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Topic: Naming of an organic compound  (Read 4204 times)

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Offline deutdeut

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Naming of an organic compound
« on: December 07, 2006, 09:30:06 PM »
My book has a problem like this:

Name the compound CH3C(OH)=C(OH)CH3

the answer is trans-2,3-dihydroxybut-2-ene

But isn't the functional group -OH is the principal functional group prior to C=C group and it should be designated as the ending?

Hence can the name be trans-but-2-ene-2,3diol?

Offline Custos

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Re: Naming of an organic compound
« Reply #1 on: December 08, 2006, 12:10:10 AM »
What is more annoying is that the structure doesn't make sense from a chemistry perspective. For one thing the name is the enol form (left structure) of the keto alcohol - more likely to be the predominant structure - and the trans/cis isomers will be easily inter-convertible. I understand that this is a "nomenclature problem" but you would at least think a text book would stick with realistic structures.  >:(

Offline deutdeut

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Re: Naming of an organic compound
« Reply #2 on: December 08, 2006, 12:35:24 AM »
So is the name correct or not?

Offline Albert

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Re: Naming of an organic compound
« Reply #3 on: December 08, 2006, 07:47:14 AM »
trans-but-2-ene-2,3diol?

I believe this to be the best answer (your book's, though, is not totally incorrect).

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