Question

Which alkene in each pair is more stable?

   Which alkene in each pair is more stable?

Organic Chemistry

Organic Chemistry

Janice Gorzynski… 4th Edition

Chapter 8, Problem 6

Instant Answer

Solved by Expert Prashant Singh

05/06/2019

Step 1

The more substituted the carbon atoms involved in the double bond are, the more stable the alkene is. This is because the alkene can distribute the energy lost off the bond over more atoms, making it more stable. Show more…

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Which alkene in each pair is more stable?

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Key Concepts

Heat of Hydrogenation

Heat of hydrogenation is an experimental measure of alkene stability, indicating the amount of energy released upon hydrogenation. Alkenes that release less heat upon hydrogenation are generally more stable because they are closer in energy to the saturated product.

Steric Hindrance

Steric hindrance refers to the repulsive interactions that occur when atoms are brought too close to each other. In the context of alkene stability, increased steric hindrance between substituents can lead to a less stable molecule, making it an important factor to consider when comparing the stabilities of different alkenes.

Hyperconjugation

Hyperconjugation is the stabilization that results when electrons in a sigma bond (typically C–H or C–C) interact with an adjacent empty or partially filled p-orbital or a pi-orbital. This delocalization of electrons spreads out the electron density, thereby stabilizing the alkene, especially when more alkyl substituents are present.

Alkene Substitution

This concept refers to the number of alkyl groups attached directly to the sp2 hybridized carbons in the double bond. More substituted alkenes are generally more stable due to the electron-donating effects of alkyl groups, which help to stabilize the electron-rich double bond.

Cis-trans Isomerism

Cis-trans isomerism in alkenes describes the spatial orientation of substituents around the double bond. The isomers often have different stabilities, with trans isomers typically being more stable than cis isomers because they minimize steric crowding between bulky groups.

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