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Topic: reaction using a-pinene oxide  (Read 9891 times)

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Offline please5

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reaction using a-pinene oxide
« on: March 27, 2011, 05:03:59 AM »
a-pinene oxide is reacted with sulfric acid to create a molecule with m/z of 170. The reaction is occurs by adding hexane and then later washing the solid with water but i think that the hexane is simply used as a solvent and that the solid is simply washed with water. can someone help me figure out the product? i know that because of ring strain a carbocation shift occurs or a structure similar to limonene is created but i cannot figure out how a molecule with a mass of 170 is created since a-pinene oxide has a mass of 152 and this reaction is all about carbocation shifts.
« Last Edit: March 27, 2011, 05:15:21 AM by please5 »

Offline Honclbrif

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Re: reaction using a-pinene oxide
« Reply #1 on: March 27, 2011, 08:13:17 AM »
You're on the right track, but since there was a mass shift, you need to determine what caused it.

Think about the reactivity of carbocations: they can rearrange, but they can react in other ways as well.

What's the difference between 170 and 152? What ubiquitous molecule has the same mass?
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Offline please5

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Re: reaction using a-pinene oxide
« Reply #2 on: March 27, 2011, 12:59:58 PM »
damm... i cant figure out where the extra mass of 18 is coming from. i find it improbable that 18 more hydrogens are attached or that hexane (which i assume is simply the solvent) is somehow involved since its mass is 72. And since only one product is created (i think), i dont think that a-pinene oxide reacts with itself.

Offline Honclbrif

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Re: reaction using a-pinene oxide
« Reply #3 on: March 27, 2011, 01:46:14 PM »
Even concentrated sulfuric acid isn't pure H2SO4. There's at least one other molecule in there. What's its mass? Is it capable of adding to a carbocation?
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Offline nox

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Re: reaction using a-pinene oxide
« Reply #4 on: March 27, 2011, 04:00:41 PM »
^Arguably it's the most abundant molecule on Earth.

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