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Topic: Which one (hydrocodone/heroin/oxycodone) is made via nucleohphilic acyl substitu  (Read 8666 times)

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Offline theanonymous

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Which one (Hydrocodone, Heroin, or Oxycodone) is made via nucleohphilic acyl substitution using one of the natural alkaloids as the nucleophile?
« Last Edit: April 13, 2013, 11:53:41 AM by Arkcon »

Offline theanonymous

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:(
I don't know the answers to any of these...

Offline Arkcon

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Try looking up some of the compounds mentioned in part A.  You'll learn something about the nature of those drugs, you'll be able to answer the first part, and you'll also be on your way to understanding some of the rest.
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline theanonymous

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Try looking up some of the compounds mentioned in part A.  You'll learn something about the nature of those drugs, you'll be able to answer the first part, and you'll also be on your way to understanding some of the rest.

I did try but there was a lot of information regarding them!
I have no idea why my teacher put this on our Webassign HW assignment because I dont see how it relates to what we're learning :(

Offline Arkcon

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I ssume from the title that some of this drugs are a natural product that is altered "via nucleohphilic acyl substitu ..."tion. :)  So why not try to see which are naturally occurring, and which are modified.  That should be the first sentence on Wikipedia.
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline theanonymous

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I ssume from the title that some of this drugs are a natural product that is altered "via nucleohphilic acyl substitu ..."tion. :)  So why not try to see which are naturally occurring, and which are modified.  That should be the first sentence on Wikipedia.

What wikipedia page?

Offline discodermolide

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@theanonymous, you know better than to cry, sit down and look at the structures and the answers will be obvious. I assume you can also use search engines to find things such as Google.

What sort of compounds with what sort of functional groups form hydrochloride salts?
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Offline theanonymous

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@theanonymous, you know better than to cry, sit down and look at the structures and the answers will be obvious. I assume you can also use search engines to find things such as Google.

What sort of compounds with what sort of functional groups form hydrochloride salts?

Is the answer to B heroin? since you can get an acyl group from that?

Offline discodermolide

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If you acylate morphine you get heroin.
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Offline theanonymous

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If you acylate morphine you get heroin.

So the answer to B is heroin?

Offline discodermolide

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Offline theanonymous

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Offline theanonymous

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So for the structure...would it be...

CC(=O)OC(C)=O

Offline discodermolide

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Yes you can use acetic anhydride or the acetyl chloride, either will work.
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Offline theanonymous

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Yes you can use acetic anhydride or the acetyl chloride, either will work.

For C, would the answer be Carbon (C)? as in H is really bonded to carbon

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