Alkene Reactions

For electrophilic additions to alkenes, the electrophile adds in a way so that the most stable carbocation is formed.

• Addition of halides
• 
• Markovnikov's rule applies

• Addition of water
• 
• Markovnikov's rule applies
• (Strong acids ex: H₂SO₄)

• Like hydration reaction, but instead of water, it reacts with an alcohol (methanol, ethanol, etc.)
• Occurs in strong acids like H₂SO₄

• Uses Br₂ and Cl₂ (F₂ too violent, I₂ products too unstable)
• 
• Inert non-polar solvent (ex: CCl₄)
• Anti addition
• Stereospecific reaction
• Regeoselective (nuc attacks more substituted carbon)
• Markovnikov's rule applies

• Like regular electrophilic addition, except X⁺ is opened by a different nucleophile.
• 
• In water or alcohols
• Anti addition
• Stereospecific reaction
• Regeoselective (nuc attacks more substituted carbon)
• Markovnikov's rule applies

• Solvents: Hg(OAc)₂, THF, H₂O
• 
• Electrophilic addition of ⁺Hg(OAc)
• Anti addition
• Stereospecific
• Regeoselective (nuc attacks more substituted carbon)
• Markovnikov's rule applies
• Demurcuration (removes ⁺Hg(OAc) using NaBH₄)

• Tetrahydrofuran
• 

• Uses: BH₃, ^-OH, H₂O₂, H₂O
• 1)BH₃ syn addition (same side)
• 
• 2)Oxidation (^-OH, H₂O₂, H₂O)
• 
• Anti-Markovnikov alcohol product produced
• Sterospecific

• Initiation:
• 
• Propagation:
• 
• Termination: Combo of any two radicals
• Addition of HBr in H₂O₂
• Free radical mechanism
• Anti-Markovnikov

• \
• Solvent can be alcohol or carboxylic acid
• Stereospecific: Syn addition

• 
• Concerted reaction
• Syn addition

• 
• Anti addition of O's

• m-chloroperoxybenzoic acid
• 

• 
• Aldehydes can be oxidized to carboxylic acids
• =CH₂ oxidized to CO₂ + H₂O
• 

• 
• Products are ketones and aldehydes
• =CH₂ oxidized to H₂C=O

H₂C=CH₂

H₂C=CH-CH₃