Reactive intermediate

In chemistry a reactive intermediate is a short-lived high energy highly reactive organic species. When generated in a chemical reaction it will quickly convert into a more stable molecule. Only in exceptional cases these compounds can be isolated and stored. Reactive intermediates help explain how a chemical reaction takes place.

The main carbon reactive intermediates.

• carbocations
• carbanions
• free radicals
• carbenes

common features

• low concentration with respect to reaction substrate and final reaction product
• with the exception of carbanions, these intermediates do not obey the lewis octet rule hence the high reactivity
• often generated on chemical decomposition of a chemical compound
• it is often possible to prove the existence of this species by spectroscopic means
• cage effects have to be taken into account
• often stabilisation by conjugation
• often difficult to distinguist from a transition state

The other reactive intermediates.

• nitrenes

References

• Carey, Francis A.; Sundberg, Richard J.; (1984). Advanced Organic Chemistry Part A Structure and Mechanisms (2nd ed.). New York N.Y.: Plenum Press. ISBN 0-306-41198-9.
• March Jerry; (1885). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. ISBN 0-471-85472-7