# Systematic Approach to Finding Number of Isomers [duplicate]

I have this compound

I want to know how many isomers (including stereoisomers) may have this constitution. Is there a systematic approach towards solving such types of problems related to the total number of isomers?

Note: The above compound has 64 stereoisomers (from textbook).

• Yes there is a systematic approach: there are 6 things which may be one way or another, hence $2^6$ isomers. May 23, 2018 at 15:01
• @IvanNeretin Do you mean the chiral centers and the double bonds? May 23, 2018 at 15:17
• I mean the double bonds and the atoms in the ring with attached side chains (the latter are also chiral centers, but that's irrelevant). May 23, 2018 at 15:19
• @IvanNeretin Ok Thankyou. But what about total number of isomers including the structural isomers also? May 23, 2018 at 15:21
• That number is a great deal greater and can't be estimated easily. May 23, 2018 at 15:28

For instance, the given framework has 4 stereo centers, hence theoretically, you have $2^4 = 16$ stereoisomers for that compound alone. If your book says it has 64 stereoisomers, it probably has counted geometric isomers of conjugated double bonds (E/Z isomers) as well. All these 64 isomers are illustrated as compound 1 in the scheme below where each red asterisk represent a chiral center. Note that, since the ring has three different substitution groups, none would lead to symmetry in the molecule. Thus, all theoretical amount is equal to the actual number of isomers. Now, question is whether you need to count the stereoisomers for this framework only or not. If it is only for this framework, then the number is 64. But, if you want to change the framework by moving the substitution around, that would be a different story.
• If, for example, you want to move substituents around the ring then this is the same as the number of ways of choosing 5 objects out of 8 which is $8!/(5!3!) = 56$, then you have the stereo-centres to consider also, $2^4$ for each of these 56 and then multiply by the number of E,Z configurations. Quite a few thousand. May 24, 2018 at 7:36