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I AM UNABLE TO UNDERSTAND THIS QUESTION . HELP ME TO ITS ANSWER

I AM UNABLE TO UNDERSTAND THIS QUESTION .  HELP ME TO ITS ANSWER

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Grade:12th pass

1 Answers

Arun
25758 Points
3 years ago
Pyrrole has maximum electron density on 2 and 5. It generally reacts with electrophiles at the C-2 or C-5 due to the highest degree of stability of the protonated intermediate. Attack at position 3 or 4 yields a carbocation that is a hybrid of structures (I) and (II). Attack at position 2 or 5 yields a carbocation that is a hybrid not only of structures (III) and (IV) (analogous to I and II) but also of structure (V). The extra stabilization conferred by (V) makes this ion the more stable one.  Also, attack at position 2 or 5 is faster because the developing positive charge is accommodated by three atoms of the ring instead of by only two.

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