Orgo Notes Ch 10

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  1. What is the least reactive functional group? __ can be converted into almost any functional group and vice versa. 

    What is the pKa of phenol? Of alcohols?
    • ethers
    • alcohols

    Phenol has a pKa of 10; alcohols of 16
  2. What does alcohol allow for?
    • water solubility
    • (good as anti-tumor agents)
  3. How are diols named?

    What does BP depend on?

    When you go below -20 degrees, what happens? What about at -78 degrees Celsius?
    • alkane diols
    • ex: pentane-1,2-diol

    hydrogen bonding (higher BP) and branching (lower BP due to inability to stack together)

    • you can no longer use water
    • at -78, you use acetone and dry ice
  4. Ether can __. It is __.

    In alcohols, what is the most acidic part of the molecule? Where do we try to push the reaction?
    hydrogen bond to water but not to itself; slightly soluble

    • -OH
    • ------->
  5. Why do we use metals? 

    Distinguish between the use of sodium and potassium?
    to form alkoxide ions

    Sodium is used with methyl and ethyl

    Potassium is used with secondary and tertiary because it reacts faster
  6. A lower pKa indicates what?

    True or False: 
    Resonance = electron-withdrawing.

    Sn2 uses __ as a nucleophile.
    Sn1 uses __ as a nucleophile.
    a higher acidity

    False: not equal

    • -OH
    • water
  7. What does THF do?

    Carbon can adopt __.

    What happens when you add a funcitonal group?
    soluble in water and acts as a cosolvent

    5 different oxidation levels

    carbon changes oxidation numbers
  8. Ethanol is oxidized to __ which is oxidized to __.

    Adding H2O across a double bond is neither __ nor __. Instead, it is __.
    • carbonyl
    • carboxylic acid

    • oxidation
    • reduction
    • hydration
  9. Grignard reagents act irreversibly with __. We don't want to use GRs as __, but __.

    __ is too reactive. __ is too unreactive.

    If there are no acidic protons, what will the GR behave as?
    • water
    • bases
    • nucleophiles
    • Iodide
    • Fluoride

    a nucleophile
  10. Epoxides behave somewhat as __. 

    What is the deal with epoxides and GRs attacking them?

    Epoxides can be made from __ and are probably the most reactive functional group.
    halonium ions

    it comes in from the opposite face, causing them to be trans to each other
  11. __ has a higher oxidation state than ketones. How many GRs are used? __ are more electrophilic than esters. 

    What is GR attack on acid derivatives called? 

    Leaving groups leave from what?
    • ester
    • two
    • ketones
    • nucleophilic allyl substitution
    • tetrahedral substances
  12. With epoxides, GRs come in where?

    What is an effective use of basicity?

    Adding hydride does what? (pathway)
    the path of least resistance (the R goes to the side opposite the most crowded side)

    D2O= labeling certain parts of the molecule

    • reduce the ketone--> alcohol 
    • reduce the carboxylic acid to a ketone and then an alcohol
  13. Hydride ions are __.
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Orgo Notes Ch 10
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