Chem 124

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Chem 124
2013-04-22 00:50:15
Ethers Aldehydes Ketones

Ethers, Aldehydes and Ketones (coming soon)
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  1. How do you make an Ether?
    • A. 1)Hg(OAc)2,R-OH 2)NaBH4 
    • B. Williamson Ether Synthesis
  2. What must the starting material be for Williamson Ether Synthesis?
    A primary (best) or secondary alcohol
  3. What kind of alkyl halide is required in a Williamson Ether Synthesis?
    A 1° alkyl halide
  4. What are the rules of Ether rxns?
    • A. If the starting ether has only 1° or 2° carbons  the halide will do SN2 to the less substituted carbon
    • B. If the starting ether has 3° carbon the halide will do SN1 to the most substituted carbon
  5. How does the Oxymercuration make the ether?
    It adds the R-OH to the most substituted carbon and then the NaBH4 takes the H off the alcohol to make the ether.
  6. What does PBr3 do?
    It kicks off an alcohol
  7. What adds 2 OH groups to an alkene?
    OsO4 and NaHSO3
  8. What does NaBH4 do?
    It reacts with carbonyls except for Carboxylic acids and Esters, to make an alcohol
  9. What does PCC do to a primary alcohol?
    It turns it into an aldehyde
  10. What does ozonolysis (O3, DMS) do?
    Make 2 carbonyl groups on both sides of an alkene after breaking it.
  11. How do you make a ketone from a 2° alcohol?
    • A. CrO3, heat and acetone (aq)
    • B. Na2Cr2O7, H2SO4 and H2O
  12. How do you turn a carbonyl into an alcohol?
    • A. 1)LiAlH2)H2O
    • B. NaBH4, MeOH or H2O
  13. What does Ph3PR do?
    It replaces the carbonyl with an alkene and the R group
  14. What does CrO3 H2SO4 do to a 1° alcohol
    Turns it into a carboxylic acid
  15. What does POCl3 do?
    Turns a 2° alcohol to an alkene to the least sub carbon
  16. How do you turn a carbonyl into an acetal? How do you turn it back?
    • A. H+, 2ROH
    • B. H+, H2O
  17. Mechanism for forming acetal
  18. How do you get rid of a carbonyl?
    • 1) H+, H2NNH2
    • 2) KOH, H2O (100-200°C)
  19. How do you turn an alkyne to an aldehyde?
    • 1) BH3
    • 2)H2O2,NaOH
  20. How do you turn an alkyne into a ketone?
    HgSO4, H2SO4
  21. How do you turn an ester into a carboxylic acid?
    H+, H2O