Stereogenic centre of 3-methylcyclohexanone

  • Thread starter shaurya
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In summary, the question asks about locating the stereogenic centre in 3-methylcyclohexanone. The conversation discusses the possibility of the carbon attached to the methyl group being the stereogenic centre, despite its attachment to multiple groups. The responder clarifies that the entire attached structure must be considered, not just the first attached atom. It is also mentioned that there may be additional stereogenic centres at the ortho and para positions.
  • #1
shaurya
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Homework Statement


Locate the stereogenic centre(chiral centre) in 3-methylcyclohexanone.


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The Attempt at a Solution


According to my reasoning there should be no stereogenic centre at any carbon of the ring,but the textbook says that the carbon attached to the methyl group is a stereogenic centre. Since the carbon is attached to H,CH2,CH3,CH2 it cannot be stereogenic(due to 2 methylene groups).
Is there any problem in my reasoning?
 

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  • #2
It is not only the first attached atom that counts, you need to take whole attached structure into account - that is, walk attached chain and compare - if it is identical to the end, it is identical, if there is a difference somewhere - it is different. Here first carbons AFTER CH2 are different.
 
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  • #3
Ok thanks Borek but I had one other question in mind ,so then would there be more than on e stereogenic centres on this compoung at ortho and para positions?
 

Related to Stereogenic centre of 3-methylcyclohexanone

What is a stereogenic centre?

A stereogenic centre, also known as a stereocentre, is a carbon atom in a molecule that is bonded to four different groups. This results in the carbon atom having non-superimposable mirror images, making it chiral.

How many stereogenic centres does 3-methylcyclohexanone have?

3-methylcyclohexanone has one stereogenic centre, which is the carbon atom bonded to the methyl group, the cyclohexane ring, and two other substituents.

What is the significance of the stereogenic centre in 3-methylcyclohexanone?

The stereogenic centre in 3-methylcyclohexanone is important because it gives the molecule chirality, meaning it has two non-superimposable mirror images. This can affect the molecule's physical and chemical properties, such as its ability to rotate plane-polarized light and its reactivity in reactions.

How is the configuration of the stereogenic centre determined?

The configuration of a stereogenic centre is determined by the priority of the four substituents bonded to the carbon atom. The Cahn-Ingold-Prelog rules are used to assign priorities based on the atomic number of the substituents. The lowest priority group is placed in the back, and the remaining groups are arranged in a clockwise or counterclockwise direction to determine the configuration.

Can the stereogenic centre in 3-methylcyclohexanone be converted to its enantiomer?

Yes, the stereogenic centre in 3-methylcyclohexanone can be converted to its enantiomer by breaking and reforming bonds to the carbon atom. This can be done through chemical reactions or physical processes such as heating or cooling. Enantiomers have identical physical and chemical properties, except for their interaction with chiral environments such as polarized light or chiral catalysts.

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