Cis/trans disubstituted cyclohexanes help

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In summary, cis and trans disubstituted cyclohexanes refer to the spatial arrangement of substituents on a cyclohexane ring. Cis disubstituted cyclohexanes have the two substituents on the same side of the ring, while trans disubstituted cyclohexanes have them on opposite sides. This affects the stability of the molecule, with cis being less stable due to steric hindrance. Ring flipping is possible for these molecules, leading to a different spatial arrangement. The shape of cis/trans disubstituted cyclohexanes also impacts their physical properties, such as boiling point, melting point, and solubility. Some common examples of these molecules include cis-1,
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undertoes
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I understand that a cyclohexane is usually more stable when the substituted group, like methyl, is in the equatorial axis.

However, is it possble to determine the stability between, say, trans-1,2-dimethylcyclohexane and cis-1,3-dimethylcyclohexane. My guess is that the trans-1,2-dimethyl is least stable because the methyl groups are closer together?

how about trans-1,4-dimethylcyclohexane and cis-1,4-dimethylcyclohexane? they are both on opposite sides, so how can you tell?
 
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  • #2
You need to draw a Fisher projection
 
  • #3
Actually, it's a Newman projection.
 

Related to Cis/trans disubstituted cyclohexanes help

1. What is the difference between cis and trans disubstituted cyclohexanes?

Cis and trans refer to the spatial arrangement of substituents on a cyclohexane ring. In cis disubstituted cyclohexanes, the two substituents are on the same side of the ring, while in trans disubstituted cyclohexanes, they are on opposite sides of the ring.

2. How do cis/trans disubstituted cyclohexanes affect the molecule's stability?

The stability of a molecule is affected by the spatial arrangement of its substituents. Generally, cis disubstituted cyclohexanes are less stable than trans disubstituted cyclohexanes, as the bulky groups on the same side of the ring experience steric hindrance.

3. Can cis/trans disubstituted cyclohexanes undergo ring flipping?

Cis/trans disubstituted cyclohexanes can undergo ring flipping, which is the interconversion between the two chair conformations of the molecule. This can result in a different spatial arrangement of the substituents.

4. How does the shape of a cis/trans disubstituted cyclohexane affect its physical properties?

The shape of a molecule can affect its physical properties such as boiling point, melting point, and solubility. In general, cis disubstituted cyclohexanes tend to have lower boiling points and melting points, and are less soluble in polar solvents compared to trans disubstituted cyclohexanes.

5. What are some common examples of cis/trans disubstituted cyclohexanes?

Cis/trans disubstituted cyclohexanes can be found in many organic compounds, including natural products like terpenes and steroids. Some commonly known examples include cis-1,2-dimethylcyclohexane and trans-1,2-dichlorocyclohexane.

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