Organic Chemistry question

[NatashaColorado]

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Does anyone know if 1-methylcyclohexane considered a meso compound? What about 1-chloro-1-methylcyclohexane (with chloride and methyl group on the same carbon)? I remember that we were "cutting" through substituents on the same carbon in O Chem class and considered them meso, but the answer for 1-chloro-1-methylcyclohexane is " achiral but not meso". Why is it not meso?

 

[hurricaneuro]

1-chloro-1-methyl cyclohexane is achiral because all of it's carbons have atleast two of the same substituents on it. Five of the carbons have two Hydrogens attached so right away they are achiral, and the Carbon-1, although it has a methyl and chloro, has identical sides due to the ring. Therefore it is achiral (does not have four different substituents), but if you split it in half it would not look the same (so not meso either).Make sense?

 

[SonofanOpt]

1-chloro-1-methyl cyclohexane is achiral because all of it's carbons have atleast two of the same substituents on it. Five of the carbons have two Hydrogens attached so right away they are achiral, and the Carbon-1, although it has a methyl and chloro, has identical sides due to the ring. Therefore it is achiral (does not have four different substituents), but if you split it in half it would not look the same (so not meso either).Make sense?

Now if it was dichloro cyclohexane and both Choros on the 1 carbon were cis (both dashes or bold bolded), then it would be a meso compound... just to add to what he said.

 

[NatashaColorado]

So, 1-methylcyclohexane is meso, right? We can cut through one substituent?

 

[TedyBearSuicide]

So, 1-methylcyclohexane is meso, right? We can cut through one substituent?

1-methylcyclohexane:

This is NOT meso.