Chem301 Ch9,10,12 USD

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Chem301 Ch9,10,12 USD
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2012-12-15 04:16:05
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Ch9 ch10 ch12 Organic Chem 301 USD chapters parts
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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.
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  1. Addition reactions (page 395)
    • the addition of two groups across a double bond. (In the process, the pi bond is broken).
    • i.e.
  2. Some types of addition reactions
  3. acid-catalyzed hydration (page 406)
    • Addition of water H2O across a double bond in the presence of an acid. [H3O].
    • or
  4. anti addition (page 425)
    • Addition occures by placing the added compound (or elements) in oppisite directions.
  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:
  10. Chlorohydrin (page 428)
    • Cl2 with H2O
    • i.e.
  11. dibromane (page 413)
    • It is 2 BH3 molecules sharing 2H.
  12. dihydroxylation (page 430)
    • (OH)2 added across a alkene.
  13. epoxide (page 430)
    • A three membered cyclic ether.
    • i.e.
  14. halogenation (page 425)
    • Addition of X2 (either Br2 or Cl2) across an alkene.
    • i.e.
  15. halohydrin formation (page 428)
    • The process of adding Cl2 with H2O to yeild a Cl and OH substituent
    • i.e.
  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:
  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:
    • [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.

  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. 
  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:
    • Many nucleophiles can be used, including water:
    • This reaction sequence provides for a two-step process that enables the hydration of an alkene without carbocation rearrangements:
  24. Oxonium ion (page 407)
    • An oxygen with a positive charge.
    • i.e.
    • or
  25. Oxymercuration-demercuration (page 410)
    • A Markovnikov addition without carbocation rearrangements.
    • The process begins when mercuric acetate, Hg(OAc)2, dissocciates to form a mercuric cation:
    • process:
  26. ozonolysis (page 434)
    • The addition of Ozone, O3 with DMS:
    • Ozone resonance structure:
    • ex:
  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.
  29. three-center, two-electron bonds (page 414)
    • Partialy bonded two boron atoms using a total of two electrons.
    • i.e.
  30. Weak Nuc  /  Weak Base
  31. Strong Nuc  /  Strong Base
  32. Base (only)
  33. Nucleophile (only)
  34. How does the concentration of H2SO4 affect addition and/or Elimination reactions?
  35. Review of reactions
  36. Acetylide ion (460)
    • The conjugate base of acetylene.
  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.
  38. alkyne (455)
    A triple bond between carbons.
  39. alkynide ion (461)
    • The conjugate base of a terminal alkyl.
    • i.e.
  40. dissolving metal reduction (466)
    • Alkynes being reduced to trans alkenes via an entirely different reaction.
    • i.e.
  41. enol (471)
    • A double bond (en) and an OH group (ol).
    • i.e.
    • 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.
  43. geminal (463)
    • A relationship between to functional groups attached to the same atom.
    • i.e.
    • or
  44. internal alkynes (458)
    • Disubstituted acetylenes are called internal alkynes.
  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):
  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:
  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
  50. Termolecular (469)
    • A substrate (alkyne) reacting with two molecules (HX, X = Br, Cl, I) simultaneously.
    • i.e.
    •  
  51. Vicinal (463)
    • Two halogens are connected to adjacent carbon atoms.
    • i.e.
    • or
  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.
    • vinylic carbocation (vinyl = a carbon atom bearing a double bond) and can successfully explain the observed regioselectiveity.
  53. methylacetylene
  54. Diisopropylacetylene
  55. Phenylpropylacetylene
  56. what is the product from 1-hexene
    • because of the peroxide (H2O2)
  57. What are the relative rates of:
    • .......................................Rate
    • = 1
    • = 106
    • =1011
    • Both [One charality centrer]
    • Both products and always same side attack
  58. 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
  59. What is Hydrohalogenation?
    • addition of HX (X=Cl, Br, or I)
    • favors LOW TEMP!
  60. What is Hydration?
    addition of water  or an H & OH
  61. What is Hydrogenation?
    Addition of H2.
  62. what is Halogenation?
    • Addition of X2 (X= Cl or Br)
    • Markovnikov
  63. What is Halohydrin formation?
    Addition of X OH (X = Cl, Br, or I)
  64. What is Dihydroxylation?
    • Addition of (OH)2.
    • Syn-addition and get ananteomers
  65. We want to make an alkyne, so what reactions do we know that can be used to make an alkyne?

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