Organic Chemistry Chp. 18

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jhon1599
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103880
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Organic Chemistry Chp. 18
Updated:
2011-09-23 20:10:52
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organic chemistry Wade Jr
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Aldehydes and Ketones
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  1. What are two differential effects between aldehydes and ketones and how do they effect reactivity?
    • Inductive effects: contribution of e- density to the reactive site.
    • Steric effects: physical crowding of reactive site.
    • Inductive and steric effects make ketones more stable and less reactive than aldehydes.
  2. What reactions are used in chp 18?
    • LiAlH4
    • NaBH4
    • RMgX
    • Ozonolysis
    • PCC
    • Na2Cr2O7
    • H2SO4
    • Wittig reaction
    • Formation of hydrates, cyanohydrins
    • Formation of imines
    • Formation of acetals
  3. What is the main group name and the substituent name of aldehydes?
    Main group -al, substituent (formyl)
  4. What is the main group name and the substituent name of ketones?
    Main group -one, substituent (oxo)
  5. Name the functional groups in decreasing priority?
    • Carboxcylic acids
    • Esters
    • Amides
    • Nitriles
    • Aldehydes
    • Ketones
    • Alcohols
    • Amines
    • Alkenes
    • Alkynes
    • Alkanes
    • Ethers
    • Halides
  6. What charge does a Hydride (H:-) have?
    Negative one.
  7. Lithium aluminum hydride (LiAlH4):
    • Performs hydride reductions
  8. Sodium borohydride (NaBH4):
    • Performs hydride reductions
  9. How do you asses the oxidation state?
    • Degree of oxygen around carbon.
    • CH4 < C-OH < C=O < OH-CH=O < O=C=O
  10. Grignard reagents (R-Mg+-Br-):
    • Can form new C-C bonds
    • 2 step process, oxyanion formed (R3C-O-), quench with water (H3O+), result R3C-OH
  11. Ozone (O3):
    • Perfomrs ozonolysis
    • R2C=CR2 => 2 [R2C=O]
    • R'C CR => OH-R'C=O & OH-RC=O
  12. Sodium chromate (Na2Cr2O7) / H2SO4:
    • Performs oxidation
    • Must have -H to carry out reaction
    • Can have oxidation states starting at 6 going down to 3 and 4
    • Aldehydes can go all the way to carboxcylic acids (OH-RC=O)
  13. Pyridinium chlorochromate (PCC):
    • Performs oxidation
    • Must have -H to carry out reaction
    • Stops at aldehyde stage
  14. Wittig Reaction:
    • Three steps:
    • Preparation of the phosphonium salt of the tertiary phosphine and the halide;
    • Formation of the “ylide” from treating “#1” with strong base
    • Reaction of the ylide with the carbonyl compound to give the alkene.

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