What is the Difference Between Pyrrolidine and Piperidine?

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Pyrrolidine and piperidine are both organic compounds with cyclic structures, but they have different chemical formulas and ring sizes. The key difference between pyrrolidine and piperidine is:

  • Pyrrolidine: This compound has the chemical formula (CH2)4NH and is also known as tetrahydropyrrole. It contains a five-membered ring. Pyrrolidine is a cyclic amine that can be classified as a saturated heterocycle and occurs as a colorless liquid at room temperature. It is miscible with water and most organic solvents, and it has an ammoniacal and fishy odor.
  • Piperidine: This compound has the chemical formula (CH2)5NH. It contains a six-membered ring. Piperidine is also a cyclic amine, but it has a different ring size compared to pyrrolidine.

Both pyrrolidine and piperidine are non-aromatic, heterocyclic structures, meaning they have no delocalized electron clouds and are saturated compounds. They are used in various industrial applications, such as solvents and chemical intermediates.

Comparative Table: Pyrrolidine vs Piperidine

Pyrrolidine and piperidine are both organic compounds with cyclic structures, but they have some key differences. Here is a table comparing their properties:

Property Pyrrolidine Piperidine
Chemical Formula (CH2)4NH (CH2)5NH
Ring Size Five-membered Six-membered
Classification Saturated Heterocycle Heterocyclic
Occurrence Found in alkaloids like nicotine Not found in alkaloids
Industrial Production Reacting 1,4-butanediol and ammonia at high temperature and in the presence of a nickel oxide catalyst Not applicable
Laboratory Synthesis Reacting 4-chlorobutan-1-amine and a strong base Not applicable

The main difference between pyrrolidine and piperidine is the size of their rings: pyrrolidine contains a five-membered ring, while piperidine contains a six-membered ring. Both compounds are classified as saturated heterocyles, meaning they have no delocalized electron clouds. They are also both found in various industrial applications and can be synthesized in the laboratory.