|
alkyl halide + base
|
alkene
|
|
|
alkene + HX
|
alkyl halide
|
|
|
alkene + X2
|
dihalide
|
|
|
alkene + X2/H2O
|
halohydrin
|
|
|
alkene + H2; Pd/c
|
alkane
|
|
|
alkene + HBR; light, heat
|
alkyl halide
|
|
|
alkene + ozone
|
aldehydes / ketones
|
|
|
dihalide + strong base
|
alkyne
|
|
|
alkene + X2 + base
|
alkyne
|
|
|
acetylene + NaNH2 + RX
|
alkyne
|
|
|
alkyne + X2
|
dihaloalkene
|
|
|
alkyne + HgSO4, H2O; H+, H2SO4
|
ketone
|
|
|
acetylene + HgSO4, H20; H+, H2SO4
|
aldehyde
|
|
|
alkyne + HX
|
alkenyl halide
|
|
|
alkyne + Lindlar
|
cis-alkene
|
|
|
alkyne + alkali metal
|
trans-alkene
|
|
|
alkyne + NaNH2 + RX
|
alkyne
|
|
|
alkene + Hg(OAc2), H20; NaBH4, OH-
|
alcohol
|
|
|
alkene + H3PO4, H20
|
alcohol
|
|
|
alkene + BH3, THF; H2O2
|
alcohol
|
|
|
alkene + OSO4
|
diol
|
|
|
alkene + KMnO4
|
diol
|
|
|
aldehyde + NaBH4
|
primary alcohol
|
|
|
ketone + NaBH4
|
secondary alcohol
|
|
|
carbonyl + Grignard
|
alcohol
|
|
|
ester + LiAlH4
|
primary alcohol
|
|
|
carboxylic acid + LiAlH4
|
primary alcohol
|
|
|
acid chloride + LiAlH4
|
primary alcohol
|
|
|
anhydride + LiAlH4
|
primary alcohol
|
|
|
tertiary alcohol + HX
|
alkyl halide
|
|
|
primary alcohol + PBr3
|
primary alkyl bromide
|
|
|
primary alcohol + SOCl2
|
primary alkyl chloride
|
|
|
secondary alcohol + SOCl2
|
secondary alkyl chloride
|
|
|
secondary alcohol + PBr3
|
secondary alkyl bromide
|
|
|
primary alcohol + PCC
|
aldehyde
|
|
|
secondary alcohol + Na2Cr2O7
|
ketone
|
|
|
primary alcohol + Na2Cr2O7
|
carboxylic acid
|
|
|
secondary alcohol + PCC
|
ketone
|
|
|
ester + DIBAH
|
aldehyde
|
|
|
aldehyde + Jone's
|
carboxylic acid
|
|
|
aldehyde + HCN
|
cyanohydrin
|
|
|
cyanohydrin + H2SO4/H20
|
carboxylic acid
|
|
|
ketone + primary amine
|
imine
|
|
|
ketone + secondary amine
|
enamine
|
|
|
ketone + Zn(Hg), HCl
|
alkane
|
|
|
primary alcohol + Jones'
|
carboxylic acid
|
|
|
secondary alcohol + Jones'
|
ketone
|
|
|
ketone + LiAlH4
|
secondary alcohol
|
|
|
nitro group + LiAlH4
|
NH2
|
|
|
aldehyde + LiAlH4
|
primary alcohol
|
|
