Is 1-ethyl-4-iodocyclohexane chiral?

Question

I can't tell if it has stereocenters. I'm confused because the iodo and the ethyl are on opposite sides, possibly creating a plane of symmetry. But doesn't the ethyl create an asymmetry because it can't just go straight out from the cyclohexane. It has to have a bend in it, which would create asymmetry. ...Help.

Answer 1

Not chiral, but you are correct in that there are stereocenters, the ethyl and iodo can be on the same face of the ring or on opposite sides of the ring. So you can have geometric isomers (similar to cis and trans double bonds). However because there is a plane of symmetry (draw a plane between the 1 and 4 positions of the ring), the molecule is not chiral. Simple rotations around bonds give different conformations and since the energy barrier to rotation is so low no asymmetry arises. In cases where there is very restricted rotation around a bond "atrope" isomers have been observed.

Answer 2

not chiral, it has a plane of symmetry through the 1,4 carbons of the hexane ring... both sides count the same way from both carbon 1 and carbon 4

Answer 3

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