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1.82
50 Y
2
sp -S 1.75
55
-0 TR sp-S
C=Ssp-S
1.68
1.67
SI
49 IS
C
Carbanion stability
Vinyl > phenyl > Cyclopropyl > ethyl > n-propyl > isobutyl > neopentyl >cyclobutyl > cyclopentyl
Reducing Agent
Reagent Preferred Solvents Functions Reduced
Sodium Borohydride ethanol; aqueous ethanol aldehydes to 1°-alcohols
NaBH4 15% NaOH; diglyme ketones to 2°-alcohols
avoid strong acids 1,2-reduction of enones is favored by
CeCl3inert to most other functions
Lithium Aluminum ether; THF aldehydes to 1°-alcohols,ketones to 2°-
Hydride (LAH) avoid alcohols and amines alcohols.carboxylic acids to 1°-alcohols
LiAlH4 avoid halogenated esters to alcohols,epoxides to alcohols
compounds nitriles & amides to amines
avoid strong acids halides & tosylates to alkanes
most functions react
Lithium tri t- ether; THF fast:-acid chlorides to aldehydes
Butoxyaluminohydride avoid alcohols and (at -78° C),3°-amides to aldehydes (at -78°
LiAlH(Ot-C4H9)3 amines,avoid halogenated C),nitriles to aldehydes (at -78° C)
50 Y
Mg or Al or Zn or Fe cleaves activated substituents
water, alcohols, acetic acid nitro groups to amines
55
-0 TR
or aqueous mineral acid C=O (aldehyde/ketone) to CH2
SI
Oxidising Agent
49 IS
Reagent Preferred Solvents Functions Oxidized
Jones Reagent aqueous sulfuric acid & acetone 1°-alcohols to carboxylic acids
H2CrO4 (avoid acid sensitive systems) aldehydes to carboxylic acids
2°-alcohols to ketones
avoid amines and sufides
Collins Reagent methylene chloride 1°-alcohols to aldehydes
CrO3 • 2 C5H5N (CH2Cl2) 2°-alcohols to ketones
C