Cycloheptatriene

Cycloheptatriene is a chemical compound with the formula C7H8. This hydrocarbon is a colourless liquid that is used as a precursor to other organic compounds. It is not aromatic, as the molecule is not planar.

Structure and synthesis

Cycloheptatriene is not planar and the pi electrons are not delocalized, so it does not exhibit the stability and special reactivity characteristic of aromatic compounds. The molecule adopts a "tub" conformation.

Cycloheptatriene can be prepared by the organic synthesis of cycloheptanone with phosphorus pentachloride (PCl5).

Reactions

Cycloheptatriene is a reactive compound that can undergo a variety of chemical reactions. It can be hydrogenated to give cycloheptane and it can be oxidized using potassium permanganate to give cycloheptanone. It also reacts with bromine to give a mixture of 1-bromocycloheptatriene and 1,4-dibromocycloheptatriene.

Uses

Cycloheptatriene is used as a precursor to other organic compounds. It is also used in research to study the properties and reactions of non-aromatic cyclic compounds.

Safety

Like many hydrocarbons, cycloheptatriene is flammable. It can cause irritation to the skin and eyes, and may be harmful if inhaled or swallowed.

See also

• Cycloalkene
• Cycloheptane
• Aromaticity