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Topic: Identifying compounds  (Read 2786 times)

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Offline Pranav

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Identifying compounds
« on: May 06, 2013, 09:05:05 AM »
Clearly, x is A. Adding hydroxylamine and HCl gives B(y). Reaction of an oxime with H2SO4 converts it to ketone which does not match any of the given options. Therefore the answers should be A and B but the key states that it is A,B and C. ???


Offline sjb

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Re: Identifying compounds
« Reply #1 on: May 06, 2013, 09:20:08 AM »
Clearly, x is A. Adding hydroxylamine and HCl gives B(y). Reaction of an oxime with H2SO4 converts it to ketone which does not match any of the given options. Therefore the answers should be A and B but the key states that it is A,B and C. ???

Can you find a reference that says oxime + sulfuric acid  :rarrow: ketone?

Offline Pranav

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Re: Identifying compounds
« Reply #2 on: May 06, 2013, 09:29:21 AM »
Clearly, x is A. Adding hydroxylamine and HCl gives B(y). Reaction of an oxime with H2SO4 converts it to ketone which does not match any of the given options. Therefore the answers should be A and B but the key states that it is A,B and C. ???

Can you find a reference that says oxime + sulfuric acid  :rarrow: ketone?

Just found that this reaction is Beckmann rearrangement. But won't that change the configuration of the chiral carbon?

Offline Dan

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Re: Identifying compounds
« Reply #3 on: May 06, 2013, 10:05:45 AM »
Just found that this reaction is Beckmann rearrangement. But won't that change the configuration of the chiral carbon?

No, the configuration of a stereogenic migrating group is retained din this reaction. What gave you the impression that it would invert?
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Offline Pranav

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Re: Identifying compounds
« Reply #4 on: May 06, 2013, 10:08:04 AM »
Just found that this reaction is Beckmann rearrangement. But won't that change the configuration of the chiral carbon?

No, the configuration of a stereogenic migrating group is retained din this reaction. What gave you the impression that it would invert?

Woops, sorry for the foolish question. I messed up.

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