Question

What are the stereoisomers of a cyclohexane with 5 -OH groups and one -CH3O group?

What are the stereoisomers of a cyclohexane with 5 -OH groups and one -CH3O group?

Homework Answers

Answer #1

First you need to determinate the number of chiral carbons. then you can say how much stereoisomers have the molecule.

In this case, the carbon 1 (OCH3) it's not chiral, because two of his bonds are the same. Same thing happen with Carbon 4 (the bottom with the OH). So the others carbons (2,3,5,6) are chiral. This means that you have 4 chiral centers, so the number of stereoisomers are:

2n = 24 = 16

You may have 16 different stereoisomers for this molecule. I'll draw four of them so you can get the idea of how to draw the rest of them. In the next picture you have 6 of them, all you have to do is keep alterning between the axial and ecuatiorial position:

If you need more explanation to get the rest of the stereoisomers, tell me in a comment and I'll gladly tell you how.

EDIT:

Like I said in the comments, this a derivate of a inositol. One of the groups is replaced with a CH3O- group. With this, you can actually draw 16 stereoisomers. The first 8 are in the picture below. For the next 8 you just have to change the orientation of the metoxi group on each stereoisomer:

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