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Topic: Organic Chemistry: Identity the Reagents!  (Read 4177 times)

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Offline Kayla

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Organic Chemistry: Identity the Reagents!
« on: December 13, 2009, 11:28:14 PM »
I need help on 15-20. I cant figure out what reagents to use. Please help thanks

Offline sjb

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Re: Organic Chemistry: Identity the Reagents!
« Reply #1 on: December 14, 2009, 02:18:14 AM »
Do you know how to get there if there was no labelling introduced in those reactions?

Offline Schrödinger

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Re: Organic Chemistry: Identity the Reagents!
« Reply #2 on: December 14, 2009, 03:54:05 AM »
Seeing that you've solved most of the other ones, this has got to help you :

15 and 16 : Anti-addition of OD instead of OH.

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Offline Zainb

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Re: Organic Chemistry: Identity the Reagents!
« Reply #3 on: December 14, 2009, 05:02:40 AM »
10 the ozonolysis of olefins to ozonides and the subsequent conversion to aldehydes  in reductive workup conditions
11 and 14 is oxidation of hydroxy group with Dess-Martin periodinane.

Offline Borek

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Re: Organic Chemistry: Identity the Reagents!
« Reply #4 on: December 14, 2009, 05:19:20 AM »
Really no need to cry in blue.
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Offline bromidewind

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Re: Organic Chemistry: Identity the Reagents!
« Reply #5 on: December 16, 2009, 09:04:01 PM »
17. Use OsO4 and D2O2 -> Syn addition of OD
      Or you can use cold, dilute KMnO4, followed with -OD, D2O.
15, 16. Use a peroxyacid (peroxyacetic acid, MCBPA) to form an epoxide ring, then use D3O to open the ring and get anti-addition of OD
18. Pd/BaSO4, quinoline
Not sure about 19
20. 2 D2 and a metal catalyst like Pt, Pd, or Raney nickel

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