[zhouduck]

Is 2-bromobicyclo[2.1.1]hexane chiral? I think is achiral; however my solution says it's chiral....

[Jorriss]

I'm not sure what direction you name these from, is the bromine on the 1 or 2 carbon side?

[zhouduck]

You're right. I should name the cycloalkane from the longest circle according to the IUPAC rules. As a result, it should be chiral. Thank you!

[Dan]

It is chiral. Here are a few ways of looking at it:

The carbon bearing the bromine has 4 different substituents, it is an asymmetric centre. It is also the only asymmetric centre, therefore the compound could not be meso and it must be chiral.

The molecule has no plane or centre of symmetry, so it must be chiral.

The mirror images are non-superimposable (make models if necessary), it is chiral

[zhouduck]

Thank you, Dan! :]

[mcdonabe]

Easy rule of thumb, if you see a carbon that has four unique substituents (and there are no planes of symmetry) there is chirality