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HX
Two Step
Electrophilic addition of a proton from the hydrogen halide (forms carbocation).
2. Halide ion (X-) attacks carbocation.

H2O, H2SO4
Three Step
1. Electrophilic addition (forms carbocation).
2. Neutral water nucleophilically attacks the carbocation intermediate.
3. Protonated alcohol intermediate is deprotonated by water in solution.

ROH (CH3OH)
Three Step
1. Electrophilic addition of a proton from the protonated alcohol (forms carbocation).
2. Neutral alcohol nucleophilically attacks the carbocation intermediate.
3. Protonated ether intermediate is deprotonated by alcohol in solution.

X2
1. Electrophilic addition of a halogen atom – forms a bridged halonium intermediate.
2. Halide ion (X-) attacks the more substituted carbon of the bridged halonium intermediate.

X2 in H2O
1. Electrophilic addition of a halogen atom – forms a bridged halonium intermediate.
2. Water attacks the more substituted carbon of the bridged halonium intermediate.
3. Protonated alcohol intermediate is deprotonated by water in solution.

H2
Single step
Epoxidation
Single step (concerted)
Hydroboration oxidation rxn
Single step (concerted)