Tetra-tert-butylethylene

Definition

Tetra-tert-butylethylene is an alkene compound with four tert-butyl groups attached to the carbon-carbon double bond. It is an important molecule in the context of understanding the stability of alkenes.

5 Must Know Facts For Your Next Test

1. The presence of four tert-butyl groups on the carbon-carbon double bond of tetra-tert-butylethylene creates significant steric hindrance, which stabilizes the alkene.
2. The bulky tert-butyl groups prevent the carbon-carbon double bond from undergoing addition reactions, making tetra-tert-butylethylene relatively unreactive.
3. The steric hindrance in tetra-tert-butylethylene also leads to a decrease in the bond angle of the carbon-carbon double bond, further contributing to its stability.
4. Tetra-tert-butylethylene is an example of a highly substituted alkene, where the presence of multiple substituents can have a significant impact on the stability and reactivity of the molecule.
5. The increased stability of tetra-tert-butylethylene due to steric hindrance is an important concept in understanding the factors that influence the stability of alkenes in organic chemistry.

Review Questions

• Explain how the presence of four tert-butyl groups on tetra-tert-butylethylene affects the stability of the alkene.
  • The four tert-butyl groups attached to the carbon-carbon double bond of tetra-tert-butylethylene create significant steric hindrance, which stabilizes the alkene. The bulky tert-butyl substituents prevent the double bond from undergoing addition reactions, making the molecule relatively unreactive. Additionally, the steric hindrance leads to a decrease in the bond angle of the carbon-carbon double bond, further contributing to the overall stability of the tetra-tert-butylethylene molecule.
• Describe the relationship between the degree of substitution and the stability of alkenes, using tetra-tert-butylethylene as an example.
  • The stability of alkenes is influenced by the degree of substitution, and tetra-tert-butylethylene provides a clear example of this principle. As a highly substituted alkene with four tert-butyl groups, tetra-tert-butylethylene exhibits increased stability compared to less substituted alkenes. The presence of the bulky tert-butyl substituents creates significant steric hindrance, which prevents the carbon-carbon double bond from undergoing addition reactions and also leads to a decrease in the bond angle, both of which contribute to the overall stability of the molecule. This demonstrates how the degree of substitution can have a significant impact on the stability of alkenes.
• Analyze how the steric hindrance in tetra-tert-butylethylene affects its reactivity and compare it to the reactivity of less substituted alkenes.
  • The steric hindrance in tetra-tert-butylethylene, caused by the presence of four tert-butyl groups, significantly reduces the molecule's reactivity compared to less substituted alkenes. The bulky tert-butyl substituents prevent the carbon-carbon double bond from undergoing addition reactions, making tetra-tert-butylethylene relatively unreactive. This is in contrast to less substituted alkenes, which are more susceptible to addition reactions due to the lack of such extensive steric hindrance. The decreased reactivity of tetra-tert-butylethylene is a direct consequence of the steric effects introduced by the four tert-butyl groups, highlighting the important role that the degree of substitution plays in determining the stability and reactivity of alkenes.

Related terms

Alkene: An unsaturated hydrocarbon compound containing a carbon-carbon double bond.

Tert-butyl group: A branched alkyl group with three methyl groups attached to a single carbon atom.

Steric Hindrance: The repulsive interaction between bulky substituents that can affect the stability and reactivity of a molecule.