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2011-10-31 22:27:42
Chem ch14 15

Chapters 14 & 15
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  1. A compound that contains an –OH (hydroxyl) group bonded to a tetrahedral carbon
  2. are alcohols, non-polar or polar
  3. they are associated by hydrogen bonding in liquid state
  4. alcohols have high or low boiling points?
    high due to hydrogen bonding
  5. Boiling points also increase with increasing molecularweight (increased London dispersion forces)
    -the higher the chair, the higher to bp
  6. are more soluble in water than hydrocarbons ofsimilar molecular weight (due to H-bonding with water).
    - the more non-polar the less soluble in water
  7. 1. No reaction with strong bases
    2.Dehydration to form alkenes
    3.Oxidation to aldehydes, ketones, and carboxylic acids
  8. phenol DOES react with
    a strong base (strong base NaOH)
  9. Elimination of a molecule of water from adjacent carbon atoms gives an alkene.
    is most often brought about by heating
  10. 1o are the most difficult to dehydrate and require ___ temperatures
  11. 2o undergo acid-catalyzed dehydration at somewhat ___ temperatures than 1o
  12. 3o generally undergo acid-catalyzed dehydration at temperatures only slightly ____ above room temperature
  13. in dehydration of alcohols: the alkene with the product with the MOST alkyl groups is called
    major product
  14. in dehydration of alcohols, the alkene product with the lower amount of alkyl groups is called the
    minor product
  15. in dehydration-hydration of alcohols the reactant side has a + H2O makes the arrow favor what side
    right -->
  16. in dehydration-hydration of alcohols the reactant side has a - H2O the arrow favors what side?
    left <-----
  17. (loss of H or gain of O)
  18. Oxidation of a 1o alcohol gives an
    • aldehyde or a carboxylic acid
    • 1st aldehyde then final product carboxylic acid
  19. oxidation of alcohol is commonly carried out using
  20. oxidation of a 2o alcohol gives a
  21. Oxidation of tertiary alcohols are
    reistant to oxidation N.R.
  22. It is sometimes possible to stop the oxidation at the aldehyde stage by
  23. oxygen atom bonded to two carbon atoms.
  24. use common names to name these molecules
  25. An ether in which one of the atoms in a ring is oxygen.
    Cyclic ethers
  26. Ethylene oxide
  27. Tetrahydrofuran (THF)
  28. polar compounds, but weak dipole-dipole bodning
  29. low boiling points and low molecular weight
  30. they do not react with oxidation agents
    they do not react with reducing agents
    they are not affected by most acids or bases
  31. inertness
    stable, and unreactive. helps disolve things but does not react (like a catalyst)
  32. a compound containing an sulfhydrhyl group (SH)
  33. these are stinky,
    have low molecular weights.
    nonpolar covalent.
    no hydrogen bonding
    low bp.
    less soluble in water than alcohols
  34. mercaptan
    means you have a thiol
  35. these react with strong bases such as NaOH to from water-soluble salts
  36. NaOH base H2O> salt + water
    Thiol reacts with strong base always have a salt and water as product
  37. Thiols are readily oxidized to disulfides (s-s) by
  38. Oxidation of thiols
    you take the H off and combine the a diplicate molecule by attaching the Ss together
  39. Nonsuperposable mirror images
    they are different molecules
  40. one object either the original object or the mirror object.
    ex: hand
  41. a carbon with four different groups bonded to it
  42. an object that its mirror image is superposable, then they are identical and called
  43. a mixture of equal amounts of two enantiomers
    racemic mixture
  44. always comes in pairs
  45. to assign a name to enantiomers
    step 1: is it stereocenter?
    step 2: assign priority of atoms directly attacted to stereocenter ( if same then go to next atom of that molecule) look @ P.table the higher atomic number the higher the priority
    step 3: the lowest priority (4) has to face back
    step 4: draw arrows from 1,2,3
    step 5: if arrows turn right then R if arrows turn left then S
  46. if the lowest priority of enantiomer to assign R or S is not facing back then just go through all steps and switch the S, or R at the end
  47. for a molecule with n stereocenters the maximum number of possible steroiomers is
    • 2n
    • ex: there are 2 stereocenters in molecule. so its 22 = 4
  48. stereoisomers that are not mirror images but attachments are the same
    • diastereomers:
    • so just take one chiral from an enantiomer and another chiral from a different enantiomer to get diastereomers
  49. light waves vibrating only in parallel planes
    narrows light down
    plane of polarized light
  50. showing that a compound is capable of rotating the plane of plan-polarized light
    rotates light
    • optically active
    • use a polarimeter to change/roate light direction
  51. clockwise rotation of the plane of plane-polarized light indicated by +
  52. counterclockwise rotation of the plane of plane-polarized light indicated by -