Does pyridine undergo nucleophilic aromatic substitution reactions? if no, why not. if yes, on what position does the substitution occur? use resonance contributors to justify your answer.(15 points) b) draw the tautomers of 2-hydroxypyridine and 4-hydroxypyridine (5 points)

Explanation:

Part a

Pyridine is an aromatic heterocyclic compound and undergoes nucleophilic aromatic substitution reaction at 2 and 4 positions.

This is because, when a  nucleophile attack pyridine at 2 and 4 positions, the anoin formed is stabilized. In the anion formed is tabilized by resonance and also negative charge is present at electronegative atom, nitrogen.

If the nucleophile attack at 3 position, the anion formed is not as stable as anions formed when nucleophile attach at 2 and 4 positions. This is because negative charge is not present at the nitrogen atom.

Part b:

Tautomers are structural isomers of each others formed by migration atom within the molecule. Tautomers exist in equilibrium with each other.

Tautomers of 2-Hydroxypyridine and 4-Hydroxypyrine are given in the attachment.

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vanderwaal's forces of attraction are the electrostatic intermolecular forces that exist in a molecule due to the temporary or permanent dipoles that are developed in a molecule. in , the major intermolecular forces are dipole-dipole interactions as the molecule is polar (bent structure). so the vanderwaal's forces of interaction in between molecules are the permanent dipole-dipole interactions that develop due to the dipole that exists in between the polar h - s bond. the positively charged hydrogen atom is attracted towards the negative end of the dipole that is sulfur of the adjacent molecule. therefore, these forces of attraction are relatively stronger than that of london dispersion forces that exist in non polar molecules.