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Cyclopentane is dichlorinated and I have to write down the structures of all the dichlorinated cyclopentanes formed. I took monochlorocyclopentane and monochlorinated it. The point is that I get confused with the stereochemistry here since the answer is different from the one I have computed. Supposing I take monochlorocyclopentane, I can get the (1,1), (1,2) and (1,3) dichloro derivatives. The (1,1) is achiralic so it poses no problem. That means I get the following products:

1. 1,1-dichloro cyclopentane. I know that when the second chlorine is cis to the first one, we have a meso product. But when it is trans, are there two possible products (enantiomeric)? If yes, then a racemic mixture should be formed right?

2. 1,3-dichloro product (same problem as part (1)).

The correct answer is 5 products of which 2 are optically active. I would be very grateful if someone could give me a detailed description of this (diagrams would be appreciated but a description will do for I can figure out myself).

Thanks

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# Elementary dichlorination rxn

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