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Topic: Which is the most acidic hydrogen??  (Read 7152 times)

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Offline Cacoethes

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Which is the most acidic hydrogen??
« on: January 24, 2009, 04:33:05 PM »
Look up tetracycline in google images.

What's the most acidic alcoholic hydrogen on tetracycline and explain why.  Yeah I know the weaker the base the stronger its conj. acid, but it is confusing.

Thanks.
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Offline vhpk

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Re: Which is the most acidic hydrogen??
« Reply #1 on: January 24, 2009, 10:38:09 PM »
Quote from: Cacoethes on January 24, 2009, 04:33:05 PM
Look up tetracycline in google images.

What's the most acidic alcoholic hydrogen on tetracycline and explain why.  Yeah I know the weaker the base the stronger its conj. acid, but it is confusing.

Thanks.
Maybe the H of the phenol group, since the lone pair of electron on oxygen is delocalized on the benzene ring, the anion formed would be stable and hence, the H is the most acidic
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Offline Gregorian

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Re: Which is the most acidic hydrogen??
« Reply #2 on: January 25, 2009, 12:13:30 AM »
I agree with you vhpk
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Offline Cacoethes

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Re: Which is the most acidic hydrogen??
« Reply #3 on: January 25, 2009, 09:26:28 AM »
that makes a lot of sense, thank you very much!
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