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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 2Acyl 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)

    Image Upload 4
  8. Acul chrolide -----> aldehyde
    ester -----> Aldehyde
    Nitrile -----> aldehyde
    Image Upload 6
  9. Acyl group
    Image Upload 8
  10. What type of molecule is ethyl formate?
    EsterImage Upload 10
  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
    Image Upload 16
  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...
    Ketone
  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
    Image Upload 18
  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
    Image Upload 22
  26. Imine formation—reaction with a primary amine
    Image Upload 24
  27. Oxime formation—reaction with hydroxylamine
    Image Upload 26
  28. Enamine Formation
    • Image Upload 28
    • Image Upload 30Image Upload 32
  29. Amine reactions
    Image Upload 34Image Upload 36
  30. Cyanohydrin formation
    • Image Upload 38Image Upload 40
    • Image Upload 42
  31. Wittig reaction
    Image Upload 44Overall result is of this synthesis is:Image Upload 46
  32. Horner–Wadsworth–Emmons modification
    Image Upload 48
  33. Oxidation of aldehydes
    Image Upload 50
Author
Physis
ID
17773
Card Set
Organic Chemistry
Description
Exam 3 Organic chemistry II
Updated

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