Destroyer Ochem Question

[D.D.S.]

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Hi, Number 37 on destroyer Ochem about 1,3-dimethylcyclohexane asking about how many stereoisomers it has . since there are 2 chiral centers (2^n rule), i chose 4 stereoisomers, but the explanation says there are only 3because of the meso compound not counting? arent meso compounds stereoisomers anyway??

and if not, then of the remaining, which three are the stereoisomers.. i only see 2..... can you explain this question to me..

Thank you!

 

[quikag1]

In cyclic compounds, the cis compound will be the meso compound and the trans isomer will exist as enantiomers. So all together you get 1 for the cis and 2 for the trans which equals 3. Its basically just a textbook rule. anytime that you have 2 chiral carbons and a plane of symmetry you get a meso compund. I hope this helps its kinda hard to understand without showing you a picture.

 

[D.D.S.]

ohhhhhhhhh i get it.. there will be two cis, but they are the same so it counts as one....



thanks a lot!!