Fluoroalkanes, and Zaitsev's rule

Thread starter Kitrak
Start date Feb 23, 2015

AI Thread Summary

In β-elimination reactions involving haloalkanes and bases like KOH, Saytzeff's rule typically predicts that the more substituted alkene will be the major product. However, when fluorine is the leaving group, the reaction yields the less substituted alkene as the major product. This deviation from the expected outcome is attributed to the unique properties of fluorine, which affects the stability of the transition state and the overall reaction pathway. The presence of fluorine leads to a stronger bond and a more significant energy barrier for the formation of the more substituted alkene, resulting in the preference for the less substituted product.

Feb 23, 2015

Kitrak

When haloalkanes undergo a β-elimination reaction with a base, say KOH, usually Saytzeff's (or Zaitsev's) rule is applied and the more substituted alkene is the major product. However, if the halogen group involved is flourine, the opposite happens: the less substituted alkene is the major product. Why does this happen?

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Feb 23, 2015

Raghav Gupta

See this thread we had a discussion there.

Feb 23, 2015

Kitrak

Thanks!

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