Organic Chemistry Reactions

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Organic Chemistry Reactions
2013-07-30 18:43:03
alkanes alkenes alkynes addition reduction oxidation

Synthesis cleavage reduction and oxidation for alkanes, alkenes, and alkynes.
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  1. Catalytic Hydrogenation (Alkene)
    add H2 and a metal catalyst to a double bond to form syn addition
  2. Addition of HX (Alkene)
    The double bond acts as a lewis acid to react with the HX. The proton adds to the least substituted carbon if the alkene is asymmetrical
  3. Addition of X2 (Alkene)
    The double bond acts as a nucleophile and attacks an X2 (diatomic halogen) molecule forming a cyclic halonium ion which is attacked by the resulting free radical and attaches through anti-addition
  4. Addition of H20 (alkene)
    the double bond is protonated under acidic conditions then the carbocation reacts with water
  5. Free radical addition (alkene)
    Disobey Markovnikov's rules because the free radical add to the double bond
  6. Hydroboration (Alkene)
    the boron atom attaches to the double bond then an oxidation hydrolysis with an aqueous base produces an anti-markovnikov alcohol
  7. Oxidation (Alkene) with cold KMnO4
    potassium permanganate produces syn addition 1,2-diol which is glycol
  8. Oxidation (Alkene) with hot acidic KMnO4
    Potassium permanganate cleaves terminal double bonds to form a carboxylic acid and CO2. Nonterminal double bonds are split to form 2 carboxylic acids
  9. Ozonolysis (Alkene)
    Treatment with ozone (O3) followed by reduction with Zinc and Water makes 2 Aldehydes. If sodium borohydride (NaBH4) is added the product will be 2 corresponding alcohols
  10. Peroxycarboxylic Acids (Alkene)
    Peroxyacetic acid (CH3CO3H) and m-chloroperoxybenzoic acid (MCPBA) form oxiranes which are epoxides
  11. Polymerization (Alkene)
    a radical under immense heat and pressure form a long chain polymer from ethylene
  12. Reduction (Alkyne)
    Palladium and barium sulfate (Lindlar's Catalyst) hydrogenate the triple bond and then Quinoline immediately stop the process after adding only 1 H2 to form a double bond or sodium and Liquid ammonia (NH3) are used as a free radical mechanism.
  13. Electrophilic addition (Alkyne)
    occurs through Markovnikov's rule
  14. Free radical addition (Alkyne)
    The free radical does not adhere to Markovnikov's rule and attacks the triple bond the same as with an alkene
  15. Hydroboration (Alkyne)
    The boron acts as a lewis acid and attaches to the less stericaly hindered carbon then through oxidation hydrolysis with peroxide the boron and its substituents are cleaved
  16. Oxidation (Alkyne) with KMnO4
    The triple bond is cleaved to form 2 carboxylic acids
  17. Oxidation (Alkynes) with O3
    the triple bond is cleaved to form 2 carboxylic acids