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Addition of HX
Mark
Addition of HX
Anti-mark
Addition of X2
trans-addition
Halohydrin formation
trans-addition
Acid-catalysed hydration
mark, rearrangement possible
Acid-catalysed hydration
mark, rearrangement possible
Oxymerc-demerc
mark, no rearrangement
Oxymerc-demerc
mark, no rearrangement
Hydroboration
anti-mark, cis addition
Hydroboration
anti-mark, cis addition
Hydrogenation
Hydrogenation
Epoxidation
Epoxidation: RCO3H
Epoxidation: MCPBA
Syn-hydroxylation
cis-1,2-diol formed
Syn-hydroxylation
cis-1,2-diol formed
Anti-hydroxylation
trans-1,2-diol
Ozonolysis (cleavage)
Ozonolysis (cleavage)
Ozonolysis (cleavage)
Ozonolysis (cleavage)
KMnO4 cleavage
acid/neutral
KMnO4 cleavage
acid/neutral
Carbene
mark
H+ adds to C with more H
mark
X adds to C with less H
anti-mark
H+ adds to C with less H
anti-mark
X adds to C with more H