Ochem 4th quiz

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Author:
lacythecoolest
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290508
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Ochem 4th quiz
Updated:
2014-12-03 04:24:42
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aldehydes ketones carboxylicacidderivatives
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rxn of aldehydes and ketones rxns of carboxylic acid derivatives, rxns of a,b-unsat carbonyl compounds
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  1. what needs to happen to aldehydes and ketones for a rxn to happen?
    addition of nucleophile to carbonyl carbon
  2. suffix and prefix of aldehydes
    systematic & common
    • -anal systematic
    • -aldehyde common
    • meth-, eth-, ect systematic 
    • formyl-, acetyl-, ect common
  3. suffix and prefix of ketones
    • -anone
    • oxo-
  4. 0=O=0
    1,2 cyclohexanedione
  5. C-C-C
        =O
    2-propanone acetone
  6. 2 ketones nomenclature
    what to remember with naming ketones
    • dione
    • must have # associated with it
  7. aldehyde vs. ketone
    aldehyde
  8. ketone vs. carboxylic acid
    carboxylic acid
  9. C-C-C-C-OH
         =O   =O
    3-oxopropanoic acid
  10. MEK
    • C-C-C-C
    •      =O
  11. MVK
    • C-C-C=C
    •      =O
  12. C-C-C=O
       -Br
    • 2-bromopropanal
    • a-bromopropionaldehyde
  13. R-CH
        =O
    ALDEHYDE
  14. R-C-OCH
         =O
    • ESTER
    • -oate
  15. C-C-C
        =O
    PROPANONE
  16. C-C-C-C-C
         =O
    2-pentanone
  17. C-C-C-C-C-C
        =O  =O
    2,4-hexanedione
  18. C-C=C-C-C-C
                    =O
    4-hexen-2-one
  19. molecule most commonly used for Grignards
    Mg
  20. O=0->0-0
               -OH
    • 1. O-MgBr
    • 2. H+, H2O
  21. Ketone/aldehyde + Grignard=
    alcohol
  22. relative reactivates of carbonyl compounds
    most->least
    • acyl halide
    • acid anhydride
    • aldehyde
    • ketone
    • ester~carboxylic acid
    • amide
    • carboxylate ion
  23. nomenclature priority
    highest -> lowest
    CEANAAK5AEA
    • carboxylic acid
    • ester
    • amide
    • nitrile
    • aldehyde
    • ketone
    • alcohol
    • amine
    • alkene
    • alkyne
    • alkane
    • alkyl halide
  24. Grignard reagent of aldehyde or ketone
    A/K + R-MgBr ~>CH3CH2O(-) ~H3O+~>(alcohol) CH3CH2OH
  25. CCCCH~?~>CCCC-OH
           =O               -0
    • 1.0-MgBr
    • 2. H3O+
  26. What to remember with Grignard and asymmetric centers
    will be a racemic mixture
  27. Grignard and esters
    ester~(CH3MgBr)~>ketone~>~(CHMgBr)~>R-C(2C)-O-*~(H3O+)~>R-C(CC)-OH (tertiary alcohol)
  28. what group is eliminated from an ester's tetrahedral intermediate with Grignard?
    -OCH3
  29. what are the 2 intermediates of ester with grignard
    • 1. ketone
    • 2. tertiary alkoxide ion
  30. Grignard with carbon dioxide
    carboxylic acid
  31. O=C=O ~?~>CCC-OH
                              =O
    • 1. CCCMgBr
    • 2. H3O+
  32. CCC-OCH~?~>(tert)RCCCOH
         =O
    • 1.CH3MgBr(x2)
    • 2. H3O+
  33. Grignard + acyl chloride
    tertiary alcohol
  34. CCCC=O~?~>CCCC(tert)-CC-CC-OH
           -Cl
    • 1. 2 CCMgBr
    • 2. H3O+
  35. Grignard + aldehyde=
    vs.
    Grignard + ketone=
    • secondary alcohol
    • tertiary alcohol
  36. carbonyl + acetylide ion
    nucleophilic addition product
  37. CCCH=O~?~>CCC(-OH)C(trip=_)N
    • 1.:CN-
    • 2. H+
  38. CCCH=O~?~>CCC(-OH)CNH2
    • 1. :CN-
    • 2. Raney Ni/H2
  39. cyanohydrin~?~>alpha-hydroxycarboxylic acid
    HCl, H2O/heat
  40. ketone/aldehyde + hydride ion
    solvent & products
    • 1. NaBH4
    • 2. H3O+
    • Ketone: secondary alcohol
    • Aldehyde: primary alcohol
  41. 2 hydride ions
    • NaBH4
    • LiAlH4
  42. which carbonyl groups use NaBH4?
    • Aldehyde
    • ketone
    • acyl chloride
  43. carbonyl groups that react with LiAlH4
    • Ester
    • carboxylic acid
    • amide
  44. aldehyde~?~>primary alcohol
    • 1. NaBH4
    • 2. H3O+
  45. Ketone~?~>secondary alcohol
    • 1. NaBH4
    • 2. H3O+
  46. acyl chloride~?~>primary alcohol
    • 1. 2NaBH4
    • 2. H3O+
  47. acyl chloride~?~>aldehyde
    • 1.LiAl[OC(CH3)3]H
    • 2. H2O
  48. ester~?~>2 primary alcohols
    • 1. 2LiAlH4
    • 2. H3O+
  49. rxn of ester  with hydride ion
    ester->aldehyde->primary alcohol
  50. carboxylic acid ~?~>primary alcohol
    • 1. LiAlH4
    • 2. H3O+
  51. rxn of carboxylic acid with hydride ion
    carboxylic acid->ALDEHYDE->alcohol
  52. rxn of amide with hydride ion
    • amide->imine->amine
    • 1. LiAlH4
    • 2. H2O
  53. partial ester removal to aldehyde
    • 1. DIBALH -78
    • 2. H2O
  54. which two carbonyl groups undergo 2 successive reactions with hydride ion and Grignard?
    acyl chlorides and esters
  55. aldehyde/ketone ~?~>imine
    NH3
  56. aldehyde/ketone~?~>enamine
    • secondary amine
    • ph 4-5
  57. what is a hydrate?
    molecule with 2 OH groups to same carbon
  58. alcohol added to ketone or aldehyde
    • hemiacetal
    • acetal

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