Addition of HCl, HBr, and HI

HX

-------------->

Ether

void - markovnikov

H and X

Addition of halogens Cl₂ and Br₂

X₂

-------------->

CH₂Cl₂

trans

X and X

Halohydrin formation

X₂

-------------->

H₂O

trans - markovnikov

X and OH, and HX

Addition of water by oxymercuration-demercuration

1. Hg(OAc)₂, H₂O/THF

------------------------->

2. NaBH₄

 void - markovnikov

OH and H

Addition of water by hydroboration-oxidation

1. BH₃, THF

------------------------->

2. H₂O₂, OH^-

cis - nonmarkovnikov

H and OH

Catalytic hydrogenation

H₂

------------------------->

Pd/C or PtO₂

cis

H and H

Reaction with ozone followed by zinc in acetic acid

1. O₃

------------------->

2. Zn / H₃O

cleavage, C=O for both carbons

Reaction with KMnO₄

KMnO₄, H₃O

---------------------->

cleavage, C=O at cut point for both carbons. Previous H are replaced by OH. If both substituents of C are H, CO₂ is produced