Question:

Pyridine is less basic than triethylamine because

Updated On: Aug 15, 2022
  • pyridine has aromatic character
  • nitrogen in pyridine is $sp^2$ hybridised
  • pyridine is a cyclic system
  • in pyridine, lone pair of nitrogen is delocalised
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The Correct Option is A

Solution and Explanation

Both pyridine and triethyl amine are $t$-amines triethyl amine is highly basic (gaseous or non polar medium) due to $+I$ effect of $- C _{2} H _{5}$ which increase electron density on $N$ atom. Whereas in pyridine electron density on $N$ atom is less due to resonance.
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Concepts Used:

Amines

Amine is a type of compound which is derived from ammonia (NH3). According to Organic chemistry, they are basically classified as the functional groups of the organic nitrogen compounds that contain nitrogen atoms with a lone pair.

Amine - Types

Primary Amines:

It is formed when one hydrogen atom in ammonia is substituted by an alkyl or aromatic group. Amino acids and methyl amine are the best examples that why aromatic amines include aniline.

Secondary Amines:

Amines that have two organic substitutes either alkyl or aryl ones or both and are bound to the nitrogen together with one hydrogen are termed as secondary amines. For Example, Dimethylamine.

Tertiary Amines:

Tertiary Amines are the amines where the nitrogen consists of three organic substitutes. For example, Trimethylamine and EDTA.