Extras for Exam I

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  1. Gilman Reagent 
    - take __ (works best with __)
    - treat with __
    - R can be __
    • alkyl halides
    • R-Br
    • lithium metal
    • alkyl, vinyl, aryl
  2. second alcohols turn into. Tertiary alcohols are __. You would have to do what?
    • ketones
    • inert to oxidation technically
    • you'd have to break the CC bond
  3. Ways to oxidize that we are using?
    NaCr2O7/H2SO4

    NaOCl
  4. Condensation reactions will form the __.

    if there are no H on the carbon, you won't __ it to a __.
    ester

    oxidize

    carbonyl
  5. The __ is very difficult to make. They are very easily __.
    • aldehyde
    • oxidized
  6. PCC Oxidizes primary acohols to __.

    Secondary alcohols to __
    aldehydes

    ketones
  7. pcc IS __
    • CrO3
    • pyridine
    • HCl
  8. What are some qualitative tests?
    chromium tests: primary and secondary go from orange to green, while tertiary don't react
  9. DMSO (__) 
    - Primary --> __ and Secondary --> __
    - same as __. 
    - higher yielding to __.
    - no __.
    • Swern oxidation
    • aldehydes
    • ketones
    • PCC
    • PCC
    • heavy metals
  10. __ shouldn't be used on primary because you get both __ and __.
    • bleach
    • aldehydes
    • acids
  11. Reduction: __
    • LiAlH4
    • NaBH4
    • H2 and Raney Nickel
  12. Conversion of Alcohol into a LG
    • 1) Tosylate (a leaving group if its CA is stable and strong
    • -- R-OTs= good LG
    • -- You can reduce an alcohol to an alkane with LiAlH4. H- will remove the OTs

    2) Alkyl Halides (HX)
  13. __ is a good solvent because it is basic. 

    Stereochemistry does what with Tosylates?
    pyridine

    remains because the reaction is between O and Cl, not O and C
  14. For reduction,
    __ is 98%. It either goes or it doesn't.
    catalytic hydrogenation
  15. Sn1 reactions
    - which does it?
    - which carbocations won't rearrange?
    - which will?
    - what happens with primary?
    • tertiary and secondary
    • tertiary
    • secondary
    • react slowly; not the way to go
  16. What does the Lucas Test distinguish between?
    • tertiary, secondary, primary
    • tertiary reacts in less than one minute
    • secondary reacts in one to five
    • primary reacts in several minutes to sevearl days
  17. alkene qualitatitve test
    reddish brown --(Br2)--> colorless
  18. To convert primary and secondary to alkyl halides, what do we use?

    - All are __
    • SOCl2
    • PBr3
    • P/I2

    SN2
  19. Which shift if faster?
    methyl
  20. Types of esters
    • Fischer
    • Tosylate
    • sulfate
    • nitrate
    • phosphate
  21. Sulfuric and phosphoric acids are __ in the reaction. The __ of the acid is removed. The __ of the ROH stays.
    • catalysts
    • OH group
    • H
  22. Protection of alcohols: use what?

    What kind of reaction?

    Run in presence of what?

    It then becomes what?
    chlorotrimethylsilane

    Sn2 (split out HCl)

    pyridine

    no longer an alcohol but a silyl ether
  23. What is the reverse reaction for protecting groups?
    dilute the acid; deprotonate

Card Set Information

Author:
 DesLee26
ID:
 258310
Filename:
 Extras for Exam I
Updated:
2014-02-05 01:25:10
Tags:
CHM 202
Folders:
Organic Chemistry
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