Ochem_CH17_Alcohols

  1. Reduction of Aldehyde
    Image Upload 2
    Image Upload 4
  2. Reduction of Ketones
    Image Upload 6
    Image Upload 8
  3. Reduction of Esters
    Image Upload 10
    Image Upload 12
  4. Reduction of Carboxylic Acids
    Image Upload 14
    Image Upload 16
  5. Addition to Carbonyl
    Image Upload 18
    Image Upload 20
  6. Addition to Carbonyl
    Image Upload 22
    Image Upload 24
  7. Addition to Carbonyl
    Image Upload 26
    Image Upload 28
  8. Addition to Carbonyl
    Image Upload 30
    Image Upload 32
  9. Preparation - Markovnikov
    Image Upload 34
    Image Upload 36
  10. Preparation: Non-Markovnikov
    Image Upload 38
    Image Upload 40
  11. Preparation: Expoxide
    Image Upload 42
    Image Upload 44
  12. Preparation: Hydroxylation
    Image Upload 46
    Image Upload 48
  13. Dehydration: Tertiary
    Image Upload 50
    Image Upload 52
  14. Dehydration: Secondary and Tertiary
    Image Upload 54
    Image Upload 56
  15. Oxygenation: Primary Alcohols
    Image Upload 58
    Image Upload 60
  16. Oxygenation: Primary Alcohols
    Image Upload 62
    • Image Upload 64
    • Also KMnO4 and K2Cr2O7
  17. Oxygenation: Secondary Alcohols
    Image Upload 66
    • Image Upload 68
    • Also CrO3, KMnO4 and K2Cr2O7
  18. Oxidation of Phenols: Fremy's Salt
    Image Upload 70
    Image Upload 72
  19. More Fremy's Salt
    Image Upload 74
    Image Upload 76
  20. Tertiary Alkyl Halide
    Image Upload 78
    Image Upload 80Image Upload 82
  21. Alkyl Halide from primary or secondary
    Image Upload 84
    Image Upload 86
  22. Another alkene to alcohol, Mark
    Image Upload 88
    Image Upload 90
  23. Another alkene to cis diol
    Image Upload 92
    Image Upload 94
  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?
    Image Upload 96
  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
Author
lukemlj
ID
73229
Card Set
Ochem_CH17_Alcohols
Description
Ochem Alcohols
Updated