OChem 2- Week 1

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chiroclown
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35327
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OChem 2- Week 1
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2010-09-17 20:20:10
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OChem 2- Week 1
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  1. Halo Alkanes Naming
    • Don't have their own name ending- No Respect
    • 1-Chloro-Propane, etc.
  2. Alky Halides
    • BP increases 20-30 degrees fro every carbon added
    • Density is greater than water- Sinks
    • Weigh alot
  3. Boiling Point is Directly related to
    • Shape
    • Hydrogen Bonding
    • Polarity
    • Molecular Weight
  4. Hydrogen bonded to FON
    Able to form hydrogen bonds with self and has inordinatel high BP
  5. Synthesis of Alkyl Halides
    • SHEA
    • Substitution
    • Halogenation
    • Exchange
    • Addition
  6. Substitution
    • Synthesis
    • Someone steps up, someone steps down
    • R-OH------> (HX)--------> R-X + H2O
  7. Cleavage of PCl3 in substitution
    PCl2+ and Cl-
  8. Cleavage of Iodine in Substitution
    I+ and I-
  9. nI2x
    • No I2 with X
    • Iodine is always a problem because it is so large
  10. *** Remember- the reaction of 1 family is synthesis of another family
  11. Exchange of Halide
    • Synthesis
    • R-X + Na+ I- -----> (Acetone) -------> R-I + Na+X-
  12. **** Remember- Carbons w/ Halogen is partially positive and Halogen is partially negative
  13. Halogenation of Halo Alkanes
    • Synthesis
    • Sayetzef- Poor get poorer (Major), Rich get poorer (Minor)
    • Major will create 2o Carbocation/ Free Radical
    • Minor will create 1o Carbocation/ Free Radical
  14. Addition of Hydrogen Halides to Alkenes
    • Synthesis
    • nI2x
    • -C=C- -------> C-C with X on the C-C
    • Alkene to Alkane
  15. Reactions of Alkyl Halides
    North South G-R-i-D

    • Nucleophilic
    • Substitution

    • Grignard Reagent
    • Reduction of Metal by an Acid
    • Dehydrohalogenation
  16. Nucleophile
    • Negatively charged atom/ molecule
    • I am negative, I love positive
  17. Grignard Reagent
    • Reaction
    • Provides an R- group
    • R-X + Mg ---------> (Dry Ether) ---------> RMgX
  18. Reduction by a Metal and Acid
    • Reaction
    • R-X + Zn + HX ------> R-H + ZnX
  19. Dehydrohalogenation of Alkyl Halides
    • Reaction
    • Sayetzef- Poor get Poorer (Major), Rich get Poorer (Minor)
    • -C-C- (with one X on one C) -------> (Base) ---------> -C=C-
    • Alkane to Alkene
  20. Oxidation
    • Gain of Oxygen
    • Loss of Hydrogen
    • Loss of Electron
  21. Reduction
    • Loss of Oxygen
    • Gain of Hydrogen
    • Gain of Electron
  22. Nucleophiles are...
    • 1) Groups with Negative Charges
    • OH-, O-R-, -C(triple bond)C-R, I-, C(triple bond)N-, -SH, -S-R
    • 2) Lone Pairs/ unshared pair of electrons (i.e, :NH3)
    • 3) Groups so polarized as to almost be with a negative charge
  23. Nucleophilic Subsitution
    Sn1 an Sn2
  24. Sn1
    • 1) First order kinetics
    • 2) Racemization
    • 3) Rearrangement (Carbocation Mediated)
    • 4) Has 3o Alkyl Halides Reaction

    * 2 Steps
  25. Sn2
    • 1) Second order Kinetics
    • 2) Complete Stereochemical Inversion
    • 3) Absense of Rearragement (NOT carbocation mediated
    • 4) 1o alkly halides react fastest

