Organic Chemistry

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Organic Chemistry
2010-05-04 15:37:49
chapter organic chemistry II

Exam 3 Organic chemistry II
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  1. LiAlH4
    • Very powerful reducing agent. Aldehydes are reduced very easily.
    • When a carboxylic acid is treated with this it is reduced to 1o Alcohol
  2. Acyl chlorides can be reduced to aldehydes by...
    Acyl chloride
    treating them with LiAlH [OC(CH3)3]3, lithium tri-tert-butoxyaluminum hydride, at -78°C.
  3. Carboxylic acids can be converted to acyl chlorides by...
    Using SOCl2
  4. Reducing agents
    • Ni/H2
    • Pd/H2
    • NaBH4 Sodium borohydride
    • Grignard Reagent Mg/ diethyl ether
  5. 1o Alcohol ---------->Aldehyde
    PCC (C5H5NH+CrO3Cl-)
  6. Aldehydes by Reduction of Acyl Chlorides, Esters, and Nitriles
    When any aldehyde is treated with LiAlH4 It is reduced all the way to 1o alcohol
  7. Two derivatives of aluminum hydride that are less reactive than LAH (in part because they are much more sterically hindered and, therefore, have difficulty in transferring hydride ions) are:
    Lithium tri-tert-butoxyaluminum hydride and diisobutylaluminum hydride (DIBAL-H)

  8. Acul chrolide -----> aldehyde
    ester -----> Aldehyde
    Nitrile -----> aldehyde
  9. Acyl group
  10. What type of molecule is ethyl formate?
  11. Reduction of an Acyl Chloride to an Aldehyde
  12. Reduction of an Ester to an Aldehyde
  13. Reduction of a Nitrile to an Aldehyde
  14. synthesize propanal from each of the following:(a) 1-propanol (CH3CH2CH2OH) (b) propanoic acid (CH3CH2CO2H)
    • (a) CH3CH2CH2OH + PCC-----> CH3CH2CHO
    • (b) CH3CH2COHO --SOCl2--> CH3CClO [---(1)LiAlH(o-t-Bu)3 -78℃(2)H2O-->] CH3CH2CHO
  15. Treating a nitrile (R—CN) with either a Grignard reagent or an organolithium reagent followed by hydrolysis yields a...
  16. KMnO4
    KMnO4 is an oxidizing agent. It will oxidatively cleave the alkene to give an aldehyde, which further oxidizes to the carboxylic acid. If it were a ketone, however, it would not further oxidize.

    Removes CH3 adds an aldehyde (adds double bond to O and an OH group)
  17. SOCl2
    removes OH adds a Cl
  18. LiAlH(OCCH3)3
    Removes halogen adds a H
  19. Functional groups
  20. More functional groups
  21. Difference between LiAlH4 and (CH3)2 Cu Li is...
    • Li Al adds a H
    • Cu Li adds a methyl group
  22. DIBAL-H
    Reduces Esters into aldehydes

    O-R into H
  23. (CH3)2 CuLi
    Removes halogen adds methyl group becoming a ketone
  24. Hg2+/H2O
    Removes triple bond and insert a ketone (Remember that number of carbons stays the same) Always count the carbons.
  25. Imine formation
  26. Imine formation—reaction with a primary amine
  27. Oxime formation—reaction with hydroxylamine
  28. Enamine Formation
  29. Amine reactions
  30. Cyanohydrin formation
  31. Wittig reaction
    Overall result is of this synthesis is:
  32. Horner–Wadsworth–Emmons modification
  33. Oxidation of aldehydes