Halogenation
X2 or NBS (Br2)
Anti-addition
forms carbocation
Halohydrin
X2, H2O
trans-enantiomers
Anti-Marvkov (OH on more sub C)
Alkynes: halide ketone
Hydroboration/ Oxidation
1. BH3/ 9-BBN, 2. H2O2, NaOH
Anti-Markovnikov
(least sub C)
Alkynes: Aldehyde
Hydration
H2SO4/ TsOH, H2O
Markovnikov (add an OH to most sub C)
same as hydrohalogenation
Alkynes: H2SO4, HgSO4, H2O
ketone
Hydrohalogenation
H-X
same as hydration
Acytylide
Three bond anion
Attacks carbon and replaces halogen
NaH
NaNH2
deprotonates H
forms triple bond anion
2 equiv H-X
Genimal addition
SoCl2, pyridine
alcohol --> halide
Epoxide and H2O work up
add 3 carbons with OH at middle carbon
triple bond anion with water
anti addition of OH and aldehyde