Thursday, November 21, 2019

stereochemistry - Total number of stereoisomers of 2,3,5,6-tetrachlorooctane



Total number of stereoisomers for:


2,3,5,6-tetrachlorooctane



I tried the following combinations:
RRRR, SSSS, RRRS, SSSR, RRSS, RSRS, SRRS, RSSR, RSRR, SRSS, RRSR, SSRS, SSRR, SRSR.



So, total number of stereoisomers I got is 12, but my teacher says it's 16. I don't know how to figure out what other four isomers are.



Answer



If you have studied combinatorics, and if you know the fundamental principal of counting, then this is basically making a four letter word with two letters- R and S. Each place has two choices, and you have four spaces to fill, so you get 2×2×2×2= 16 optical isomers for this molecule. Since the terminal alkyl groups are different, so there is no chance of a meso-compound. And as Ivan rightly stated in the comment, to list the isomers, make all possible combinations of R and S(you have missed a few as pointed out by porphyrin in the comments)


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