    *One Step
  26. Alcohols
    • BP increases by 20-30 degrees for each carbon added
    • Density is less than 1
    • Most alchols float
    • Aromatic Rings, Diols and Triols Don't float- greater than 1
  27. Benzen Rings Side Group
    Phenyl
  28. Solubility
    g/ 100g of H2O
  29. Dipel Moment
    The greater the #, the more polar the molecule
  30. Synthesis of Alcohols (8 kinds)
    • Oxymercuration-Demurcuration
    • Hydroboration-Oxidation
    • Grignard Synthesis
    • Hydrolysis of Alkyl Halides
    • Aldol Condensation
    • Reduction of Carbonyl Compounds
    • Reduction of Acids and Esters
    • Hydroxylation of Alkenes
  31. Reactions of Alcohols (6 kinds)
    • Reaction of Hydrogen Halides
    • Reaction with phosphorus Trihalides
    • Dehydration
    • Reaction as acids: reaction with active metals
    • Ester Formation
    • Oxidation
  32. Oxymercuration- demurcuration of OH
    • Synthesis
    • Markovnikov- Major only, Rich get Richer
    • -C=C- + Hg(OAc)2 + H2O ------> CH2(OH)CH2(HgOAc) ------> (NaBH4) -------> CH2(OH)-CH3
    • Alkene to Alkane
  33. Hydration of Alcohols
    • Synthesis
    • Markovnikov- Major (2o)/ Minor (1o)
    • Alkene to Alkane
    • -C=C- + H2O ------> -C-C-OH
    • Alkene to Alkane
  34. Hydroboration-Oxidation of Alcohol
    • Synthesis
    • Minor Only- Rich still gets Richer
    • No carbocation rearrangement
    • -C=C- + (BH3)2 ------> CH3CH2(B) ------> (H2O2 OH-) -------> CH3CH2(OH) + B(OH)3
  35. BAA
    • Benzylic
    • Allylic
    • Alpha
  36. Benzylic Carbon
    • Carbon NEXT TO the carbon participating in the benzene ring
    • Easiest to remove
    • C-Benzene Ring
  37. Alpha Carbon
    • Carbon nexty to carbonyl carbon
    • Easiest to remove
    • C-C-C(O)
  38. Allylic Carbon
    • Carbon next to carbon participating in double bond
    • Easiest to remove
    • C-C=C
  39. Formaldehyde in Grignard Synthesis
  40. 1o Alcohol
  41. Higher Aldehydes in Grignard Synthesis
    2o Alcohol
  42. Ketones
    3o Alcohol
  43. Apoxide/ Ethylene Oxide in Grignard Synthesis
    1o Alcoho with 2 carbons added
  44. Ester in Grignard Synthesis
    3o alcohol
  45. Hydrolysis of Alkyl Halides
    R-X + OH (or H2O) --------> R-OH + X (or HX)
  46. Hydroxy
    Naming for alcohol when alcohol is not determined to be the functional group
  47. Aldol
    Alcholy and Aldahide
  48. Aldol Condensation
    • Aldehyde + Aldehyde + Base = Aldol
    • Base removes an alpha H
    • Electrons in second aldehyde hanging out looking for a home
    • second aldehyde attachs carbonyl carbon
    • Creates an Aldol (alcohol and aldeyde)
  49. Reduction of Carbonyl Compounds
    • Creation of alcohol by reduction (GAIN OF H)
    • R-C(O)(OH) + 2Li+ AlH4- + 2H+Cl-------> R-CH2(OH) + H20
    • Oxygen attaches to a H and creates OH
    • Original OH attaches to H and creates H20
  50. Carbocylic Acids
    R-C(O)(OH)
  51. Aldehyde
    R-CH(O)
  52. Ketone
    R-C(O)-R
  53. Esther
    R-C(O)(O)R
  54. Hydroxylation of Alkenes
    • KMnO4, Cold, Dil
    • Major and Minor creates Diol
    • -C=C- -----> -C-C- Diol
  55. Reactions of Alcohols (6 Kinds)
    • Reaction with hydrogen halides
    • REaction with phosporus trihalides
    • Dehydration
    • Reaction as acids: Reaction iwth active metals
    • Ester Formation
    • Oxidation
  56. Reaction with Hydrogen Halides
    • R-OH + HX --------> R-X + H2O
    • Double check for Hydride shift in the R group
  57. Reactivity of ROH
    Allyl, Benzyl > 3o > 2o > 1o
  58. Reaction with phosporus trihalides
    3R- OH + PX3 ------> 3R-X + H3PO3
  59. Dehydration
    • Syetzef- Poor get Poorer (Major), Rich get Poorer (Minor)
    • Hydride shift may occur
    • -CH2-CH2(OH)- --------> (Acid) -------> -Ch2=CH2- + H2O
    • Alkane to Alkene
  60. Reactions as Acids: Reaction with Active Metals
    • Basis of Breathalizer
    • RO-H + M --------> RO-M+ + H
  61. Esther Drinks Coors
    R-C(O)(O)R
  62. O-ate the Can
    Butanoate
  63. Ethanol + Butanoic Acid
    Ethyl Butanoate
  64. Carbonyl Carbon
    Partially positive carbon
  65. Ester Formation
    Hidden in the thame of ester, you will find the reagent.
  66. Oxidation of Alcohol- 1o alcohol
    • Has Major/ Minor
    • Major creates an aldehyde
    • Minor creates a carboxylic Acid (Reacting with KMnO4)
  67. Oxidation of Alcohol- 2o Alcohol
    • Creates a Ketone
    • Reacting with K2Cr2O3 or CrO3
  68. Aldehyde
    R-CH(O)
  69. Carboxylic Acid
    R-C(O)(OH)
  70. Ketones
    R-C(O)-R
  71. Oxidation of Alchol- 3o Alcohol
    NO REACTION
  72. ID of Alcohols
    • CLIP
    • Chromic Anhydride in Sulfuric Acid- Jone's Reagent
    • Lucas Test
    • Iodoform Test
    • Periodic Acid Test
  73. Chromic Anhydride in Sulfuric Acid- Jone's Reagent
    1o alcohol in CrO3 + H2SO4 ------> Aldehyde (Blue Green)

    2o alcohol in CrO3 + H2SO4 -------> Ketone (Blue Green)

    3o alcohol in CrO3 + H2SO4 --------> NO REACTION

    When a primary or secondary alcohol is added to clear orange chromic in anhydride the solution becomes opque and Blue-Green
  74. Lucas Test
    R-OH + HCl + ZnCl2 -------> Cloudiness R-Cl + H2O

    3o reacts instantly

    2o reacts within 5 minutes

    1o WILL NOT REACT
  75. Iodoform Test
    • Reacts with METHYL ALCOHOLS
    • Tests for Iodine
    • R-CH(OH)-CH3 + 3NaOI -------> R-CH(O) + CH(I3)
    • Creates Yellow Precipitate
  76. Periodic Acid Test
    • Tests for Vicinal Diols
    • Non Vicinal = NO REACTION
    • R-CH(OH)-CH(OH)-R + HIO4 -------> R-C(O)-H + R-C(O)-H + HIO3

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