Alkene Reactions

hydration of an alkene

reactant = alkene, H2O

reagent = acid (H3O+)

product = alkane, alcohol, markovnikov

dehydration of an alkene (synthesis)

reactant = alcohol

reagent = acid catalyst (H3O+)

product = zaitsev alkene, H2O

generally E1 reaction

hydrohalogenation: alkenes

reactant = alkene, hydrohalogen (H-X, X = Cl, Br, I)

reagent = none

product = markovnikov addition of X, enantiomers

radical hydrohalogenation: alkenes (no mechanism)

reactant = alkene, H-X

reagent = RO-OR

product = anti-markovnikov addition of X

halogenation: alkenes (addition of halogens)

reactant = alkene, X2

intermediate = halonium ion (3 membered ring)

product = alkane, ANTI addition of X2 (2nd addition on more substituted C), enantiomers

halohydrin: alkenes

reactant = alkene, X2

reagent = H2O solvent

intermediate = halonium ion (3 membered ring)

product = alkane/alcohol, ANTI addition of X and OH (H2O addition on more subsituted C), enantiomers

oxymercuration of alkene

reactant = alkene

reagent = Hg(OAc)2, NaBH4

intermediate = halonium ion (3 membered ring) —> halogenation type product

product = alkane/alcohol, ANTI addition of H and OH (OH more substituted position), HgOAc is replaced by H stereo-retentively

hydroboronation of alkenes

reactant = alkene

reagent = H3THF, H2O2, NaOH

product = 1. SYN addition of H and BH2, H goes on more subsituted C, 2. OH replaces BH2 stereo-retentivley, anti-markovnikov

catalytic hydrogenation

reactants = alkene, H2

reagent = metal (pt, pd, or ni)

product = alkane, SYN addition of H

epoxidation: alkene

reactants = alkene

reagent = McPBA

product = epoxide (3-membered ring)

ring opening epoxides: alkenes

1st form epoxide

reagent = H3O+ and H2O

product = anti diol = 2 groups on opposite plane (one wedge/one dash)

dihydroxylation: alkenes

reactants = alkene

reagent = OsO4, H2O2 or KmnO4, NaOH

product = SYN diol = 2 OH groups on the same plane (both wedge/both dash), enantiomers

ozonolysis: alkenes

1) split alkene

2) put o on split ends

3) oxidative = each H directly on alkene becomes OH, reductive = done