-
LiAlH4 reduces...
everything except alkenes & alkynes -> alcohol
-
DIBALH reduces...
everything except alkenes & alkynes -> aldehyde
-
NaBH4 reduces...
ketones and aldehydes -> alcohol
-
H2, Pd catalyst reduces...
alkenes, alkynes, aldehydes & ketones
-
H2, Raney Ni reduces...
alkenes, alkynes, thiols to alkanes
-
N2H4, KOH, H2O, heat reduces...
ketones/aldehydes
(Wolff-Kishner)
-
Zn(Hg), HCl, heat reduces...
ketones & aldehydes ->alkanes
(Clemmensen)
-
Na metal, liq NH3, -33oC reduces...
alkynes -> trans-alkenes
-
Sn, HCl reduces...
nitro groups -> amines
-
-
-
-
RCOOR' + LiAlH4 ->
RCH2OH
-
-
RCONH2 + LiAlH4 ->
RCH2NH2
-
-
-
RCOCl + LiAlH[OC(CH3)3]3 ->
RCHO
-
-
RCHO + H2, Pd cat ->
RCH2OH
-
unknown is soluble in water
low MW compound (<4-6C)
-
unknown is soluble in 2.5M NaOH
organic acid (carboxylic acid or phenol)
-
unknown is soluble in 0.6 NaHCO3
carboxylic acid
-
unknown is soluble in 1.5M HCl
amine
-
unknown is soluble in conc. H2SO4
NOT a halide
-
Solubility test progression
- 1) Water
- 2) NaOH
- 3) NaHCO3
- 4) HCl
- 5) H2SO4
-
chromic acid oxidation test
alcohols, aldehydes, ketones
-
iodoform/haloform test
alcohols, methyl ketones
-
Lucas test
H2O soluble alcohols
-
2,4-DNP test
aldehydes, ketones
-
-
-
KMnO4 oxidation
alkenes
*strong oxidizer - also ROH's & aldehydes
-
-
Friedel-Crafts alkylation
non-electron-poor aromatics
-
hydroxamic acid test
ester
-
ester hydrolysis test
ester
-
NaI test
SN2 alkyl halide test
-
AgNO3 test
SN1 alkyl halide test
-
dinitrobenzoate derivative
alcohol
-
naphthylurethane derivative
alcohol
-
phenylurethane derivative
alcohol
-
2,4-DNP derivative
aldehyde/ketone
-
semicarbazone derivative
aldehyde/ketone
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