Organic Chemistry Chapter 20 Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

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tulipyoursweety
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Organic Chemistry Chapter 20 Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction
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2014-03-31 05:03:59
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organic chemistry chapter 20 carbonyl organometallic
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Organic Chemistry Chapter 20 Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction
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  1. Reduction:
    ketone/aldehyde --?--> 1°/2° OH
    3 ways
    • NaBH4, CH3OH
    • or
    • 1) LiAlH4, 2) H2O
    • or
    • H2, Pd/C
  2. α,β-unsaturated aldehyde/ketone --(NaBH4, CH3OH)-->
    • allylic alcohol
    • (reduction of C=O) bond only
  3. acid chloride --?--> 1° OH
    • 1) LiAlH4, 2) H2O
    • LiAlHis a strong reducing agent and reduces acid chloride to a 1° OH
  4. acid chloride --?--> aldehyde
    • 1) LiAlH[OC(CH3)3]3, 2) H2O
    • milder reducing agent
    • reduction stops at aldehyde stage
  5. ester --?--> 1° OH
    • 1) LiAlH4, 2) H2O
    • strong reducing agent
  6. ester --?--> aldehyde
    • 1) DIBAL-H, 2) H2O
    • milder reducing agent
  7. carboxylic acid --?--> 1° OH
    1) LiAlH4, 2) H2O
  8. amide --?--> amine
    1) LiAlH4, 2) H2O
  9. aldehyde --?--> carboxylic acid
    • CrO3 or Na2Cr2O7 or K2Cr2O7 or KMnO4 with H2SO4, H2O reacts with 1° and 2° OH also
    • Ag2O, NH4OH only reacts with aldehydes
  10. How do you prepare organolithium reagents?
    R-Li
    R-X + 2 Li --> R-Li + LiX
  11. How do you prepare Grignard reagents?
    R-Mg-X
    R-X + Mg --(CH3CH2)2O--> R-Mg-X
  12. How do you prepare Organocuprate reagents?
    R-Li
    R2CuLi
    • R-X + 2 Li --> R-Li + LiX
    • 2 R-Li + CuI --> R2CuLi + LiI
  13. How do you prepare lithium and sodium acetylides?
    R-CΞC Na
    R-CΞC-Li
    • R-CΞCH --(NaNH2)--> R-CΞC Na + NH3
    • R-CΞCH --(R'Li)--> R-CΞC-Li + R'H
  14. With what do organometallic reagents act as bases?
    R-M 
    RLi, RMgX, R2CuLi
    H2O, ROH, RNH2, R2NH, RSH, RCOOH, RCONH2, RCONHR
  15. Organometallic reactions:
    alehyde/ketone --?--> 1°, 2°, or 3° OH
    • 1) RMgX or RLi, 2) H2O
    • adds H and R across the double bond
  16. Organometallic reactions:
    esters --?--> 3° OH
    • 1) RLi or RMgX (2 equivalents), 2) H2O
    • adds two R's to the carbonyl carbon
  17. Organometalic Reactions:
    acid chloride --?--> 3° alcohol
    • 1) RLi or RMgX (2 equivalents), 2) H2O
    • more reactive
    • adds two equivalents of R to acid chloride to form 3° OH
  18. Organometallic reactions:
    acid chloride --?--> ketone
    • 1) R2CuLi, 2) H2O
    • less reactive
    • add only one equivalent of R to form ketone
  19. Organometallic reactions:
    Carboxylation:
    R-? --(1) CO2, 2) H3O+)--> carboxylic acid
    R-MgX
  20. Organometalic reactions:
    epoxide --?--> alcohol
    • 1) RLi, RMgX, or R2CuLi
    • 2) H2O
  21. organometallic:
    α,β-unsaturated aldehydes and ketones
    --?--> allylic alcohol
    • 1) RLi or RMgX, 2) H2O
    • more reactive reagents
    • 1,2 addition
  22. organometallic:
    α,β-unsaturated aldehydes and ketones
    --?--> ketone
    • 1) R2CuLi, 2) H2O
    • Less reactive reagent
    • 1,4 addition
  23. How do you protect an alcohol during synthesis?
    • R-OH + Cl-TBDMS --> R-O-TBDMS
    • tert-butyldimethylsilyl ether
  24. How do you deprotect and reform an alcohol?
    R-O-TBDMS --(CH2CH2CH2CH2)4NF--> ROH + F-TBDMS
  25. DIBAL-H effect on aldehydes and ketones is...
    reduces them to 1° OH
  26. Acid chloride --(1) NaBH4, 2) H2O)--> ?
    1° OH
  27. Carboxylic acid/amides & derivatives --(NaBH4)--> ?
    No reaction

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