Methods for Chem Final

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DesLee26
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251352
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Methods for Chem Final
Updated:
2013-12-06 22:30:34
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CHM 201
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  1. Methods for Preparing Alkyl Halides: 

    1) From alkanes
    free rad halogenation

    R-H + X2--> R-X + H-X
  2. Methods for Preparing Alkyl Halides: 


    From other halides
    R-X + I- --> (in acetone) --> R-I + X-
  3. Sn2 reactions
    - orger of reactivity
    - stereochemistry

    • Order of reactivity: 
    • - CH3X > primary > secondary (doesn't occur on tertiary)
    • - stereospecific: causes inversion
  4. Sn1
    - nucleoophile?
    - steps?
    - reactivity?
    - stereochemistry?
    - very weak solvent

    • Steps:
    • 1) formation of carbocation (rate limiting)
    • 2) nucleophilic attack on the carbocation
    • 3) loss of proton to solvent ( if the nucleophile is water or an alcohol

    • - 3> 2> 1> Ch3X
    • - because its carbocation is planar, it can approach from both faces, causing a racemic solution (front side: retention of config/ back side: inversion)
  5. E1 reaction
    - reactivity
    - steps
    - 3> 2>>1

    • Steps:
    • 1) unimolecular ionization to give a carbocation (rate-limiting)
    • 2) Deprotonation by a weak base gives the alkene
  6. E2
    - base
    - reactivity
    - Steps
    - products
    - Stereochemistry
    • - can be bulky
    • - 3>2>1
    • - Steps:-- single step; base abstracts proton on carbon next to leaving group and the leaving group leaves, forming an alkene
    • - can form multiple products based on substituted
    • - Stereospecific: they must be anti to each other

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