Organic Chemistry II Reactions

  1. Sources of R-
    • Organometallic Reagents
    • ex) Alkyllithium reagents (RLi)
    • ex) Grignard reagents (RMgBr)
    • ex) Lithium Dialklcuprates (R2CuLi)
  2. Sources of H-
    • Hydride Reagents
    • ex) Lithium Aluminum Hydride (LiAlH4)
    • ex) Sodium Borohydride (NaBH4)
  3. Step 1: The leaving group leaves in a heterolysis step yeilding a carbocation intermediate
    Step 2: A nucleophile attacks the carbocation in a coordination step
    SN1
  4. Step 1: The leaving group leaves, generating a carbocation intermediate
    Step 2: H+ is eliminated with the aid of a base to yield a double bond
    E1
  5. Ammonia → Primary Amines
    Alkylation by treatment with an alkyl halide with a good leaving group
  6. Amines → Nucleophilic amine
    Alkylation by treatment with an alkyl halide with a good leaving group
  7. Alkoxide anion (RO-) ↔ Alkyl halide (R'X)
    Williamson Ether Synthesis
  8. Opening an epoxide (3 membered ring) or oxetane (4 membered ring)
    • SN2 reaction that relieves their ring strain
    • Under neutral or basic conditions: The nucleophile attacks the less alkyl-substituted carbon of the epoxide ring
    • Under acidic conditions: the nucleophile attacks the more highly alkyl-substituted carbon of the ring
  9. Vinyl halide → alkyne
    • E2
    • With strong base (H2N)-: terminal alkyne
    • With less strong base: internal alkyne
  10. Poor amine leaving group → tetra alkyl ammonium ion
    Hofmann elimination using an excess of an alkyl hallide loke CH3Br
  11. Alkene + Proton = The most stable Carbocation intermediate
    Markovnikov's rule
  12. Alkyne → Vinyl substituted alkene
    Electrophilic addition of a bronsted acid
  13. Alkene → 1,2-dihalide
    Anti addition of Br2 or Cl2
  14. Addition of water to an alkene or alkyne
    Oxymercuration-reduction
  15. Alkene → Epoxide
    Treatment with a peroxyacid
  16. Alkene → Alcohol
    • Step 1: Addition of BH3 to the alkene to produce an alkylborane
    • Step 2: The alkylborane is converted to the Alcohol
  17. Alkyne → Enol → Ketone or Aldehyde
    Use a bulky dialkylborane like disiamylborane
Author
aokeiyi
ID
338551
Card Set
Organic Chemistry II Reactions
Description
Reaction types
Updated