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NaNH2
double dehydrohalogenation, terminal alkyne
KOH
double dehydrohalogenation, internal alkyne
NaNH3
alkyne -> trans alkene
Lindlar’s catalyst
alkyne -> cis alkene
HgSO4/H2SO4
triple -> double, Mark add H and OH, ketone
1 eq. X
cis/trans alkenes
2 eq. X
tetrahalides
Hg2+ catalyzed hydration
Mark add H2O -> enol -> ketone
Sia2BH
hydroboration
H2O2/NaOH
anti-Mark hydration -> enol -> ketone
KMnO4/O3
oxidative cleavage
H2/Pd, Pt, Ni
alkane
enol
OH-C=C
aldehyde
RH>C=O
ketone
RR>C=O