Alkene Reaction Mastery Challenge

Catalytic Hydrogenation

• Reagents & Solvents

• Overall Mode of Addition

• Functional Group Produced

• H₂,

• Transition Metal Catalyst (Pd/CPtO₂/Ni)

• Syn

• Form Alkane

Halogenation

• Reagents & Solvents

• Overall Mode of Addition

• Functional Group Produced

• Cl₂ or Br₂ with, non-nucleophilic solvent (CH₂Cl₂)

• Anti Addition

• Dihalides

Halohydrin Formation

• Reagents & Solvents

• Overall Mode of Addition

• Functional Group Produced

• Cl₂ or Br₂ with, H20

• Anti Addition, Markovnikov, OH attaches to the more substituted carbon

• Halohydrin

Acid-Catalyzed Hydration

• Reagents & Solvents

• Overall Mode of Addition

• Functional Group Produced

• H₂SO₄ or H₃O⁺ in H₂0

• carbocation, Markovnikov, rearrangements

• Alcohol

Oxymercuration-Reduction

• Reagents & Solvents

• Overall Mode of Addition

• Functional Group Produced

• Hg(OAc)2, H20 | NaBH4, NaOH

• Anti addition, Markovnikov, no rearrangements, regioselectivity

• Alcohol

Hydroboration-Oxidation

• Reagents & Solvents

• Overall Mode of Addition

• Functional Group Produced

• BH3 * THF (or 9-BBN) | H2O2, NaOH

• Syn, Anti-Markovnikov regioselectivity

• Alcohol

Epoxidation

• Reagents & Solvents

• Overall Mode of Addition

• Functional Group Produced

• A peroxyacid (mCPBA or RCO3H

• Syn addition (concerted stereospecific addition preserving cis/trans geometry); stereospecific

Dihydroxylation (Anti)

• Reagents & Solvents

• Overall Mode of Addition

• Functional Group Produced

• RCO3H | H3O+

• Anti addition

Dihydroxylation (Syn)

• Reagents & Solvents

• Overall Mode of Addition

• Functional Group Produced

• OsO4 with NMO or KMnO4, OH-

• Syn

Oxidative Cleavage (Ozonolysis)

• O3

  • a. NaBH₄ (full reduce) = alcohols

  • b. DMS (neutral reducen) =ketones and aldehydes

  • c. H₂O₂ (oxidize) = ketones and carboxylic acids

Hydrohalogenation

HX

random, stereo, stepwise

Carbocation, rearrangement

Mark Alkyl