[Kobsessed]

Ok soI have this worksheet showing 4 isomers of menthole. 1) (-) menthol, 2) (+) menthol, 3) (+) isomenthol, and 4) (+)neo menthol.

I have to determine what each pair is. a) Identical b) Enantiomer c) Not related d) Diastereomer e) Constitutional isomer


1&2:

1&3:

1&4:

2&3:

2&4:

3&4:

I don't think any of these are constitutional isomers, they can't be identical because they have different configurations in space. I'm thinking all of them are Diastereomers since they are not mirror images but just have the atoms arranged in different space. But I'm pretty sure I'm wrong because surely I'm missing out on something here.

[sjb]

You might want to have a look through the definitions of the various types of isomerism, at e.g. http://en.wikipedia.org/w/index.php?title=Isomer&oldid=272418794 ?

[AWK]

Search wikipedia for menthol

[Kobsessed]

Ok so today we did a TLC test on (+) and (-) menthol and (+) neomenthol. The (-) and (+) menthol had the same Rf values while the other did not. These were all on the same plate. So according to my text this would be mean (-) menthol and (+) menthol are identical stereoisomers right?

One thing for sure though is that none of these are constitutional isomers and they are in fact "related" so the Not Related option won't be needed either right?

[AWK]

Though Rf values mean almost nothing (thousands of compounds can show the same Rf)it is a fact that both enantiomers (+ and  -menthols) should show the same Rf.