Alkene Addition Reactions

Hydrohalogenation

(Requires a strong acid) - HCl, HBr, HI
Markovnikov
No stereochemical control (racemic mixture)
Attaches a hydrogen and a halogen

Hydrohalogenation (In Peroxide RO-OR)

(Requires Strong Acid) - HCl, HBr, HI
Anti-Markovnikov
No stereochemical control
Attaches a hydrogen and a halogen

Acid-Catalyzed Hydration

Uses H2SO4 & H2O
Markinov
No syn / Anti (Adds an alcohol and hydrogen)
Attatches an OH and H to the molecule

Hydroboration

Uses BH3 *THF or NaOH & H2O2
Anti-Markovnikov
Syn addition (Concerted reaction)
Attaches an OH to the alkenes

Hydrogenation

Uses H2 (Pd, Pt, Ni catalysts)
No Markovnikov / Anti-Markovnikov
Syn addition
Results in two hydrogens being added across alkene

Halogenation

Uses X2 (X= Cl or Br)
No Markovnikov / Anti-Markovnikov
Anti Relationship
(Uses Halonium ion intermediate (basically just two carbons bonding to the same halogen))
Results in an addition of a halogen on both sides across an alkene

Hydroxyhalogenation

Uses Water and X (X= Cl or Br)
OH bond goes to more substituted carbon
Anti Relationship
Results in an OH and Halogen to be added across an alkene (can form enantiomers)

Epoxidation

Uses mCPBA
Syn Relationship
Dead giveaway is that there are a lot of oxygens attached to an group
Uses a mechanism with 4 arrows in a concerted reaction
Results in two products
(Carboxylic acid & an Epoxide)

Dihydroxylation (syn selective)

Uses OsO4
Syn relationship
No Markinov / Anti-Markovnikov
Results in a molecule with an OH added to both sides across an alkene

Dihydroxylation (anti selective)

Two steps,
First step uses mcPBA
Second step uses an OH (which opens up epoxide) and Water
Anti Relationshio
No Markovnikov / Anti-Markovnikov
Results in an an OH an being attatched across the alkene

Ozonolysis

Two step reduction
First step uses ozone to lyse (cut) a double bond
Second Step uses DMS (or ZN & H2O)
Basically turns carbons into carbonyls
Results in two separate molecules, split across the original alkene, both double bonded to an Oxygen where there was originally a double bond