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I'm on the email list of an Organic Chemistry help website, and they sent out this problem:

http://orgomadesimple.com/june-9-email-practice-problem/

This got me thinking:

  • What if the nitrogen here was replaced with another oxygen atom?
  • Would it still be $sp^2$ hybridized?
  • Can oxygen molecules hybridize?

Thanks in advance for your help!

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    $\begingroup$ Changing that nitrogen to an oxygen would make an ester, right? $\endgroup$ – gilleain Jun 12 '15 at 13:08
  • $\begingroup$ It's similar, but not quite the same. I'd call it borderline. $\endgroup$ – Breaking Bioinformatics Jun 12 '15 at 13:59