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Alkene + HBr
Br on most
Alkene + H2, Pd/C
add Hs syn
Alkene + 1. O3 2. H2O
split bond, two double Os
Alkene + Br2, H2O
OH on most, BR on least, anti
Alkene + Br2
Br add anti
Alkene + mCPBA
epoxide
Alkene + 1. BH3 2. NaOH, H2O2, H2O
OH on least
Alkene + H2O cat. H2SO4
OH on most
Alkene + CH3OH cat. H2SO4
OCH3 on most
Alkene + HBr, peroxide
Br on least
Alkene + 1. Na+ 2. alkyne
Alkyne
Ether + HBr (equiv.)
Alcohol and Alkyl Halide
Ether + HBr (excess)
2 alkyl halides
Alkyne + 1. BH3 2. NaOH, H2O2, H2O
Aldehyde
Alkyne + H2O cat. H2SO4
Ketone
Alkyne + 1. NaNH2 2. CH3CH2Br
deprotonate and add C chain
Alkyne + H2 Pd/C
Alkane
Alkyne + H2 Lindlar
cis Alkene
Alkyne + NaNH3
trans Alkene
Alkane + Br2 hv
Br on most
Alcohol + H2SO4 hv
Alkene
Alcohol + HBr
Br substitution
Alcohol + PBr3 pyrimidine
Br substitution flip stereochemistry
Alcohol + 1. NaH 2. Ch3Br
Ether
Epoxide + 1. NaOCH3 2. H3O+
OH most OCH3 least
Epoxide + H2O cat. H2SO4
OH on least
Alkyl Halide + 1. MgBr 2. Ether 3. H3O+
Alcohol
CH3CH2MgBr + 1. Ether 2. H3O+
Alcohol
Epoxide + 1. CH3CH2MgBr 2. H3O+
Alcohol R group added
Alkyl Halide + Br2 hv
Br on most (replaces an H)
Alkene + HBr peroxide
Br on least
Alkene + NBS hv
Alkene (Br replaces an H)