HOW is ochem destroyer #127 [8]???

[Kneecoal]

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i don't know what i'm missing, but it's driving me crazy. how are there 8 chiral carbons on this thing?? i feel like a lot of them that they starred have 2 of the same kinds of groups, and so it shouldn't be chiral. can someone please explain this to me?

 

[loveoforganic]

can you post the molecule

 

[Kneecoal]

hah ok so i tried drawing it out on word/paint... i know it's pretty bad, but it serves its purpose

thanks in advance!

 

[loveoforganic]

Ok I counted 8, so the book's right. When you look for chirality, you have to consider the entirety of the substituent, not just the connection atom. e.g. you can have 4 bonds to carbon, but one carbon might connect to iodine, one to bromine, one to chlorine, and one to fluorine, so the center carbon would be chiral.

 

[Kneecoal]

Ok I counted 8, so the book's right. When you look for chirality, you have to consider the entirety of the substituent, not just the connection atom. e.g. you can have 4 bonds to carbon, but one carbon might connect to iodine, one to bromine, one to chlorine, and one to fluorine, so the center carbon would be chiral.

hmm, all right. i tried it that way and i can see why it's 8. thanks!