Reagents2

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albrow10
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Reagents2
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2013-10-03 22:50:42
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Reagents
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  1. Sn1-Substitution of a halide with a nucleophile on a 3o and sometimes a 2o substrate. Gives two products if there is a chiral center because of racemization.
    Reagent is a weak nucleophile and is usually a ROH or HOH.  The reagent is usually the solvent, but the solvent should be a polar protic (polar and has H-bonding).
  2. Sn2-Substitution of a halide with a nucleophile on a 1o and sometimes a 2o substrate.  Inverts the chiral center.
    Needs a strong Nu so it is usually negative (usually part of a salt with Na is most popular).  It can't be a bulky reagent.  The solvent should be polar aprotic (polar but doesn't have H-bonding).  Common solvents are DMSO or acetone.
  3. E1-Elimination where the halide and a H are eliminated to form a double bond.  Rearrangements are possible.  It looks like this isn't really used a whole lot.
    Weak bases like ROH or HOH.  Solvent is polar protic and is usually just the reagent.
  4. E2-Elimination of a halide and a H to form an alkene.  Only can be formed if LG and H are staggered.  This means it forms a trans alkene. With 3o substituent there is no competition with Sn2 , but with 2o and 1o there is competition.
    Strong bases are used.  Solvents are polar and can be aprotic or protic.  So unlike with Sn2 H2O and ROH can be used.  Small bases like NaOH used to create most subst. alkene whereas bulky bases like NaOtBu (used with solvent of HOtBu) create the least subst. alkene (in 3o, but in 2o and 1o it is always the most?).
  5. Add a H and halide (Br for example).  Rearrangement is possible and the stereocenters are racemized. Markovnikov for the halide.
    The reagents are only HBr or HCl.
  6. H and OH are added with rearrangements possible and racemization occurring at the stereocenter. OH is added markovnikov.
    Reagents are H2O with an acid catalyst (like H2SO4)
  7. H and OR are added with rearrangements possible and racemization occurring at the stereocenter.  OR is added markovnikov.
    Reagents are ROH with and acid catalyst (like H2SO4).
  8. Two Br's or Cl's are added in anti addition.
    Br2 or Cl2 in CH2Cl2
  9. Addition of Br or Cl and OH with anti addition and markovnikov of OH on most subst.
    Br2 or Cl2 with H2O
  10. Addition of Br or Cl and OR with anti addition and markovnikov of OH on most subst.
    Br2 or Cl2 with ROH
  11. H and OH are added without rearrangements possible and without racemization, but rather added in anti addition. The OH is added markovnikov.
    • 1. Hg(OAc)2, H20/THF
    • 2. NaBH4
  12. H and OR are added without rearrangements  possible and without racemization, but rather in anti addition.  The OR is added markovnikov.
    • 1. Hg(OAc)2, ROH
    • 2. NaBH4
  13. H and OH are added in syn addition and with anti-markovnikov of the OH.
    • 1. BH3/THF
    • 2. H2O2, H2O, NaOH
  14. 2 H's are added in syn addition.
    H2, Pd/C
  15. Addition of a Br to an alkane (this is actually a substitution b/c it's taking the place of a H).  Important because adding a functional group from just an alkane.  The Br adds to the most substituted.
    Br2 with hv
  16. Adds a Br to the sp3 C next to the sp2 C of an alkene.
    NBS, hv or heat, peroxide (H2O2,
  17. Adds H and Br in anti-markovnikov addition.
    HBr and peroxide (H2O2, Et2O2, etc.)
  18. Addition of 2 H's and 2 Br's or Cl's to an alkyne with Markovnikov of Br for both.
    2 eq of HBr or HCl
  19. Adding two Br's or Cl's to each side of an alkyne.
    2 eq of Br2 or Cl2 in CH2Cl2
  20. Addition of two H's on least subst. side of alkyne with double bonded O on most subst. side.
    1 eq. of H2O with H2SO4, HgSO4
  21. Addition of two H's on most subst. side of alkyne with double bonded O on most subst. side.
    • 1. disiamyborane
    • 2. H2O2, OH
  22. Reaction that makes a terminal alkyne a very important basic acetylide ion.  The acetylide ion can then react with compounds that have a LG that just left.
    NaNH2
  23. Reduces double and triple bonds completely to alkanes by adding H's.
    H2, Pd/C
  24. Reduces triple bonds to double bonds with syn addition of H's.
    H2, Lindlar's Catalyst
  25. Reduces triple bonds to double bonds with trans addition of two H's.
    Na0NH3(l)
  26. Takes a Br off of an alkane and adds an H in it's spot. Second step is used to quench or neutralize the ions.
    • 1. LiAlH4
    • 2. H2O
  27. In a three-membered ring with an O this reagent takes a bond away breaking the ring apart and then the O is protonated.
