I encountered this question in the Black Book of Organic Chemistry by Ashish Mishra while preparing for a college entrance exam.
According to the answer key the answer is 12. I have only managed to draw 11 possible structures.
If someone could help me find out the 12th structure it would be greatly appreciated.
In this the 1st, 2nd, 5th, and 6th structures are optically active, giving a total of $7+4 =11$ compounds.
PS: I used this to draw these structures. If there is more preferable way to upload structures let me know and I will update them.
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1 Answer
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The 7th structure is also optically active. (1S,2R)-1-(Chloromethyl)-2-methylcyclopentane is different from (1R,2S)-1-(chloromethyl)-2-methylcyclopentane.
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$\begingroup$ The molecule (1S,2R) exists here. But the molecule (1R,2S) is not produced here. $\endgroup$– MauriceCommented Feb 3 at 16:45
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$\begingroup$ @Maurice I believe both will form depending on which methyl group is chlorinated, is the answer not correct? $\endgroup$– GrimmCommented Feb 3 at 17:54
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$\begingroup$ Yes, Grimm. Sorry ! It is correct. I had not thought about this possibility. Thank you. $\endgroup$– MauriceCommented Feb 3 at 21:28