OCHEM meso

[OSUkid]

How in the world is cis-1,2-dimethylcyclopropane a meso compound. If you convert the wedges into dashes, vice versa it becomes an enatiomer and cannot be superimposed.
How??
Because I know cis-1-methylcyclohexane with an OH group on one of the carbons is an enatiomer. So how is this any different .

Please reply

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[GBP12]

How in the world is cis-1,2-dimethylcyclopropane a meso compound. If you convert the wedges into dashes, vice versa it becomes an enatiomer and cannot be superimposed.
How??
Because I know cis-1-methylcyclohexane with an OH group on one of the carbons is an enatiomer. So how is this any different .

Please reply

First of all, your naming in the second compound is off, if it has an OH it should be a cyclohexanol and if the methyl is adjacent to the OH it would be cis(or trans) 2-methylcyclohexanol.

The reason for cis 1,2-dimethylcyclopropane being a meso compound is the inner line of symmetry and if you were to draw the mirror image and flip it over, it would be identical to the original stereochemistry. Even if you were to put in dashes for wedges, you could then just flip the molecule over and rotate to give you the identical compound.

 

[OSUkid]

Bro I know if you flip it over its identical hence why I think its an enatiomer but it cannot be superimposed hence why i thinks its not meso
Ok so what about cis-1-methylcyclohexanol
It's cis and can be wedged or dashed and it an enatiomer, so whats the difference?
And how is cis-1,2-dimethycyclohexane a meso , but cis-1-methylcyclohexanol is an enantiomer. Also I am doing internal plane of symmetry, so the triangle cant have internal plane of symmetry if two substituents are next to each other as to why I think when mentioned before 1,2-dimethylcycloprone is not meso

 

[DAT Destroyer]

How in the world is cis-1,2-dimethylcyclopropane a meso compound. If you convert the wedges into dashes, vice versa it becomes an enatiomer and cannot be superimposed.
How??
Because I know cis-1-methylcyclohexane with an OH group on one of the carbons is an enatiomer. So how is this any different .

Please reply

Cis-1, 2-dimethylcyclopropane has chiral carbons.....AND a plane of symmetry. No symmetry is present in the 2-methylcyclopropanol.

Hope this helps.

Dr. Romano

 

[OSUkid]

How are these molecules achiral? You cant superimpose them unless you rotated it right,? I would think there just enatiomers.
I spent too many damn hours studying these stupid concepts its so annoying!
THATS AN ENATIOMER!!!!!!!
lol I am so heated

 

[DentalGirl5]

It's overall achiral because it's meso.

 

[DAT Destroyer]

View attachment 192861
How are these molecules achiral? You cant superimpose them unless you rotated it right,? I would think there just enatiomers.
I spent too many damn hours studying these stupid concepts its so annoying!
THATS AN ENATIOMER!!!!!!!
lol I am so heated

These are meso compounds and they represent the same molecule

 

[OSUkid]

These are meso compounds and the represent the molecule

So both of them are there own meso? Since you cant have two meso's only one.

 

[510586]

So both of them are there own meso? Since you cant have two meso's only one.

Yea meso is always to itself. Enantiomers and diastereomers are comparing 2 separate compounds. Somewhat correct me if I'm wrong but that's how we did it in class.

 

[cacajuate]

Remember you only need 3 weeks to study for DAT. I expect scores in that time frame.

 

[DAT Destroyer]

So both of them are there own meso? Since you cant have two meso's only one.

For this problem there is only a single meso compound. In advanced organic chemistry, it is possible for a molecule to have meso 1 and meso 2, but you will never encounter something like this for the DAT. For an exercise, prove this is a meso compound. Simply establish R/S configuration at these carbons. You will find half the molecule is an R and half is an S. Since the same groups are attached, you have a meso compound. Many organic text books will show examples of meso compounds.

Dr. Romano

 

[OSUkid]

Remember you only need 3 weeks to study for DAT. I expect scores in that time frame.

Dont worry Im taking Ochem right now Im gonna master it before the DAT next spring