Ochem_CH17_Alcohols

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lukemlj
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73229
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Ochem_CH17_Alcohols
Updated:
2011-03-20 05:27:13
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Ochem Alcohols
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Ochem Alcohols
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  1. Reduction of Aldehyde
  2. Reduction of Ketones
  3. Reduction of Esters
  4. Reduction of Carboxylic Acids
  5. Addition to Carbonyl
  6. Addition to Carbonyl
  7. Addition to Carbonyl
  8. Addition to Carbonyl
  9. Preparation - Markovnikov
  10. Preparation: Non-Markovnikov
  11. Preparation: Expoxide
  12. Preparation: Hydroxylation
    
  13. Dehydration: Tertiary
  14. Dehydration: Secondary and Tertiary
  15. Oxygenation: Primary Alcohols
  16. Oxygenation: Primary Alcohols
    • Also KMnO4 and K2Cr2O7
  17. Oxygenation: Secondary Alcohols
    • Also CrO3, KMnO4 and K2Cr2O7
  18. Oxidation of Phenols: Fremy's Salt
  19. More Fremy's Salt
  20. Tertiary Alkyl Halide
  21. Alkyl Halide from primary or secondary
  22. Another alkene to alcohol, Mark
  23. Another alkene to cis diol
  24. What functional groups are reduced to a primary alcohol?
    aldehyde, ester, and carboxylic acid
  25. A ketone is reduced to a ____ alcohol.
    secondary
  26. NaBH4 does not reduce ___ or ___
    Esters or carboxylic acids
  27. What are two products of a conjugated carbonyl and NaBH4?
  28. LiAlH4 is ____ reactive than NaBH4.
    more
  29. LiAlH4 reacts explosively with ___ and ___. It uses ___ ____ solvents instead
    ROH and H20, polar aprotic (ether, THF, dioxane)
  30. The nucleophile in NaBH4 and LiAlH4 is___. It attacks the ____ group and creates a ____ intermediate.
    Hydride; carbonyl, tetrahedral
  31. What are the incompatible functional groups for Grignard addition resulting in alcohols? Why?
    • -OH, -NH2, -COOH, -SH, -CN, -NO2, -SOOH
    • Acidic hydrogens react with CH3, a strong base.
  32. Tosylate review p.359
  33. Dehydration of an alcohol to an alkene is what kind of a reaction? What kind of intermediate does it involve?
    Review this mechanism.
    E1 reaction; carbocation intermediate
  34. Dehydration of 2nd and tertiary alcohol with ____ in ___ is what kind of reaction? Review this mechanism.
    • POCl3, pyridine
    • E2
  35. Oxidation of a primary alcohol yields ____.
    an aldehyde or a carboxylic acid
  36. Oxidation of a secondary alcohol yields ___
    a ketone
  37. Oxidation of a tertiary alcohol yields ____.
    No reaction
  38. What are four common oxidizing agents for alcohols? Which is the weakest?
    • Jones: CrO3, H2SO4 (H+); acetone
    • Dichromate: K2Cr2O7, H+; H2O
    • KMnO4; Base (e.g. NaOH)
    • PCC; CH2Cl2
    • PCC is the weakest
  39. PCC oxidizes a primary alcohol to what? The other 3 yield what?
    • Aldehyde
    • Carboxylic acid
  40. All 4 oxidizers yield what from a secondary alcohol?
    ketone
  41. What do all 4 oxidizers yield with a tertiary alcohol?
    No Reaction
  42. The 4 oxidizers apply to what kind of carbons?
    sp3
  43. Review Jones' mechanism
  44. What is used to "protect" alcohols?
    • TMS-Cl
    • Cl-Si(CH3)3
  45. R-OH + TMS-Cl yields what? What is it stable to? What cleaves it?
    • R-O-TMS
    • Stable to Ox, Red, Basic
    • Cleaved by acidic conditions
  46. Addition of a Grignard reagent to formaldehyde yields a ____; to an aldehyde yields a ___; to a ketone or an ester yields a ___.
    Primary alcohol, secondary alcohol, tertiary alcohol.
  47. Alcohols are often "protected" by the formation of ___.
    trimethylsilyl (TMS) ethers
  48. Alcohols can be ___ to give alkenes by treatment with ___ and can be transformed into alkyl halides by treatment with ___ or ___.
    dehydrated, POCl3, PBr3, SOCl2
  49. Alcohols are ___ acidic with pKa of about ___ and react with ___ bases and alkali metals to form ___.
    weakly, 16, strong, alkoxide anions
  50. Perhaps the most important reaction of alcohols is their ___ to carbonyl compounds.
    oxidation
  51. Primary alcohols are oxidized to ___ , secondary to ___, and tertiary to ___.
    aldehydes or carboxylic acids; ketones; no reaction.
  52. ___ is in ___ is often used for ___ primary alcohols to ___ and secondary alcohols to ___.
    PCC, dichloromethane, oxidizing, aldehydes, ketones
  53. A solution of ___ in ___ is frequently used for ___ primary alcohols to ___ and secondary alcohols to ___.
    CrO3, aqueous acid, oxidizing, aldehydes, ketones
  54. In a phenol, substitution of the aromatic ring by an EWG ___ acidity.
    increases
  55. Phenols can be ___ to ___ with Fremy's salt which can be reduced to ___ by reaction with ___.
    oxidized, quinones, hydroquinones, NaBH4

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