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Topic: Having Trouble Seeing Molecular Orbitals For Stereoelectronic Effects  (Read 2311 times)

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Offline CaptainAwesome

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Hi everyone,

I'm working on a problem set for my advanced organic class, and I'm stuck on this problem : http://imgur.com/EUCQs
"Give the products and the stereochemical outcomes for each of the following transformations. Justify your answer using clearly drawn figures. Label and identify any relevant stereochemical or conformational issues."

I know that it's an epoxidation reaction, but I'm having trouble figuring out how the position of the methyl group would affect the stereochemical outcome. The only thing I can think of is some sort of anomeric effect with the oxygen, but I can't visualize the orbitals involved.

Any help or guidance would be greatly appreciated!

Offline james_a

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Re: Having Trouble Seeing Molecular Orbitals For Stereoelectronic Effects
« Reply #1 on: September 27, 2011, 11:07:19 AM »
What's going to be the most stable conformation here? Once you figure out the most stable conformation, you should be able to figure out the preferred face for attack of the epoxidizing agent.

The phrase you want to look up is "allylic strain". :-)

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