Orgo Reagents and Functional Groups

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Author:
Charlie581
ID:
300997
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Orgo Reagents and Functional Groups
Updated:
2015-05-04 23:24:13
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Reagents Functional Groups
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Description:
Orgo Reagents (for Addition, Alkyne, and Alcohol chemistry) and a few Functional Groups
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  1. If you are starting with an alkene, and wanted to end with Br in the least substituted position?
    HBr/ROOR
  2. If you are starting with an alkene, and wanted to end with Br in the most substituted postition?
    HBr
  3. If you are starting with an alkene, and wanted to end with syn addition of (2) OH groups?
    OsO4/NMO
  4. If you are starting with an alkene, and wanted to end with anti addition of 2 OH groups?
    • 1) RCO3H
    • 2) H3O+
  5. If you are starting with an alkene, and wanted to end with OH in the most substituted position and Br in the least substituted position?
    Br2, H2O
  6. If you are starting with an alkene, and wanted to end with anti addition or 2 Br groups?
    Br2
  7. If you are starting with an alkene, and wanted to end with and alkane?
    H2 / Pt
  8. If you are starting with an alkene, and wanted to end with OH in the least substituted position?
    • 1) BH3 - THF
    • 2) H2O2, NaOH
  9. If you are starting with an alkene, and wanted to end with OH in the most substituted position?
    H3O+
  10. If you are starting with an alkene, and wanted to end with OH in the most substituted position while avoiding any carbotation rearrangement?
    • 1) Hg(OAc)2, H2O
    • 2) NaBH4
  11. If you are starting with an alkane, and wanted to end with Br in the most substituted position?
    Br2 / Δ
  12. If you are starting with an alkane with X in the most substituted position, and wanted to end with and alkene?
    NaOEt
  13. If you are starting with either a vicinal or geminal dibromide (or dihalide), and wanted to end with an alkyne?
    • 1) xs NaNH2
    • 2) H2O
  14. If you are starting with an alkyne, and wanted to get Bromine (or other halide) in the most substituted position, and then get an a geminal dihalide?
    You would use 2 equivalent of HBr (one to get the Br in the most substituted position of a now alkene, and another to turn that into a geminal dihalide alkane)
  15. If you are starting with a terminal alkyne, and wanted to end with a ketone?
    • H2SO4, H2O / HgSO4
    • Note: This reaction will first undergo markovnikov addition of H and OH to give an enol, but it will quickly tautomerize to form the ketone
  16. If you are starting with a terminal alkyne, and wanted to end with an aldehyde?
    • 1) R2BH (or 9-BBN)
    • 2) H2O2, NaOH

    Note: This reaction will first undergo anti-markovnikov addition of H and OH to give an enol, but it will quickly tautomerize to form the aldehyde
  17. If you are starting with a terminal alkyne, and wanted to end with a trans halogenated alkene?
    one equivalent of Br2
  18. If you are starting with a terminal alkyne, and wanted to end with a tetrahalide (2 X's added to each spot)?
    excess equivalent of X2 (such as Bromide)
  19. If you are starting with a terminal alkyne, and wanted to end with an internal alkyne?
    • 1) NaNH2
    • 2) RX (such as CH3I)
  20. If you are starting with an internal alkyne, and wanted to end with a cis-alkene?
    H2 / Lindlars' Catalyst
  21. If you are starting with an internal alkyne, and wanted to end with an alkane?
    H2 / Pt
  22. If you are starting with an internal alkyne, and wanted to end with a trans-alkene?
    Na / NH3(liq)
  23. What reagent(s) could be used to achieve the following?

    OH → RO(alkoxide ion)
    • 1) NaH
    • 2) H 

    Both may cause deprotonation of the alcohol, liberating hydrogen
  24. What can the following reagent(s) reduce? What can it not reduce (if any)?

    NaBH4, MeOH
    NaBH4, MeOH is a weak reducing agent, thus it may reduce the following...

