1. Draw the resonance structures obtained by delocalising the lone pair on heteroatom X onto the heteroaromatic ring. Why cannot the lone pair on nitrogen be delocalised on the ring as well? H

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Solve Q1 and 2 with detailed explanation

1. Draw the resonance structures obtained by delocalising the lone pair on heteroatom X
onto the heteroaromatic ring. Why cannot the lone pair on nitrogen be delocalised on the
ring as well?
-N':
H.
2. Compare the pka of pyrrole and imidazole. Which heterocycle is more basic? Applying the
Hückel rule of aromaticity, can you explain this difference in reactivity?
Protonated pyrrole (2): pka = -3.8
н н
H
+ H*
H.
H `H
2
Protonated imidazole (4): pka = 7.0
H
+ H*
H
3
Transcribed Image Text:1. Draw the resonance structures obtained by delocalising the lone pair on heteroatom X onto the heteroaromatic ring. Why cannot the lone pair on nitrogen be delocalised on the ring as well? -N': H. 2. Compare the pka of pyrrole and imidazole. Which heterocycle is more basic? Applying the Hückel rule of aromaticity, can you explain this difference in reactivity? Protonated pyrrole (2): pka = -3.8 н н H + H* H. H `H 2 Protonated imidazole (4): pka = 7.0 H + H* H 3
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