Groups added to alkene addition reactions

Hydrohalogenation

HCl, HBr, HI

H and X Markovnikov (unless ROOR is present) (check for shifts)

Acid catalyzed hydration

H2SO4 H2O

(think H3O)

H and OH(Markovnikov) (check for shifts)

Oxymercuration/Demercuration

1) Hg(OAc)2, H2O(or Nuc)

2) NaBH4

H and OH (Markovnikov))

Hydroboration-Oxidation

1. BH3, THF

2. H2O2, NaOH, H2O

H and OH(anti-Markovnikov) (syn addition)

Catalytic Hydrogenation

H2 w/ Pt, Pd, Ni

H and H(syn-addition)

Halogenation

Br2 and Cl2

(add an inert solvent CH2Cl2 or CCl4)

X and X(anti-addition)

Halohydrin Formation

Br2 or Cl2 w/ H2O

X and OH (anti mark) (anti-addition)

Anti Dihydroxylation

OH and OH(anti-addition)

Syn Dihydroxylation

OsO4 (cataly.) with Na2SO3/H2O or NaHSO3/H2OORKMnO4 NaOH w/ Cold

OH and OH(syn-addition)

Oxidative cleavage

O3

DMs or Zn/ H2O

O and each double bonded carbon

Sia 2BH

H2o2 NaoH

step #1 triple to double bond, add on sia bh, sia bh become OH, then tautomerism, move double bond to O (put on less substituted side)

NaNH2

carbon group + halogen

extend carbon chain, will deprotonate and then add on carbon chain

H2

Lindlar's catalyst

Alkyne to a cis (Z) alkene

Na, NH3

alkyne to trans alkene

NaNh2, H2O

double to triple (must put equivalences)