Ochem CH 17 exam 3

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ffloyd
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72093
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Ochem CH 17 exam 3
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2011-03-10 17:01:31
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OCHEM CH17 EXAM3 aldehydes ketones
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flashcards for CH 17 ochem exam 3
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  1. name this group
    \
    c=o
    /
    carbonyl group
  2. name this group
    R
    l
    C=O
    l
    H
    aldehyde
  3. name this group
    R
    l
    C=O
    l
    R
    ketone
  4. order of precedence in numbering:

    ______>_________>_____
    carbonyl > alcohol > alkene/alkyne

    C=O > OH > C=C C = C
  5. aldehydes have (-??) endings
    ketones have (-???) endings
    • aldehydes have (-al) endings
    • ketones have (-one) endings
  6. order of precedence in numbering:

    aldehydes ( ___ ) ketones
    aldehydes > ketones
  7. an aldehyde with a ketone as a substituent has what in its name?
    • "OXO"
    • ex: 5-oxohexanal
    • CH3C(O)CH2CH2CH2C(O)H
  8. an aldehyde attached to a ring structure has what ending?
    carbaldehyde

    ex: cyclopentanecarbaldehyde
  9. name this substituent
    O
    ll
    CCH3
    acetyl
  10. in a cyclic molecule, carbonyl always gets #___ and substituents always get _____ possible number
    in a cyclic molecule, carbonyl always gets #1 and substituents always get lowest possible number

  11. Common name & IUPAC name
    Common name : formaldehyde

    IUPAC name: methanal

  12. Common name & IUPAC name
    Common name: acetone

    IUPAC: propanone

  13. Common name & IUPAC name
    Common name: acetaldehyde

    IUPAC: ethanal

  14. Common name & IUPAC name
    Common name: acetophenone

    IUPAC name: 1-phenylethanone


  15. Common name
    diethyl ketone

  16. Common name
    methyl ethyl ketone
  17. Oxidation of alcohol:

    2o alcohol--(_____)->ketone
    2o alcohol--CrO3->ketone
  18. Oxidation of alcohol:
    1o alcohol--(_____)->aldehyde
    1o alcohol--PCC->aldehyde
  19. F-C acylation:

  20. Ozonolysis of Alkenes

  21. Hydration of Alkynes
  22. Aldehydes are _____ reactive than ketones
    MORE ; due to sterics & carbonyl polarization
  23. Electronegative substituents ________ reactivity of C=O
    INCREASE ; by intensifying + charge on C which allows greater reactivity with Nucleophiles
  24. Carbonyl & Nucleophilic Addition:

    If good Nucleophile =>
    If good Nucleophile = Nuc adds to C first, then O is protonated
  25. Carbonyl & Nucleophilic Addition:

    If weak Nucleophile=>
    If weak Nucleophile = O protonates first, then Nuc adds to C
  26. "hemiacetal" has ...
    "hemiacetal" has OH,OR on same C
  27. "acetal" has ...
    "acetal" has OR,OR on same C
  28. a "thiol" is ...
    a "thiol" is like an alcohol with S instead of O

    ex: R-OH => R-SH
  29. The 3 steps for using Protecting Groups:
    • 1) Protect carbonyl using ethylene glycol
    • 2) Undergo SN2 rxn
    • 3) Deprotect carbonyl with water and H+
  30. What is this compound and what is it used for?

    HO-CH2-CH2-OH
    ethylene glycol ; used as a Protecting Group to limit reactivity of carbonyls
  31. Name NH3
    ammonia
  32. CH3NH2 is a ____ amine
    primary
  33. (CH3)2NH is a ____ amine
    secondary
  34. (CH3)3N is a ____ amine
    tertiary
  35. Primary amine = ?
    Primary amine = "imine"
  36. The 2 steps for adding an amine to a carbonyl are . . .
    1) Addition of amine to C (N-C) causing e- in C=O d.b. to move to O as LPE and H+ to shift to O-

    2) Elimination of 1 eq H2O
  37. What is the net change when adding a primary amine to a carbonyl?

    R'
    l
    C=O + NH2R ----> ?
    l
    H
    Replace O by N and lose 2 H's from N

    • R'
    • l
    • C=NR
    • l
    • H
  38. Name H2N-NH2
    hydrazine
  39. Name
    \
    C=N-NH2
    /
    hydrazone
  40. Secondary amine = ?
    Secondary amine = "enamine"
  41. A Deoxygenation Reaction does what?
    replaces C=O with CH2
  42. Deoxygentation via Wolff Kishner Reduction is accomplished by adding what in 2 steps?

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