O-chm reagents

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albrow10
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233162
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O-chm reagents
Updated:
2013-09-06 23:38:57
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reagents
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reagents
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  1. What does the reagent H2 do with a catalyst of Pt/C Pd/C or Ni? (alkene)
    • Adds two H's to an alkene and makes it an alkane.
    • Syn-addition
  2. What does the reagent HBr or HCl do? (alkene)
    • It adds H and Br/Cl to an alkene and makes it an alkane.
    • Markovnikov (Br/Cl to the most substituted).
    • Rearrangement is possible.
    • Random Racemization.
  3. X2, CH2Cl2 (alkene)
    • Adds to X's to an alkene to make it an alkane.
    • Anti-addition
  4. X2, H2O (alkene)
    • X and OH are added to an alkene and makes it alkane.
    • Markovnikov (OH added to most subst.)
    • Anti-addition
  5. X2, ROH (alkene)
    • Adds X and OR to an alkene making it an alkane.
    • Markovnikov (OR added to most subst.)
    • Anti-addition
  6. Br2, NaCl (alkene)
    • Br and Cl are added to an alkene making it an alkane.
    • Markovnikov (Cl on most subst.)
    • Anti-addition
  7. H2O, Acid Catalyst (alkene)
    • H and OH are added to an alkene making it an alkane.
    • Markovnikov
    • Rearrangement is possible.
    • Random/racemization
  8. 1.Hg(OAc)2, H2O/THF (alkene)
    2. NaBH4
    • H and OH are added to an alkene making it an alkane
    • Markovnikov
    • Anti-addition
  9. 1. BH3, THF (alkene)
    2. H2O2, H2O, NaOH
    • H and OH are added to an alkene making it an alkane.
    • Anti-Markovnikov
    • Syn-addition
  10. ROH with Acid  (alkene)
    • H and OR are added to an alkene making it an alkane.
    • Markovnikov
    • Rearrangement possible
    • Random/racemization
  11. 1. Hg(OAc)2, ROH (alkene)
    2. NaBH4
    • H and OR and added to an alkene making it an alkane.
    • Markovnikov
    • Anti-addition
  12. 2 eq. of HBr or HCl (alkyne)
    Adds two Br or Cl to most subst. and two H's to least subst. of the alkyne bond.
  13. 2 eq. of Br2 or Cl2 (alkyne)
    Adds two Br or Cl to each side.  In the intermediate they are added to make a trans product.
  14. 1 eq. of H2O and an acid catalyst (alkyne)
    Has two steps.  The first step uses the eq. of H2O and makes an enol, adding an OH to the most subst. and an H to the least subst.  and reducing the alkyne to an alkene.  The second step is spontaneous and adds a H to the least subst. side, reduces the alkene to an alkane, and makes the bond to an O a double bond and takes away the H connected to the O.
  15. H2O, H2SO4, HgSO4 (alkyne)
    • Alternate form of converting alkyne to enol and then to keto.
    • So essentially alkyne is taken and becomes an alkane with two H's on least subst. side and a double bonded O on the most subst. side.
  16. 1. Disiamyborane (alkyne)
    2. H2O2, OH-
    • The anti-mark version of the alkyne to Enol to Keto mechanism.
    • Alkyne is taken and becomes an alkane with two H's on most subst. end and double bonded O on least subst. end.
  17. H2, Pd/C (alkyne)
    reduces double and triple bonds completely to alkanes (giving H's in place of pi bonds)
  18. H2, Lindlar's Catalyst (alkyne)
    Reduces triple bonds to double bonds with syn addition of two H's.
  19. Na/NH3 (alkyne)
    Reduces triple bonds to double bonds with trans addition of two H's.
  20. NaNH2
    • This is a very important one. 
    • It is used to deprotonate an alkyne and turn it into a strong Nucleophile.
  21. MCPBA
    Adds O to where alkene used to be and alkane now is as a three-membered ring.
  22. What are common bases used for E1 reactions?
    H2O, ROH
  23. What are common bases used in E2 reactions?
    • Small bases (to be on most subst.) - OH-, CH3O-
    • Bulky bases (to be on least subst.)- HOtBu, DBN, DBU
  24. What are common solvents for SN1?
    Weak Nucleophiles-CH3OH (any ROH), H2O, etc.
  25. What are common solvents for SN2?
    Strong nucleophiles- NaNwith DMSO, NaOH with water, etc.
  26. Br2 or Cl2 and hv (light) (alkane)
    Addition of Br to alkane at most subst. and Cl to either.
  27. NBS with light/heat and peroxide (H2O2) (alkene)
    Adds Br to C next to the alkene
  28. HBr and peroxide (H2O2, R2O2, ROOR) (alkene)
    Adds Br to least substituted and changes alkene to alkane.
  29. NaNH2
    Strong base that is used to deprotonate an alkyne.
  30. Nao, NH3
    • Reduces a triple bond to double bond.
    • Adds H's to make trans alkene
  31. 1. LiAlH4
    2. H2O
    Takes leaving group off and is replaced with H or bond moves somewhere else on Molecule.
  32. What are some reagents for oxidation?
    • PCC-weak
    • CrO3, H2SO4

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