Reductions

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Reduction Overview.png

General Guidelines for Various Reducing Agents
Hydride Donor	Iminium Ion	Acid Halide	Aldehyde	Ester	Amide	Carboxylic Salt
LiAlH₄	Amine	Alcohol	Alcohol	Alcohol	Amine	Alcohol
DIBAL-H	–	Alcohol	Alcohol	Alcohol Aldehyde	Amine Aldehyde	Alcohol
NaAlH(Ot-Bu)₃ (Red-Al)	–	Aldehyde	Alcohol	Alcohol (slow)	Amine (slow)	–
AlH₃	–	Alcohol	Alcohol	Alcohol	Amine	Alcohol
NaBH₄	Amine	–	Alcohol	–*	–	–
NaCNBH₃	Amine	–	Alcohol (slow)	–	–	–
Na(OAc)₃BH	Amine	–	Alcohol (slow)	Alcohol (slow)	Amine (slow)	–
B₂H₆	–	Alcohol	Alcohol	Alcohol (slow)	Amine (slow)	Alcohol
Li(Et)₃BH (Super Hydride)	–	Alcohol	Alcohol	Alcohol	Amine	–

* α-alkoxy esters are reduced to the corresponding alcohol