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Organic Question

Discussion in 'Pre-Medical - MD' started by TheGuy2000, Apr 25, 2004.

  1. TheGuy2000

    TheGuy2000 Member
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    Howdy folks,
    Hate to bring back some bad memories, but I'm struggling to find the mechanism which would get me from
    N-benzylphthalimide + hydrazine ----ethanol--> to benzylamine and phthallhydrazide.
    Thanks for any help. Does the hydrazine just attack the carbonyl here?
    I'm pretty sure it's a Gabriel Synthesis.

    Pax.
     
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  3. TheGuy2000

    TheGuy2000 Member
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    bumpy, plz help me :confused: organic is making lose my mind...
     
  4. Benjo

    Benjo Senior Member
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    what the hell are those compounds? Maybe give us an idea of what that nomenclature actually translates to in structure/functionality and we can help.
     
  5. liverotcod

    liverotcod Lieutenant Crunch
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    My organic instructor waved the magic mechanism wand on Gabriel synthesis and said, "Don't worry about this one. Just know Fisher esterification." Here's a web page on Gabriel synthesis. It certainly looks like the hydrazine could do nucleophilic acyl substitution on the each of the carbonyls, releasing R-NH2 from first one side of the ring, then the other.
     

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