    • 1. LiAlH4
    • 2. H2O
  28. Add a three-membered ring with O.  Syn addition as adding to either top or bottom.  Makes enantiomers if that is done to both.  Good way to add O.
    mCPBA
  29. With an epoxide this reagent adds an OH to both sides forming a trans product.
    • 1. NaOH, H2O
    • 2. H3O+
    • or just H3O+
  30. With an alkene this reagent adds an OH to both sides forming a cis product.
    • 1. OsO4
    • 2. NaHSO4, H2O
    • or KMnO4, H2O, NaOH
  31. Breaks the double bonds (need to ask question of if it's just double bonds or if it's triple bonds as well???) and then adds double bonded O to both places to fill the break.
    • 1. O3 at -78o C
    • 2. Zn, H2O
  32. When there are three C's and the middle one is attached to an O this reagent and this reagent makes a ketone.
    • PCC (weak reagent)
    • or CrO3, H2SO4
  33. When there are two C's and one is attached to an O this reagent makes an aldehyde.
    PCC (the weak one)
  34. When there are two C's and one is attached to an O this reagent makes a carboxylic acid.
    CrO3, H2SO4 (the strong one)
  35. Substituting OH for I on a primary carbon.
    HI and the reaction is Sn2
  36. Substituting OH for I on a secondary carbon.
    HI and the reaction is Sn1
  37. Substituting OH for I on a tertiary carbon.
    HI and the reaction is Sn1
  38. Substitution of OH for Br on a primary carbon.
    HBr and the reaction is Sn2
  39. Substitution of OH for Br on a secondary carbon.
    HBr and the reaction is Sn1
  40. Substitution of OH for Br on a tertiary carbon.
    HBr and the reaction is Sn1
  41. Substitution of OH for Cl on a primary carbon
    HCl, ZnCl2 and the reaction is Sn2
  42. Substitution of OH for Cl on a secondary carbon.
    HCl, ZnCl2 and reaction is Sn1
  43. Substitution of OH for Cl on tertiary C.
    HCl, ZnCl2 and reaction is Sn1
  44. Substitution of OH for Br on primary C with bulky base.
    PBr3, pyridine and reaction is Sn2
  45. Substitution of OH for Br on secondary C with bulky base.
    PBr3, pyridine and reaction is Sn2
  46. Substitution of OH for Cl on primary C with bulky base.
    SOCl2, pyridine and reaction is Sn2
  47. Substitution of OH for Cl on secondary C with bulky base.
    SoCl2, pyridine and reaction is Sn2
  48. The reagent that is used when the nucleophile is a strong base (not a halide) in a substitution reaction when OH (essentially water) is the LG.
    • 1. TsCl, MsCl, or TfCl all with pyridine. 
    • 2. Nu- (that is strong base as well as good nucleophile.
  49. E1 reaction with OH as LG.  Secondary and tertiary are preferred.  Gives rearrangement. Always gives most subst. alkene.
    H2SO4, H2O, heat
  50. E2 reaction with OH as LG.  Primary is preferred, but can do all three.  For primary it gives most subst. alkene but for secondary and tertiary it gives least subst. alkene.
    • POCl3, pyridine
    • In this mechanism pyridine deprotonates C on other side of alkene while the LG is leaving.  It's a concerted step.
  51. Substitution involving an ether.  The mechanism looks like it ends up being first Sn2 and then Sn1.  That means there are multiple products formed. Both sides of the ether have to be sp3 hybridized or it won't split. Just split on either side of O and add the halide.
    HX where X is a halide.  HI>HBr>>HCl
  52. Epoxide ring opening in basic conditions.  It's Sn2 and so the OH and the Nu- add on with the Nu- on the least subst. C.
    • 1. Nu-,
    • 2. H3O+
  53. Epoxide ring opening in acidic conditions.  It's Sn1 and so the OH and the Nu add on with the Nu on the most subst. because of the carbocation in the resonance structure.
    Nu, acid catalyst add on at the same time.
  54. Oxidizing any non 4o alkane side chain of a benzene to carboxylic acid. 1 CO2 goes for every C after the initial C of the chain that there is.
    • 1. KMnO4, heat
    • 2. H3O+
  55. Reducing O2N benzene side chain to H2N in a not selective way, meaning all double bonds will be reduced.
    2 eq of H2, Pd/C
  56. Reducing O2N benzene side chain to H2N.  It's very selective and happens in two steps.
    • 1. Sn (or Fe), HCl
    • 2. NaOH
  57. Take away the carbonyl group on any alkane side chain of benzene.
    H2NNH2, OH-, heat
  58. NO2 is added to benzene ring.
    HNO3, H2SO4
  59. SO3H is added to benzene ring
    SO3, H2SO4
  60. Cl is added to benzene ring
    Cl2 with catalyst AlCl3
  61. Br is added to benzene ring
    Br2 with catalyst of FeBr3
  62. I is added to benzene ring
    I2 with catalyst of HNO3
  63. R is added to benzene ring
    RX with catalyst of AlCl3
  64. O=CR is added to a benzene ring
    RCOCl with catalyst of AlCl3
  65. O=CH is added to a benzene ring
    CO, HCl with catalyst of AlCl3

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