Chem301 Ch9,10,12 USD

Home > Preview

The flashcards below were created by user Mattyj1388 on FreezingBlue Flashcards.


  1. Addition reactions (page 395)
    • the addition of two groups across a double bond. (In the process, the pi bond is broken).
    • i.e.
    • Image Upload
  2. Some types of addition reactions
    Image Upload
  3. acid-catalyzed hydration (page 406)
    • Addition of water H2O across a double bond in the presence of an acid. [H3O].
    • Image UploadorImage Upload
  4. anti addition (page 425)
    • Addition occures by placing the added compound (or elements) in oppisite directions.
    • Image Upload
  5. anti-Markovnikov addition (page 398)
    When the functional group does not go to the more substituted carbon.
  6. asymmetric hydrogenation (page 422)
    The ability to form one enantiomer rather than two of them.
  7. bromohydrin (page 428)
    BrOH
  8. Bromonium ion (page 427)
    Br -
  9. catalytic hydrogenation (page 418)
    • Involves the addition of moleculare hydrogen (H2) across a double bond in the presence of a metal catalyst; for example:
    • Image Upload
  10. Chlorohydrin (page 428)
    • Cl2 with H2O
    • i.e.
    • Image Upload
  11. dibromane (page 413)
    • It is 2 BH3 molecules sharing 2H.
    • Image Upload
    • Image Upload
  12. dihydroxylation (page 430)
    • (OH)2 added across a alkene.
    • Image Upload
  13. epoxide (page 430)
    • A three membered cyclic ether.
    • Image Upload
    • i.e.
    • Image Upload
  14. halogenation (page 425)
    • Addition of X2 (either Br2 or Cl2) across an alkene.
    • i.e.
    • Image Upload
  15. halohydrin formation (page 428)
    • The process of adding Cl2 with H2O to yeild a Cl and OH substituent
    • i.e.
    • Image Upload
  16. heterogeneous catalysts (page 422)
    • Catalysts that do not dissolve in the reaction medium.
    • i.e. Pt, Pd, Ni
  17. homogeneous catalysts (page 422)
    • Soluable inreaction medium.
    • Called Wilkinson's catalyst
  18. hydration (page 406)
    Adding H2O (to an alkene). or H and OH.
  19. hydroboration-oxidation (page 412)
    • An anti-Markovnikov addition. This process places the OH group at the less substituted carbon:
    • Image Upload
  20. hydrohalogenation (page 397)
    • The treatment of alkenes with HX (where X = Cl, Br, or I) in which H and X are added across the pi bond:
    • Image Upload
    • [The addition of a H and a halogen].
  21. Markovnikov addition (page 398)
    • When performing an addition reaction to an alkene, the Hydrogen (proton) will go to the Carbon that has more Hydrogen, the other half of the addition, (Br, I, Cl, OH, etc) will go to the more substituted carbon.
    • Image Upload

