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Topic: Methyl Benzene  (Read 8558 times)

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Offline novice

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Methyl Benzene
« on: June 14, 2008, 04:16:54 AM »
This is a really simple question, but is methyl benzene planar and thus aromatic?

From the point of view of the methyl group, their is a tetrahedral configuration, but when we consider aromaticity, we only look at atoms attached immediately to the ring right?

Offline prophecy

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Re: Methyl Benzene
« Reply #1 on: June 14, 2008, 11:50:15 AM »
The way I see it, is that methyl benzene is not planar, it's tetrahedral. (Prototype Geometry). The phenyl substituent is just replace by a proton (H), so therefore it's tetrahedral. Toluene (a.k.a methylbenzene) is aromatic because of the phenyl substiuent or benzene ring. We look for the ring, that's it; very simple, we just look at for that benzene ring, and that gives the compound or whatever it is "aromatic" properties. For example, female hormones like estrogen is aromatic, and male hormones like testosterone isn't because the molecule does not contain that aromatic ring. The class of compounds are called Arenes.

Offline prophecy

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Re: Methyl Benzene
« Reply #2 on: June 14, 2008, 11:53:43 AM »
Sorry, benzene is planar because of the hexagonal arrangement, but if you need more information there's a good website here: http://www.cem.msu.edu/~reusch/VirtualText/react3.htm

Offline Yggdrasil

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Re: Methyl Benzene
« Reply #3 on: June 14, 2008, 12:05:46 PM »
This is a really simple question, but is methyl benzene planar and thus aromatic?

From the point of view of the methyl group, their is a tetrahedral configuration, but when we consider aromaticity, we only look at atoms attached immediately to the ring right?

This is correct.  When talking about aromatic rings, we say a molecule is planar if all of the sp2 carbons in the ring lie in the same plane.  You are absolutely correct that the hydrogens on the methyl group will lie outside of this plane.

Offline novice

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Re: Methyl Benzene
« Reply #4 on: June 14, 2008, 01:07:32 PM »
thanks!

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