Conformation Stability of Ethane-1,2-Diol

This is what makes it more stable overall.In summary, the conversation discusses the concept of torsional strain and how it is affected by the presence of hydrogen bonding in alcohol groups. It is explained that the hydrogen bonding helps to overcome the steric repulsion in the gauche conformation, making it more stable than the anti conformation.
  • #1
EnricoHendro
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Homework Statement
Conformational studies on ethane-1,2-diol (HOCH2-CH2OH) have shown the most stable conformation about the central C-C bond to be the gauche conformation, which is 9.6kJ/mol more stable than the anti conformation. Explain the curious result.
Relevant Equations
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Hello there,
My attempted explanation/solution is :
“Torsional strain is caused by the tendency of the electron clouds in the interacting groups to repel each other, making it relatively difficult to rotate a group towards and through another group, as the repulsive force provides resistance to the rotation. However, in alcohol groups, we have H-O bond. This means that the alcohol groups in ethane-1,2-diol can form hydrogen bonds with each other, and therefore “pulling” one another towards each other (since intermolecular force is an attractive force). This hydrogen bond is stronger when ethane-1,2-diol is in gauche conformation, since both OH groups are closer than in anti. In a sense, it is easier to rotate the compound in gauche conformation due to the help from the Hydrogen Bond. This explains why gauche conformation of Ethane-1,2-diol is more stable than anti conformation.”

Is my attempted explanation correct?
 
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  • #2
Sounds fine. More concise would simply be that the hydrogen bonding overcomes the steric repulsion in the gauche configuration.
 
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FAQ: Conformation Stability of Ethane-1,2-Diol

1. What is the significance of studying the conformation stability of ethane-1,2-diol?

The conformation stability of ethane-1,2-diol is important because it affects the physical and chemical properties of the molecule, which can have implications in various fields such as pharmaceuticals, materials science, and biochemistry.

2. How is the conformation stability of ethane-1,2-diol determined?

The conformation stability of ethane-1,2-diol can be determined through computational methods, such as molecular modeling and quantum mechanics calculations, as well as experimental techniques like nuclear magnetic resonance (NMR) spectroscopy.

3. What factors affect the conformation stability of ethane-1,2-diol?

The conformation stability of ethane-1,2-diol is influenced by factors such as steric hindrance, hydrogen bonding, and van der Waals interactions. The presence of substituents on the molecule can also impact its stability.

4. How does the conformation stability of ethane-1,2-diol relate to its physical properties?

The conformation stability of ethane-1,2-diol can affect its boiling point, melting point, and solubility in different solvents. This is because different conformations have different intermolecular forces and molecular arrangements, which can alter the molecule's physical properties.

5. What are the potential applications of understanding the conformation stability of ethane-1,2-diol?

Knowledge of the conformation stability of ethane-1,2-diol can aid in the design and development of new drugs, materials, and biochemical processes. It can also provide insights into the behavior of similar molecules and contribute to our understanding of chemical bonding and molecular interactions.

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