Ochem-Ch19-Aldehyde-Ketone

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  1. What suffix is used for naming an aldehyde?
    -al
  2. What suffix is used for a an aldehyde attached to a ring?
    -carbaldehyde
  3. Formaldehyde
    HCHO
  4. Acetaldehyde
    CH3CHO
  5. What suffix is used for a ketone?
    -one
  6. Acetone
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  7. acyl group
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  8. Acetyl
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  9. How are Aldehydes normally prepared?
    • Oxidation of primary alcohols
    • Partial reduction of esters
  10. How are Ketones normally prepared?
    • Oxidation of secondary alcohols
    • Addition of diorganocopper reagents to acid chlorides
  11. What is the most common reaction of aldehydes and ketones?
    Nucleophilic addition reaction
  12. What reagents are used to reduce aldehydes and ketones?
    NaBH4 or LiAlH4
  13. Aldehydes and ketones are reduced by NaBh4 or LiAlH4 to yield ____ and ____ alcohols respectively.
    secondary, primary
  14. Addition of Grignard reagents to aldehydes and ketones gives ____ and ___ alcohols respectively.
    tertiary, secondary
  15. Addition of HCN to aldehydes and ketones yields ___.
    cyanohydrins
  16. Primary amines add to carbonyl compounds yielding ___.
    imines
  17. Secondary amines to carbonyl compounds yield ____.
    enamines
  18. Reaction of an aldehyde or ketone with hydrazine and base gives _____.
    an alkane (wolff-kishner reaction)
  19. Alcohols add to carbonyl groups to yield ___ which act as ____.
    acetals, protecting groups
  20. Phosphoranes add to aldehydes and ketones to give ___.
    alkenes (Wittig reaction)
  21. Alpha,beta-Unsaturated aldehydes and ketones often react with nucleophiles to give the product of ____ or ___.
    conjugate addition; 1,4-addition
  22. Alpha,beta-Unsaturated aldehydes and ketones react with a diorganocopper reagent resulting in the addition of ___, ___, or ___ to the double bond.
    alkyl, aryl, or alkenyl group
  23. Preparation
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  27. Oxidation
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  28. Secondary alcohol to ketone
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  31. Partial Reduction
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  33. Oxidation
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    • Also can use KMnO4 and hot HNO3
  34. Aldehydes are easily oxidized to yield ___, but ketones are generally ___ toward oxidation. This is because aldehydes have a -CHO ___, while ketones do not.
    • carboxylic acids, inert.
    • proton
  35. Tollens' reagent
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  36. Ketone Cleavage
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  37. Formation of gemdiol by hydration occurs when an aldehyde or ketone is treated with a nucleophile H-Y, where Y is ___ and can stabilize a negative charge. Examples of Y include ____.
    • electronegative
    • -OH, -OR, -Cl, -Br, -HSO4(-)
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    • Can do the "same" with Aldehyde and LiAlH4 (and ether solvent) to get a primary alcohol
    • Not reversible
  40. Stoichometry
    4 Ald/Ket + 1 NaBH4 (LiAlH4) ->
    4 Alcohol
  41. Stereochemistry of Hydride attack on cyclohexal?
    Equatorial favored 90% of time.
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    • X: Cl, Br, I (not F)
    • R'': Alkyl, vinly, aryl, alkynyl
    • Incompatible with R-OH, H2O, -COOH, -NH2
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    • Note: C-C bond formed
  44. Image Upload 39----H3O+---->
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    • Imine
    • Need some acid, but not too much
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    • Enamine
    • Need some acid, but not too much
  47. Wolff-Kishner
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  48. Addition of alcohols
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  49. Wittig
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  50. Alpha/Beta
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  51. Alpha/Beta
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  52. Alpha/Beta
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  53. Test for Ketone
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    • Oxime
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  54. Test for Acetone
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    • Dinitrophenylhydrazone
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  55. Acetal Formation
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    • Completely reversible
  56. Under what conditions are ketals stable?
    Neutral or basic
  57. How would you protect a keto group during reduction?
    • Convert to acetal/ketal with 2 R-OH and HCl catalyst or diol.
    • Reduce with LiAlH4.
    • Remove acetal with aqueous acid.
  58. Cannizzaro Reaction
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  59. Raney-Ni
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Author
ID
73832
Card Set
Ochem-Ch19-Aldehyde-Ketone
Description
Ochem-Ch19-Aldehyde-Ketone
Updated
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