Reactions of Enolate Anions

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Author:
enger91
ID:
85463
Filename:
Reactions of Enolate Anions
Updated:
2011-05-12 13:40:51
Tags:
enolate anion organic chemistry
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University of MN Twin Cities, CHEM 2302
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  1. Simple Aldol Condensation
    ketone + LDA-> enolate (R-CH--C(=O)-R) + ketone + H2O-> R-C(=O)-CH(R)-C(OH)-(R)2 + heat-> R-C(=O)-CR=C-(R)2
  2. ketone + LDA->
    enolate
  3. ketone --> enolate
    LDA
  4. enolate + ketone + H2O, heat->
    R-C(=O)-CR=C-(R)2
  5. aldehyde + LDA->
    R-CH--CHO
  6. aldehyde --> R-CH--CHO
    LDA
  7. R-CH--CHO + R-Br->
    (R)2-CH-CHO
  8. R-CH--CHO --> (R)2-CH-CHO
    R-Br
  9. R-C(=O)-CH3 + 3I2, 3NaOH, heat->
    R-C(=O)-CI3
  10. R-C(=O)-CH3 --> R-C(=O)-CI3
    3I2, 3NaOH, heat
  11. R-C(=O)-CI3 + H2O, heat->
    acid + HCI3
  12. R-C(=O)-CI3 --> acid + HCI3
    H2O, heat
  13. R-CH2-C(=O)-O-R + H3CONa->
    R-CH--C(=O)-O-R
  14. R-CH2-C(=O)-O-R --> R-CH--C(=O)-O-R
    H3CONa
  15. R-CH--C(=O)-O-R + R-CH2-C(=O)-O-R->
    R-C(=O)-CH(R)-COOR
  16. ester + H3O+, boil->
    acid
  17. For a mixed reaction...
    one reactant must have no enolizable H.
  18. R-C(=O)-CH2-C(=O)-OR + CH3ONa->
    R-C(=O)-CH--C(=O)-OR
  19. R-C(=O)-CH2-C(=O)-OR --> R-C(=O)-CH--C(=O)-OR
    CH3ONa

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