DAT alkene reactions

hydrohalogenation

hydrohalogenation reactants and reagents

reactants:

• alkene

reagents:

• halide bonded to H

hydrohalogenation products

markovnikov addition of a hydrogen halide across a carbon-carbon double bond. Due to a carboncation intermediate, carbon rearrangement is possible

radical addition(antimarkovnikov hyrdrohalogenation)

radical addition reactants and reagents

reactants:

• alkene

reagents:

• halide bonded to H

• ROOR

radical addition products

anti- markovnikov addition of a hydrogen halide across a carbon-carbon double bond.

acid catalyzed hydration

acid catalyzed hydration reactants and reagents

reactants:

• alkene

reagents:

• H2O or alcohol

• catalytic acid

acid catalyzed hydration products

an alkene is replaced by the markovnikov addition of H and OH(now alkane)

oxymercuration-demurcuration

oxymercuration-demurcuration reactants and reagents

reactants:

• alkene

reagents:

• 1. Hg(OAc)₂, H₂O, THF

• 2. NaBH₄

oxymercuration-demurcuration products

converts and alkene to a markovnikc alcohol without the possibility of carbocation rearramgements. stereorandom products

what is special about oxymercuration-demurcuration?

it is used to convert an alkene into an alcohol without the possibility of carbocation rearrangements

hydroboration-oxidation

markovnikov hydroboration-oxidation reactants and reagents

reactants:

• alkene

reagents:

• 1. BH₃, THF

• 2. H₂O₂, NaOH

hydroboration-oxidation products

anti-markovnikov addition of a H and OH across the carbons of the alkene

dihalogenation

dihalogenation reactantants and reagents

reactants:

• alkene

reagents:

• X₂(Br₂ or Cl₂)

• neutral, non-nucleophilic solvent(CCl₄₎

dihalogenation products

an alkane with a stereospecific anti-addition of two halides

vicinal dihalide

contains two halogen atoms bonded to neighboring carbons

halohydrin formation

halohydrin mechanism reactants and reagents

reactants:

• alkene

reagents:

• dihalide

• water molecule

halohydrin mechanism products

an alkane with a the anti-additon of a halogen and then hydroxyl group(OH) on an adjacent, more substituted carbon.

epoxidation

epoxidation reactant and reagents

reactants:

• alkene

reagents:

• RCO₃H( commonly mCPBA)

epoxidation products

an epoxide forms on either face of the alkene(now alkane). If the product is chiral, both enantiomers will be formed.

epoxide

a three memebred ring consisting of oxygen and two carbon atoms

anti dihydroxylation

anti dihydroxylation reactant and reagents

reactants:

• alkene

reagents:

• 1. RCO₃H( commonly mCPBA)

  • ex. CH₃CO₃H

• 2. H₃O+

anti dihydroxylation products

first forms and epoxide, and then a vicinal diol with two hydroxyl groups ortiented anti to one another + EN

syn dihydroxylation

syn dihydroxylation reactants and reagents

reactants:

• alkene

reagents:

• 1. OsO₄

• 2. H₂O₂

OR

• 1. KMnO_4,NaOH/ H₂O, H₂O₂

• cold

syn dihydroxylation products

a vicinal diol(with two hydroxyl groups on neighboring carbons). The two hydroxyl groups attach in the syn fashion

reductive ozonolysis

reductive ozonolysis reactants and reagents

reactants:

• alkene

reagents:

• 1. O₃

• 2. DMS or Zn, HOAc

reductive ozonolysis products

ketones and aldehydes

oxidative ozonolysis

oxidative ozonolysis reactants and reagents

reactants:

• alkene

reagents:

• 1. O₃

• 2. H₂O₂

oxidative ozonolysis products

ketones and carboxylic acid

catalytic hydrogenation

alkene reacts with hydrogen atoms on the surface of a solid metal catalyst and the alkene is reduced to an alkane

catalytic hydrogenation reactants and reagents

reactant:

• alkene

reagent:

• H₂

• a metal catalysts such as Pd, Pd/C, or Pt