Question

Why doesn't 5-Chlorobicyclo[2.1.1]hexane have a chiral center?

Answer 1

http://answers.yahoo.com/question/index?qid=20080318141206AAMWkfj

Answer 2

Yeahhh that didn't really help

Answer 3

actually that wasn't it let me look again. the cl is in the wrong spot on that one

Answer 4

So looking at the picture here: http://www.chemspider.com/Chemical-Structure.4482248.html

Most of the carbon atoms have at least two hydrogen atoms attached, so none of them are chiral. The only ones that have one hydrogen attached are the one bonded to chlorine and the one directly across from it bonded to three other carbon atoms. Nether of these is considered chiral because if you follow the ring around either side, you encounter the same pattern of atoms. Therefore, the side chains are not considered different.

Answer 5

okay. that's what I thought but then 2-fluorobicyclo[2.2.2]octane is chiral. So I got confused

Answer 6

How is that chiral

Answer 7

That molecule is achiral as well...for the carbon attached to the fluorine atom and the one directly across attached to the three other carbon atoms, you get the same pattern on all three sides when you follow them around the ring.

Answer 8

My book and review packet fro my professor says otherwise... That's why I'm confused

Answer 9

Hmm well I'd like to know why it's chiral then too haha