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OChem II quiz 3

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  1. Nomenclature: acids
    • -oic acid
    • ie. butanoic acid
  2. common name for meth group
    form-
  3. common name for eth group
    acet-
  4. a carbon double bonded to a oxygen
    carbonyl group
  5. carbonyl compound groups that can be replace by a nucelophile
    • Cl
    • OH
    • OR
    • NH2
    • NHR
    • NR2
  6. R-O-R
    ester
  7. carbonyl compound groups that cannot be replaced with a nucleophile
    • aldehyde
    • ketone
  8. RC=O
      H
    aldehyde
  9. RC=O
      R
    Ketone
  10. functional group on a carboxylic acid
    carboxyl group
  11. methanoic acid
    formic acid
  12. ethanoic acid
    acetic acid
  13. propanoic acid
    propionic acid
  14. butanoic acid
    butyric acid
  15. pentanoic acid
    valeric acid
  16. hexanoic acid
    caproic acid
  17. propenoic acid
    acrylic acid
  18. Greek letters 1-5
    • alpha
    • beta
    • gamma
    • delta
    • epsilon
  19. which nomenclature uses Greek letters
    common name
  20. first carbon to get alpha
    adjacent to carbonyl carbon
  21. Ring vs carboxylic acid
    carboxylic acid
  22. carboxylic acids OH replaced with X
    acyl chlorides
  23. nomenclature for acyl chlorides
    • -yl chloride
    • ie. carbonyl chloride
  24. carboxylic acid OH replaced with OR
    ester
  25. ester nomenclature
    • named first: R group attached to carboxyl oxygen and salts
    • -ate replaces -ic acid
  26. cyclic esters
    lactones
  27. lactone systematic nomenclature
    • oxacyclo-
    • -anone
    • ie. 2-oxacyclohexanone
  28. amide nomenclature
    replace -oic acid, -ic acid, -ylic acid
  29. what indicate that a substituent is bonded to a nitrogen
    preceding N to substituent
  30. cyclic amides
    lactams
  31. 3 compound types that are resonance contributors
    • Amides
    • Carboxylic acids
    • Esters
    • (double bonds resonate between electronegative atoms)
  32. carboxylic acids with long hydrocarbon chains
    fatty acids
  33. stage reactant becomes sp3 from sp2
    nucleophile adds to carbonyl carbon
    tetrahedral intermediate
  34. nucleophile replaced substituent attached to acyl group
    • acyl transfer reaction
    • nucleophilic acyl substitution reaction
    • nucleophilic addition-elimination reaction
  35. mechanism:
    nucleophilic add-elim rxn w/neg nucleophile
    • 1. nuc adds -> carbonyl carbon =tetrahedral intermediate
    • 2. weaker base elmin=pi bond - resonance
  36. Mechanism:
    nucleophilic add-elim rxn w/neutral nucleophile
    • 1. nuc->carbonyl carbon=tetra inter
    • 2. proton(H) removed from tet inter
    • 3. weaker base elmin=pi!
  37. Mechanism:
    Acyl chloride w/alcohol
    • 1. nucleophilic -OH->carbonyl carbon of acyl chloride=tet inter ether
    • 2. -H proton loss
    • 3. x-ion eliminated from deprotonated tet inter
    • base strength:
    • chloride ion<alkoxide ion
  38. what reacts with H2O to form carboxylic acid and alcohol?
    • esters
    • hydrolysis rxn
  39. ester + alcohol=
    • new ester and new alcohol
    • * alcoholysis rxn
    • transesterification rxn
  40. ester + amine
    • amide
    • aminolysis
  41. 1. Organic intermediates and products in acidic solutions are:

    2. these are not formed in acidic solutions:
    • 1. positively charged or neutral
    • 2. negatively charged organic intermediates and products
  42. 1. all organic intermediates and products in basic solutions are:

    2. these are not formed in basic solutions
    1. negatively charged or neutral

    2. positively charged organic intermediates and products
  43. Mechanism:
    acid-catalyzed ester hydrolysis
    • 1. acid protonates->carbonyl oxygen
    • 2. H2O(nucleophile)->carbonyl carbon of protonated carbonyl group=tet inter w/proton
    • 3. protonated tet inter in equilibrium w/non prot
    • 4. when nonprot is re-protonated it forms various intermediates
  44. Mechanism:
    hydrolysis of an ester w/tertiary alkyl group
    • 1. acid protonates carbonyl oxygen
    • 2. leaving group departs=tertiary carbocation
    • 3. nucleophile/H2O w/carbocation
    • 4. base takes proton from alcohol
  45. Mechanism:
    Transesterification
    ester + alcohol
    • 1. acid protonates carbonyl oxygen
    • 2. depart LG
    • 3. ROH nucleophile w carbocation
    • 4. proton from alcohol
  46. Mechanism:
    hydroxide-ion-promoted ester hydrolysis
    • 1. OH ->carbonyl carbon of ester
    • 2. CH3O (OH) eliminated
    • 3. FP: carboxylate ion and methanol
  47. compounds w/3 OH groups and 3 glycerol + w/fatty acid
    triglycerides

