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Topic: Help on finding chiral centers - and Calculating pKa  (Read 4292 times)

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Offline strinco

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Help on finding chiral centers - and Calculating pKa
« on: May 20, 2010, 01:31:57 AM »
Ok, im making an essay of an organic compound and i dont know why i chosen this one.
Here it is, its dexamethasone, i have to draw stereoisomers so i need to find out how many chiral centers does it have (ill draw just a pair cuz it might be madness to think i can draw them all)

I've marked quiral centers as red, i dont know if im wrong, or if im missing another one; thanks a lot



The other one is, is it possible to calculate the pKa for this compound? , i mean, some books gives you the pKa of certain acids and functional groups, but im wondering how is it possible to do it on this one.

By the way, im using BKChem to draw the structures

Offline strinco

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Re: Help on finding chiral centers - and Calculating pKa
« Reply #1 on: May 20, 2010, 02:42:27 AM »
okay haha, ive just realized that the first flagged carbon as quiral (the next one to de C-F) is non quiral.

Offline sjb

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Re: Help on finding chiral centers - and Calculating pKa
« Reply #2 on: May 20, 2010, 07:05:56 AM »
okay haha, ive just realized that the first flagged carbon as quiral (the next one to de C-F) is non quiral.

Are you sure? All the carbons attached to the tertiary halide look chiral to me. What is the definition of a chiral centre?

Offline strinco

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Re: Help on finding chiral centers - and Calculating pKa
« Reply #3 on: May 20, 2010, 09:49:07 AM »
oh my... you are right, ive made a big mistake and its almost class time  :( , i dont know why ive changed my mind and decided to "disappear" that chiral centre, i tought for a moment that it was attached to two sets of HC.

At least im not having problems with SN reactions.... this was suposed to be my final essay, hopefully the teacher will have mercy on me ;S .

Thanks a lot sjb

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