Cycloalkenes

Cycloalkenes are cyclic hydrocarbons that contain at least one carbon–carbon double bond within a ring, making them important substrates for studying alkene reactivity, ring strain, and stereochemistry. Their π bond undergoes electrophilic addition reactions because the electron-rich alkene interacts with electrophiles, while catalytic hydrogenation adds H₂ across the double bond and can convert the cycloalkene into a cycloalkane. Cycloalkenes serve as versatile intermediates in organic synthesis, where oxidation, functionalization, and controlled stereochemical outcomes help build pharmaceuticals, natural products, and advanced materials.

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JoVE Core - Analytical Chemistry

Mass Spectrometry: Cycloalkene Fragmentation

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2024

The molecular ions of cycloalkenes undergo fragmentation via a retro-Diels–Alder reaction. The reaction proceeds via the cleavage of two carbon-carbon bonds in the cycloalkene to yield ethene. The remaining part of the cycloalkene structure is a dienyl radical cation with a molecular weight of 28 u lower than the molecular ion. This fragmentation pathway is similar to the fragmentation of cycloalkanes releasing ethene, differing only in the resultant radical cation. An alkyl species forms from...

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