    R-CH2O-C(=O)-R x3x
  48. What is soap made of?
    • fat/oil + H2O-(NaOH)->
    • glycerol + sodium salts of fatty acids(soap)
  49. carboxylic acids have approximately the same reactivity as
    and react w/? to form them
    RXN name?(after famous person_
    • esters
    • COOH + alcohol=ester
    • (only in acidic solution)
    • Fischer esterification
  50. which two mechanisms are exactly reverse of each other?
    Fischer esterification & ester acid-cat hydrolysis
  51. VIP Acids from this section
    carboxylic acid
  52. VIP bases from this section
    amine
  53. carboxylic acid + amine
    nomenclature
    ammonium carboxylate salt
  54. what do amides react with?
    only H2O and alcohols in acidic conditions
  55. Mechanism:
    acid-cat amide hydrolysis and alcoholysis
    • 1. acid-H+->carbonyl oxygen
    • 2. H20(nucleo) added->carbonyl carbon=tetinter I & tetinter II
    • 3. re-protonate->oxygen=tetinter I or tetinter III(favored)
    • 4. IF tetinter III, NH3 elims
    • 5. NH3 protonated AFTER it leaves
  56. Mechanism
    hydroxide-ion-promoted hydrolysis of amides
    with 2 equiv. of OH
    * 2nd order
    • 1. first OH/nucleophile->carbonyl carbon
    • 2. second OH takes proton from tetinter
    • 3. -NH2 elimin=carboxylate ion
  57. the only two places an arrow comes from
    unpaired electrons or a bond
  58. the only two places an arrow from unpaired electrons goes to
    atom or bond
  59. the only place an arrow from a bond goes to
    an atom to make either a radical if split or unpaired electrons
  60. Mechanism:
    Synthesize primary amines
    hydrolysis of an imide
    -famous person name
    • Gabriel synthesis
    • 1. base takes proton from phthalimide N
    • 2. nucleophile ->alkyl halide
    • 3. hydrochop 2 amide bonds by acid
    • 4. acidic solution=alkyl ammonium ion & phthalic acid--(HO-)-->primary amine(only ones)
  61. compound w/2 acyl groups bonded to nitrogen
    imide
  62. compound that contains cyano group
    nitriles
  63. Nitrile systematic nomenclature
    common nomenclature
    special
    • Sys: add nitrile
    • Com: -onitrile (replaces -ic acid)
    • alkyl group + cyanide
  64. Special NItrile nomenclature
    alkane branch with tert carbon at end
    -cyclo w/shared double bonds

    C=CHC(=-)N
    • iso-  ie. isohexyl cyanide
    • phenyl cyanide

    acrylonitrile
  65. common name of 3-methylbutanoic acid
    C
    C-C-COOH
    C
    isovaleric acid
  66. Mechanism
    hydrolysis
    Nitrile --(HCl,H2O/heat)-->
    • 1. acid protonates nitro on cyano group
    • 2. oxygen -+H->base =neutral item
    • 3. protonated amide--(H2O/several steps)-->carboxylic acid
  67. catalytic hydrogenation
    • raney nickel metal catalyst, removes double/triple bonds
    • H2/raney nickle
  68. CH3CH2Br--------------->CH3CH2COOH
    list the two solutions and intermediate
    • S1: -C=-N/DMF
    • Intermed: CH3CH2C=-N
    • S2: HCl, H2O/heat
  69. what does the loss of water from 2 molecules of a carboxylic acid result in?
    • acid anhydride
    • carboxylic acid derivative
    • OH replaced w/-ROC=O|-R
  70. Anhydride nomenclature
    symmetric vs. mixed
    • sym: anhydride instead of acid
    • mixed: list acids names in alphabetical order and anhydride at end
  71. anhydride + alcohol=
    ester + carboxylic acid
  72. anhydride + water =
    x2 carboxylic acid
  73. anhydride + amine=
    amide + carboxylate ion
  74. Mechanism
    acid anhydride w/alcohol
    (acyl chloride w/alcohol)
    • 1. nucleo(ROH) adds ->carbonyl carbon =tetinter
    • 2. -proton from tetinter
    • 3. carboxylate ion elim
  75. Steps to activate carboxylic acids
    • 1. convert to acyl halide
    • COO-+ SOCl2 or PCl3 --heat--> RC=O|Cl + pieces

    2. Intermed: Cl ion + carbonyl carbon=tetinter (O->P/S)

    • 3. synthesize carboxylic acid derivatives
    • acyl halide + nucleophile=LOTS of cbxyc AD
  76. how to synthesize carboxylic acid derivatives
    acyl halide + nucleophile
  77. carbon double bonded to an oxygen
    carbonyl group
  78. carbonyl group attached to alkyl(R) or aromatic (Ar) group
    acyl group
  79. carboxylic acid derivatives
    • acyl chlorides
    • acid anhydrides
    • esters
    • amides
  80. cyclic esters
    lactones
  81. cyclic amides
    lactams
Author
lacythecoolest
ID
289224
Card Set
OChem II quiz 3
Description
quiz 3 carbonyl compounds, nomenclature, products, solvents and reactants
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