Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: CaptainAwesome on September 22, 2011, 09:56:56 PM

Title: Having Trouble Seeing Molecular Orbitals For Stereoelectronic Effects
Post by: CaptainAwesome on September 22, 2011, 09:56:56 PM

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 (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!

Title: Re: Having Trouble Seeing Molecular Orbitals For Stereoelectronic Effects
Post by: james_a 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". :-)