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2011-03-19 18:36:26
Ochem Ch19 Aldehyde Ketone

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  1. What suffix is used for naming an aldehyde?
  2. What suffix is used for a an aldehyde attached to a ring?
  3. Formaldehyde
  4. Acetaldehyde
  5. What suffix is used for a ketone?
  6. Acetone
  7. acyl group
  8. Acetyl
  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 ___.
  16. Primary amines add to carbonyl compounds yielding ___.
  17. Secondary amines to carbonyl compounds yield ____.
  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
  24. Oxidation
  25. Secondary alcohol to ketone
  26. Partial Reduction
  27. Oxidation
    • Also can use KMnO4 and hot HNO3
  28. 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
  29. Tollens' reagent
  30. Ketone Cleavage
  31. 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(-)
    • Can do the "same" with Aldehyde and LiAlH4 (and ether solvent) to get a primary alcohol
    • Not reversible
  32. Stoichometry
    4 Ald/Ket + 1 NaBH4 (LiAlH4) ->
    4 Alcohol
  33. Stereochemistry of Hydride attack on cyclohexal?
    Equatorial favored 90% of time.
    • X: Cl, Br, I (not F)
    • R'': Alkyl, vinly, aryl, alkynyl
    • Incompatible with R-OH, H2O, -COOH, -NH2
    • Note: C-C bond formed
  34. ----H3O+---->
    • Imine
    • Need some acid, but not too much
    • Enamine
    • Need some acid, but not too much
  35. Wolff-Kishner
  36. Addition of alcohols
  37. Wittig
  38. Alpha/Beta
  39. Alpha/Beta
  40. Alpha/Beta
  41. Test for Ketone
    • Oxime
  42. Test for Acetone
    • Dinitrophenylhydrazone
  43. Acetal Formation
    • Completely reversible
  44. Under what conditions are ketals stable?
    Neutral or basic
  45. 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.
  46. Cannizzaro Reaction
  47. Raney-Ni