Which direction do the equatorial positions point?

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Which direction do the equatorial positions point?

Postby Chem_Mod » Fri Apr 19, 2013 10:47 pm

Question: Hi, Professor Lavelle. When drawing the most stable chair conformations, if we start numbering our carbon atoms clockwise with the upper-right C atom being carbon #1, in which direction would the 3rd carbon's equatorial position point (to the left or right)? Similarly, in which direction would the 6th carbon's equatorial position point (to the the left or right)? Does it matter in which direction they point? If so, what positions would the same equatorial positions on the 3rd and 6th carbons of the ring-flipped-chair conformation be pointing? Thank you.
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Re: Which direction do the equatorial positions point?

Postby Chem_Mod » Fri Apr 19, 2013 10:48 pm

Answer: C#3 (the way you have numbered it) would have the equatorial pointing to the left. C#6 would be pointing to the right. They cannot really point the other way as that would be sticking into the ring. After a ring flip, the original equatorial bonds on C#3 and C#6 will become axial. The new equatorial bonds will still be pointing to the left (for C#3) and right (for C#6). There are plenty of examples of chair conformation drawn throughout the course reader, take a look at them more.


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