alkene reactions

hydrohalogenation reagents

Hydrogen and a halogen -

HBr, HCl, etc (markovnikov)

HBr/ROOR (anti-markovnikov)

Hydrohalogenation mechanism

• regioselectivity

Hydration reagents

H3O+, [H+]/H2O, [H2SO4] (markovnikov)

1)BH3 THF/H2O2, NaOH (anti markovnikov)

Hydration - acid catalyzed reaction

• H+]/H2O, [H2SO4]

• markovnikov position

• can be rearrangements

Hydration - oxymercuration/demercuration reaction

1) 𝐻𝑔(𝑂𝐴𝑐)2, THF, H2O/ NaBH4

• markovnikov position

• no rearrangements

Hydration - hydroboration/oxidation

• forms double bond on anti-markovnikov position

• syn products if 2 chiral centers

catalytic hydrogenation (dont need to know mechanism)

• adds H/H across double bond

• syn products if 2 chiral centers

Halogenation

• forms bridge intermediate

• forms anti products with chiral centers

Halogenation reagents

di-halogens

ex) Br2

halohydrin formation reagents

di halogens + water

ex? Br2/H2O

halohydrin formation mechanism

• OH group on more substituted carbon

Anti-dihydroxylation reagents

1) RCO3H / 2H3O+

anti-dihydroxylation (dont need to know mechanism)

anti products if chiral centers

syn-dihydroxylation reagents

OSO4 / NMO

OSO4 / NaHSO3, H2O

KMNO4, NaOH / cold

syn-dihydroxylation (dont need to know mechanism)

• forms syn products

Oxidative cleavage reagent

O3 / DMS

Oxidative cleavage mechanism