    • Ketone → OH
    • Aldehyde → OH

    It is unable to reduce esters or carboxylic acids
  25. What can the following reagent(s) reduce? What can it not reduce (if any)?

    1) LAH
    2) H2O
    LAH is a strong reducing agent, and may reduce the following...

    • Ketone → OH
    • Aldehyde → OH
    • Ester → OH
    • Carboxylic Acid → OH
  26. What can the following reagent(s) reduce? What can it not reduce (if any)?

    H2, Pt
    H2, Pt is a weak reducing agent, and can only reduce the following:

    • Alkene → Alkane
    • Ketone → OH
  27. What may the following reagent(s) react with, and what may it produce?

    Mg
    Mg can be used to convert an alkyl halide into a Grignard reagent 

    RX + Mg → RMgX
  28. What may the following reagent(s) react with, and what may it produce?

    RMgX
    RMgX is a Grignard reagent (examples include MeMgBr, EtMgBr, and PhMgBr, etc...). They are very strong nucleophiles (and thus may also act as very strong bases). They may react with the following:

    • Ketone → 3o OH
    • Ester (when treated with xs grignard) → 3o OH
    • Aldehyde → 2o OH
    • Formaldehyde → 1o OH
  29. What reagent would you use to protect an alcohol?
    Trimethylsilyl chloride (TMSCL), in the presence of a base (such as trimenthylamine Et3N)
  30. What reagent would you use to deprotect an alcohol?
    Tetrabutyl ammonium floride (TBAF)
  31. What may the following reagent(s) react with, and what may it produce? (with respect to alcohols)

    HX
    Hydrogen halides (such as HBr or HCl) are strong acids and also a source of a strong nucleophile which may be used to convert an alcohol to an alkyl halide 

    HX + ROH → RX
  32. What may the following reagent(s) react with, and what may it produce? (with respect to alcohols)

    PBr3
    • 1o OH → RBr (Alkyl bromide)
    • 2OH → RBr (Alkyl bromide)

    • If the OH group is connected to a chirality center, we expect inversion of configuration via SN2 mechanism 
  33. What may the following reagent(s) react with, and what may it produce? (with respect to alcohols)

    SOCl2, pyridine
    • 1o OH → RCl (Alkyl chloride)
    • 2o OH → RCl (Alkyl chloride)

    If the OH group is connected to a chirality center, we expect inversion of configuration via SN2 mechanism
  34. What may the following reagent(s) react with, and what may it produce? 

    HCl, ZnCl2
    OH → RCl (alkyl chloride)
  35. What can the following reagent(s) oxidize? What can it not reduce (if any)?

    Na2Cr2O7, H2SO4, H2O
    A mixture of sodium dichromate (Na2Cr2O7) and sulfuric acid (H2SO4) gives chromic acid, which is a strong oxidizing agent, and may oxidize the following:

    • 1o → Carboxylic acid
    • 2o → Ketone

    Chromic acid does not react with 3o alcohols, as they are generally unreactive
  36. What can the following reagent(s) oxidize? What can it not reduce (if any)? 

    PCC, Ch2Cl2
    PCC, Ch2Cl2 is a weak oxidizing agent, and may oxidize the following:

    • 1o → Aldehyde 
    • 2o → Ketone
  37. What does an Ester look like?
  38. What does an Ether look like?
  39. What does Acetone look like?
  40. What does an Aldehyde look like?
  41. What does Formaldehyde look like?
  42. What does Carboxylic Acid look like?
  43. What does an Amide look like?
  44. What reagent would you use to go from an alkene to an epoxide?
    MCPBA
  45. What reagent would you use to add Bromine in the most substitution position on an alkane?
    Br2 / heat
  46. What reagent would you use to add Bromine in the allylic position on an alkene?
    NBS / hv
  47. Consider the following complex substituents...

    1) Isopropyl
    2) Isobutyl
    3) Sec-butyl
    4) Tert-butyl
    5) Isopentyl
    6) Sec-pentyl

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