Organic Chemistry

  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...
    Image Upload 1Acyl 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)

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  8. Acul chrolide -----> aldehyde
    ester -----> Aldehyde
    Nitrile -----> aldehyde
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  9. Acyl group
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  10. What type of molecule is ethyl formate?
    EsterImage Upload 5
  11. Reduction of an Acyl Chloride to an Aldehyde
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  12. Reduction of an Ester to an Aldehyde
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  13. Reduction of a Nitrile to an Aldehyde
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  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
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  20. More functional groups
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  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
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  26. Imine formation—reaction with a primary amine
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  27. Oxime formation—reaction with hydroxylamine
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  28. Enamine Formation
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  29. Amine reactions
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  30. Cyanohydrin formation
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  31. Wittig reaction
    Image Upload 22Overall result is of this synthesis is:Image Upload 23
  32. Horner–Wadsworth–Emmons modification
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  33. Oxidation of aldehydes
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Card Set
Organic Chemistry
Exam 3 Organic chemistry II