    Image Upload
  22. mercurinium ion (page 411)
    • Is formed when a  pi bond attacks a mercuric cation, the resulting intermediate cannot be considered a carbocation, because the mercury atom has electrons that can interact witht he nearby positive charge to form a bridge. This intermediate, called a mercurinium ion, is more adequately described as a hybrid of two resonance structures. 
    • Image Upload
    • Image Upload
  23. demercuration
    • The process of removing the murcury from the reaction, (is generally accomplished with sodium borohydride (NaBH4). There is much evidence that demercuration occures via a radical process. The net result is the addition of H and a nucleophile across an alkene:
    • Image Upload
    • Many nucleophiles can be used, including water:
    • Image Upload
    • This reaction sequence provides for a two-step process that enables the hydration of an alkene without carbocation rearrangements:
    • Image Upload
  24. Oxonium ion (page 407)
    • An oxygen with a positive charge.
    • i.e.
    • Image Upload
    • or
    • Image Upload
  25. Oxymercuration-demercuration (page 410)
    • A Markovnikov addition without carbocation rearrangements.
    • Image Upload
    • The process begins when mercuric acetate, Hg(OAc)2, dissocciates to form a mercuric cation:
    • Image Upload
    • process:
    • Image Upload
  26. ozonolysis (page 434)
    • The addition of Ozone, O3 with DMS:
    • Image Upload
    • Ozone resonance structure:
    • Image Upload
    • ex:
    • Image Upload
  27. regioselective (page 398)
    When one form of forming a compound is favored over another (like Markovnikov addition).
  28. syn addition (page 413)
    • When addition to an alkene is performed and the both added atoms/compounds are added to the same face.
    • i.e.
    • Image Upload
  29. three-center, two-electron bonds (page 414)
    • Partialy bonded two boron atoms using a total of two electrons.
    • i.e.
    • Image Upload
  30. Weak Nuc  /  Weak Base
    Image Upload
  31. Strong Nuc  /  Strong Base
    Image Upload
  32. Base (only)
    Image Upload
  33. Nucleophile (only)
    Image Upload
  34. How does the concentration of H2SO4 affect addition and/or Elimination reactions?
    Image Upload
  35. Review of reactions
    Image Upload
  36. Acetylide ion (460)
    • The conjugate base of acetylene.
    • Image Upload
  37. alkylation (478)
    • The transformation that proceeds via SN2 reaction and provides a method to install an alkyl group on a terminal alkyne.
    • i.e.
    • Image Upload
  38. alkyne (455)
    A triple bond between carbons. Image Upload
  39. alkynide ion (461)
    • The conjugate base of a terminal alkyl.
    • i.e.
    • Image Upload
  40. dissolving metal reduction (466)
    • Alkynes being reduced to trans alkenes via an entirely different reaction.
    • i.e.
    • Image Upload
  41. enol (471)
    • A double bond (en) and an OH group (ol).
    • i.e.
    • Image Upload
    • The enol cannot be isolated because it is rapidly converted into a ketone.
  42. enolate ion (474)
    • In basic conditions, deprotonation of the enol leads to a resonance-stabalized anion called enolate ion, which is then protonated to generate the aldehyde.
    • i.e.
    • Image Upload
  43. geminal (463)
    • A relationship between to functional groups attached to the same atom.
    • i.e.
    • Image Upload
    • or
    • Image Upload
  44. internal alkynes (458)
    • Disubstituted acetylenes are called internal alkynes.
    • Image Upload
  45. keto-enol tautomerization (472)
    The interconversion between an enol and a ketone.
  46. Poisoned catalyst (465)
    • A partially deactivated catalyst, it is possible to convert an alkyne into a cis alkene (without further reduction):
    • Image Upload
  47. Radical anion (466)
    • In a first step of a mechanism in which a single electron is transferred to the alkyne, generating an intermediate called radical anion:
    • Image Upload
  48. Tautomers (472)
    The enol and ketone are said to be tautomers, which are constitutional isomers that rapidly interconvert via the migration of a proton.
  49. Terminal alkynes (458)
    • Monosubstituted acetylenes
    • Image Upload
  50. Termolecular (469)
    • A substrate (alkyne) reacting with two molecules (HX, X = Br, Cl, I) simultaneously.
    • i.e.
    • Image Upload 
  51. Vicinal (463)
    • Two halogens are connected to adjacent carbon atoms.
    • i.e.
    • Image Upload
    • or
    • Image Upload
  52. Vinylic carbocation (469)
    • An intermediate formed from a mechanism from addition of HX to a triple bond: (1) protonation to form a carbocation followed by (2) nucleophilic attack:
    • i.e.
    • Image Upload
    • vinylic carbocation (vinyl = a carbon atom bearing a double bond) and can successfully explain the observed regioselectiveity.
  53. methylacetylene
    Image Upload
  54. Diisopropylacetylene
    Image Upload
  55. Phenylpropylacetylene
    Image Upload
  56. what is the product from 1-hexeneImage Upload
    • Image Upload
    • because of the peroxide (H2O2)
  57. What are the relative rates of:Image Upload
    • .......................................Rate
    • Image Upload= 1
    • Image Upload= 106
    • Image Upload=1011
  58. Image Upload
    • Both [One charality centrer]
    • Image Upload
  59. Image Upload
    • Both products and always same side attack
    • Image Upload
  60. What are the three things to determine when looking at reaction predictions and synthesis?
    • 1) Determine what type of reaction is required/occuring.
    • ......(i) Substitutions
    • ......(ii) Eliminations
    • ......(iii) Addition reactions
    • 2) Determine conditions to form necessary regiochemical outcome (e.g.):
    • ......(i) Zaitsev or Hofmann products
    • ......(ii) Markovnikov (anti-Markovnikov) addition
    • 3) Determane conditions to form necessary regiochemical outcome (e.g.):
    • ......(i) Stereochemical inversion
    • ......(ii) syn/anti-Addition

    • Be comfertable with changing positions of a:
    • ......(i) Leaving Group: elimination-addition
    • ......(ii) pi-bond: addition-elimination
  61. What is Hydrohalogenation?
    • addition of HX (X=Cl, Br, or I)
    • favors LOW TEMP!
  62. What is Hydration?
    addition of water  or an H & OH
  63. What is Hydrogenation?
    Addition of H2.
  64. what is Halogenation?
    • Addition of X2 (X= Cl or Br)
    • Markovnikov
  65. What is Halohydrin formation?
    Addition of X OH (X = Cl, Br, or I)
  66. What is Dihydroxylation?
    • Addition of (OH)2.
    • Syn-addition and get ananteomers
  67. Image UploadImage Upload
    Image UploadImage Upload
  68. Image UploadImage Upload
    Image UploadImage Upload
  69. Image UploadImage Upload
    Image UploadImage Upload
  70. Image UploadImage Upload
    Image UploadImage Upload
  71. Image Upload
    Image Upload
  72. Image Upload
    Image Upload
  73. Image Upload
    Image Upload
  74. Image Upload
    Image Upload
  75. Image UploadImage Upload
    Image UploadImage Upload
  76. Image UploadImage Upload
    Image UploadImage Upload
  77. Image UploadImage Upload
    Image UploadImage Upload
  78. Image UploadImage Upload
    Image UploadImage Upload
  79. Image Upload
    Image Upload
  80. Image Upload
    Image Upload
  81. Image Upload
    Image Upload
  82. Image UploadImage Upload
    Image UploadImage Upload
  83. Image UploadImage Upload
    Image UploadImage Upload
  84. Image Upload
    Image Upload
  85. Image Upload
    Image Upload
  86. Image Upload
    Image Upload
  87. Image Upload
    Image Upload
  88. Image Upload
    Image Upload
  89. We want to make an alkyne, so what reactions do we know that can be used to make an alkyne?
    Image Upload
    Image Upload

Card Set Information

Author:
Mattyj1388
ID:
186151
Filename:
Chem301 Ch9,10,12 USD
Updated:
2012-12-15 09:16:05
Tags:
Ch9 ch10 ch12 Organic Chem 301 USD chapters parts
Folders:

Description:
general terms and definitions text book "Organic Chemistry" University of San Diego/ Klein: copyright 2012 John Wiley & Sons, Inc. arrow pushing, carbocations,addition reactions, alkynes, radical reactions.
Show Answers:

Home > Flashcards > Print Preview