
Imine → H2O/Cat.H+ → Carbonyl + 2 RNH2
Acid Catalyzed Hydrolysis of Enamines
Enamine → H2O/Cat.H+ → Carbonyl 2 R2NH
Red of Ald & Ket
H2 / Pd
Grignard Reagents
Cyanohydrin Hydration
Wittig Reaction (O + ket + PPh3)
convr ald & ket = alkene
Ph3P = CHR
unstable ylid = Z alkene
stable ylid = E alkene
E more stable than Z
Baeyer-Village Oxidation
prot ke w acid → tert intermed → drives eq → proton transfer
