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NaBH4 (for aldehyde/ketone), LiAlH4 (stronger)
Reduces C=O to OH
forms OH
wittig reagent
Ph3P=Ch2
Wittig Reagent (Ph3P=CR2)
Converts C=O to C=C
C=C formed
HCN (base catalyzed)
cyanohyrdin formation
adds -CN to carbonyl carbon
1° or 2° amine, acid catalyzed
Nucleophilic addition to C=O, forms C=N or enamine
Imine or enamine
primary amine forms imine
secondary amine forms enamine
imine vs enamine