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I came across this compound in the Black Book of Organic Chemistry by Ashish Mishra. The question asked whether this compound could show geometrical isomers.

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Now, I know the compound has the following two stereoisomers:
enter image description here

However, these are optical isomers, they look like cis/trans compounds, but the distances between any two atoms are identical for both structures, unlike in normal cis/trans isomers. So, according to me the answer should be no, this compound cannot show geometrical isomerism, but according to the answer key, it can show geometrical isomerism.
So, can someone tell me why I am wrong, or is it the book that's wrong?

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  • $\begingroup$ They are stereoisomers that are enantiomers. Each one is optically active. The geometrical E-double bond doesn't exist. See this. $\endgroup$
    – user55119
    Mar 8 at 15:54

1 Answer 1

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First of all you cant say wether cyclohexane derivatives has geometrical isomers or not just by drawing the structure given in question. That structure is wrong it exists in chair form its most stable form. As there is no pure enantiomer given in question the upper methyl can be at axial or equatorial position. Hence in these cases the distance will be different. Try drawing its conformer

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  • $\begingroup$ The question is about a cyclohexene derivative $\endgroup$
    – Ian Bush
    Mar 12 at 7:42

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