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April 11th, 2018, 03:19 AM   #1
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Solubility question

The dropbox link to the question is: https://www.dropbox.com/s/ldyr3u1d5f...lease.PNG?dl=0

And i have also attached the question, but it isnt clear.

The question is regarding the Doxorubicin molecule:
a) would you predict the compound to be water soluble in the form presented?
b) would the solubility be pH dependent?

the answer given to both questions is yes, but it doesnt provide a reason.

I was thinking that for part a, the explanation is that the OH and NH2 can form H bonds with water

and for part b, i'm not too sure. because, if the molecule was ionised, then it would still be water soluble.

Any input would be appreciated! (my test is tomorrow)...
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April 11th, 2018, 05:01 AM   #2
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I would offer the ketone/aldehyde functional groups as the reason for solubility and the hydroxyl groups as the reason for pH dependence.
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April 11th, 2018, 05:04 AM   #3
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could you expand on your reasoning? for the hydroxyl groups, wouldnt they be soluble as both OH and O- ?
if they are ionised or unionised, then theyd still be soluble. im not sure why they would be pH dependent.
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April 11th, 2018, 08:45 AM   #4
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Inorganic mantra

Acid plus base makes salt plus water

Organic mantra

Acid plus alcohol (the C-OH) makes ester plus water.

So the esterification will be pH dependent.

However
Acid plus ketone is not normally so fruitful eg Adol condensation.
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