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Reaction pathways
Polar aprotic solvent
SN2 with HydroxideSN2 / DMSO, DMF, or acetone
SN2 with CyanideSN2 / DMSO or DMF
SN1 SolvolysisSN1 / Water or aqueous ethanol
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63Reagents
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Reagent functions
Mild reduction of aldehydes and ketones to alcohols
Sodium BorohydrideDoes NOT reduce esters, amides, carboxylic acids, or C=C bonds. Works in protic solvents (MeOH, EtOH).
Lithium Aluminum HydrideVery reactive! Violently reacts with water. Use anhydrous ether or THF. Quench carefully with water.
DIBAL-HTemperature critical! At -78°C stops at aldehyde. Warmer or excess gives alcohol.
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Functional groups
Saturated hydrocarbons with only C-C single bonds. Least reactive functional group.
AlkaneHydrocarbons
AlkeneHydrocarbons
AlkyneHydrocarbons
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