[smghz]

This problem is mind boggling. How could the stereocenter with the hydroxyl be classified as S? I mean, after rotating the molecule to make H dashed, we still have the order from OH to the cyclohexane with the Cl to the other part of the cyclohexane, which is clockwise. Can someone help me visualize this, please? thanks

[sjb]

What priorities have you assigned your groups? Are you happy the halide is also S?

[smghz]

OH = 1
Cyclohexane (w/ Cl) = 2
Cyclohexane (other part) = 3
H = 4

My issue isn't with prioritizing groups. It is in visualizing how I can rotate the structure so that I can make H dashed and have a counterclockwise arrangement, which entails Cl being on the left. How is that possible? I mean, the H has neither wedged nor dashed line, it's just on the plane of the page. So a rotation 90 degrees would have the Cl on the back, right?

[sjb]

Sorry, missed the priorities in your original post.

Perhaps a short-cut in this case but if you're happy the carbon bearing the chlorine is S my thoughts were that for the purposes of this,
* the chlorine is identical in priority to how the hydroxyl sits on the other chiral centre
* if the compound was meso it would be R,S
* so it's S,S

You could also look at it as the highest priority group is at the back, which reverses any assignment.

Or alternatively don't forget the hydrogen (on the carbinol) is coming out of the plane so just rotate the molecule around the C-C bond that contains the two chiral centres

[Babcock_Hall]

One can also make a model and physically rotate that.