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Summary Chemical engineering
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HyperconjugationIn chemistry, the term "hyperconjugation" refers to the delocalization of
electrons in a molecule through the overlap of a sigma bond and an
adjacent empty p orbital. This phenomenon occurs in compounds that have
a sigma bond adjacent to a carbon-carbon double bond, a carbonyl group,
or a positive charge. Hyperconjugation can influence the stability and
reactivity of molecules, and it plays an important role in organic chemistry.
One example of hyperconjugation is the stabilization of alkyl cations. When
an alkyl group loses a proton to form a carbocation, the positive charge is
localized on the carbon atom. However, the adjacent carbon-carbon sigma
bond can donate electron density to the empty p orbital of the carbocation,
delocalizing the positive charge and making it more stable. This effect is
known as hyperconjugation stabilization, and it can greatly increase the
stability of carbocations.
Hyperconjugation can also affect the acidity of molecules. For example, in
the case of ethyl acetate, the alpha-hydrogen (the hydrogen atom on the
carbon adjacent to the carbonyl group) is more acidic than other hydrogens
in the molecule. This is because the hyperconjugation effect allows the
adjacent carbon-carbon sigma bond to donate electron density to the
carbonyl group, stabilizing the negative charge that forms on the oxygen
atom when the alpha-hydrogen is deprotonated.
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