Alkene Addition Reactions

Hydrohalogenation (HBr, HCl, HI)

Markovnikov addition of H and Br/I/Cl on each side of double bond

Look out for hydride shift

Cl to the more sub., H to the less sub. (more H)

Hydrohalogenation (HBr with ROOR)

Addition of H and Br on each side

Anti-markovnikov

Br on the side w less sub. (more H), H on the side with more sub.

Dihydroxylation (Dilute and HX)

1. Double bond attacks H in the solvent

2. hydride/methyl shift

3. when OH is final product:

- H3O being attacked ->forms H2O

- H2O attaches to + carbon

- H2O comes back to take away an H from the attached H2O

oxymercuration Hg(OAc)2, H2O NaBH4

- Normally: attaches one planar OH on the side with more sub.

- When H2O is changed: attach whatever the thing is - H

Markovnikov and Anti

hydroboration BH3, THF, NaOH, H2O

BH3, THF, NaOH, H2O

One OH but with in or out of page + En

Anti-mark and syn

Hydrogenation H2

syn: both has wedges or dashes

Halohydrin (Br2, H2O)

Halides adds to less sub

OH adds to more sub

Anti- addition

Epoxidation (mCPBA/RCO3H)

Anti addition

OH on each side

draw formation when chiral

OsO4 or KMnO4

syn addition

two OH on each side

draw formation when chiral

O3 Oxidative Cleavage

Cut double bond in half and add O on each side