Pyridine is less basic than triethylamine because:a)Pyridine has aromatic characterb)Nitrogen in pyridine is sp2hybridized.c)Pyridine has a cyclic system.d)Lone pair of nitrogen in pyridine is delocalized.Correct answer is option 'D'. Can you explain this answer?

Question

Answer

Basicity of amines is due to availability of an unshared pair (lone pair) of electrons on nitrogen. This lone pair of electrons is available for the formation of a new bond with a proton or Lewis acid. Pyridine is less basic than triethylamine because lone pair of nitrogen in pyridine is delocalised.

Answer

Because there is unshered election

Answer

Answer is d due to delocalised unshared electron pair

Answer

Pyridine, is much less basic than typical aliphatic amines, but for a very different reason: the unshared pair is in an sp2 , which is much lower in energy than the electron pair of aliphatic amines, which is in an sp3 . Therefore, pyridine is less easily protonated than typical aliphatic amines such as triethylamine .

Answer

Delocalization of Lone pair in Pyridine
Pyridine is less basic than triethylamine because the lone pair of nitrogen in pyridine is delocalized.

Explanation:

1. Delocalization of lone pair:
In pyridine, the lone pair of electrons on the nitrogen atom is delocalized over the entire aromatic ring. This delocalization stabilizes the lone pair by spreading it out over a larger area, making it less available for donation. As a result, the nitrogen atom in pyridine is less likely to act as a strong base compared to triethylamine, where the lone pair is localized on the nitrogen atom.

2. Aromatic character:
While pyridine does have aromatic character due to its cyclic structure and conjugated pi electrons, this factor alone does not significantly impact its basicity compared to the delocalization of the lone pair.

3. SP2 hybridization:
The SP2 hybridization of the nitrogen atom in pyridine does contribute to its planar structure and aromaticity, but it is not the primary reason for its lower basicity.

4. Cyclic system:
The presence of a cyclic system in pyridine does provide additional stability, but again, it is not the main factor affecting its basicity.
In conclusion, the delocalization of the lone pair in pyridine is the key reason for its lower basicity compared to triethylamine. This delocalization results in a decreased availability of the lone pair for donation, making pyridine a weaker base.

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