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Topic: Aspirin + HCl + CH3OH mechanism?  (Read 8339 times)

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Offline JrChic

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Aspirin + HCl + CH3OH mechanism?
« on: December 01, 2008, 11:15:06 AM »
I can't figure out the mechanism for combining aspirin with HCl and CH3OH (methanol).

The study guide I'm using shows the final product as a benzoic ring attached to another ring. The second ring is 5 atoms, with one of them being an oxygen, it also has a double bond to an oxygen on one carbon, and the other carbon has OCH3 and CH3 attached.

The product would be C10H10O3.

any suggestions? thx a ton!
class of 2010

Offline azmanam

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Re: Aspirin + HCl + CH3OH mechanism?
« Reply #1 on: December 01, 2008, 02:30:17 PM »
First - which product are you describing.  See attached.

Second - am I reading your question correctly?  Does my scheme accurately depict what you are describing?

Third - I can't get to either product in one step using those reagents.  If I'm not drawing it correctly, can you try drawing it in Paint or some such program and posting it so we can get a better idea of what the question is asking.
Knowing why you got a question wrong is better than knowing that you got a question right.

Offline macman104

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Re: Aspirin + HCl + CH3OH mechanism?
« Reply #2 on: December 01, 2008, 03:32:30 PM »
Agreed Azmanam, I tried drawing it out, but could not get to any product that was described.

Offline JrChic

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oops, nevermind
« Reply #3 on: December 02, 2008, 12:03:07 PM »
i had the wrong starting material - it wasn't aspirin. we had just done an aspirin lab, so i decided that i was looking at aspirin i was starting with. sorry for the mistake and thanks for the *delete me* i also forgot to mention that you need to add head - missed the fine print!

JrChic

Offline azmanam

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Re: Aspirin + HCl + CH3OH mechanism?
« Reply #4 on: December 02, 2008, 12:15:13 PM »
so what is the right sm?
Knowing why you got a question wrong is better than knowing that you got a question right.

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