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Does 1,4-dimethylcyclohexane have a chiral center?
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+ Chirality
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Does 1,4-dimethylcyclohexane have a chiral center?
As it is said in the definition of IUPAC, for a carbon atom to be chiral it should be attached to 4 different groups:
In case of 1,4-dimethylcyclohexane, you will see that the two groups on the right and on the left are identical. So in this case it's not Cabcd, it's Cabbc. If you alter one group (let's say the one on the right), these groups will no longer be identical, so you will have 4 non-identical groups attached to a carbon atom, and this atom will become a chiral centre.
Meso-compounds are compounds that have chiral centre but they also have a plane of symmetry so that they are still superimposable with their mirror image. Following is the example of a meso-compound from McMurry's book (Ref.1):
So a meso-compound must have a chiral centre by definition, but if a compound has a chiral centre, that doesn't necessarily mean that it's a meso-compound. And the answer to your question is no, 1,4-dimethylcyclohexane doesn't have any chiral centre.
References:
John E. McMurray, In Organic Chemistry, Ninth Edition; Cengage Learning: Boston, MA, 2016, pp. 133 (ISBN-13: 978-1-305-08048-5).
As it is said in the definition of IUPAC, for a carbon atom to be chiral it should be attached to 4 different groups:
In case of 1,4-dimethylcyclohexane, you will see that the two groups on the right and on the left are identical. So in this case it's not Cabcd, it's Cabbc. If you alter one group (let's say the one on the right), these groups will no longer be identical, so you will have 4 non-identical groups attached to a carbon atom, and this atom will become a chiral centre.
Meso-compounds are compounds that have chiral centre but they also have a plane of symmetry so that they are still superimposable with their mirror image. Following is the example of a meso-compound from McMurry's book (Ref.1):
So a meso-compound must have a chiral centre by definition, but if a compound has a chiral centre, that doesn't necessarily mean that it's a meso-compound. And the answer to your question is no, 1,4-dimethylcyclohexane doesn't have any chiral centre.
References:
John E. McMurray, In Organic Chemistry, Ninth Edition; Cengage Learning: Boston, MA, 2016, pp. 133 (ISBN-13: 978-1-305-08048-5).
As it is said in the definition of IUPAC, for a carbon atom to be chiral it should be attached to 4 different groups:
In case of 1,4-dimethylcyclohexane, you will see that the two groups on the right and on the left are identical. So in this case it's not Cabcd, it's Cabbc. If you alter one group (let's say the one on the right), these groups will no longer be identical, so you will have 4 non-identical groups attached to a carbon atom, and this atom will become a chiral centre.
Meso-compounds are compounds that have chiral centre but they also have a plane of symmetry so that they are still superimposable with their mirror image. Following is the example of a meso-compound from McMurry's book (Ref.1):
So a meso-compound must have a chiral centre by definition, but if a compound has a chiral centre, that doesn't necessarily mean that it's a meso-compound. And the answer to your question is no, 1,4-dimethylcyclohexane doesn't have any chiral centre.
References:
As it is said in the definition of IUPAC, for a carbon atom to be chiral it should be attached to 4 different groups:
In case of 1,4-dimethylcyclohexane, you will see that the two groups on the right and on the left are identical. So in this case it's not Cabcd, it's Cabbc. If you alter one group (let's say the one on the right), these groups will no longer be identical, so you will have 4 non-identical groups attached to a carbon atom, and this atom will become a chiral centre.
Meso-compounds are compounds that have chiral centre but they also have a plane of symmetry so that they are still superimposable with their mirror image. Following is the example of a meso-compound from McMurry's book (Ref.1):
So a meso-compound must have a chiral centre by definition, but if a compound has a chiral centre, that doesn't necessarily mean that it's a meso-compound. And the answer to your question is no, 1,4-dimethylcyclohexane doesn't have any chiral centre.
References:
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