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Hydrocarbons question

2016 · Q113
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Hydrocarbons question

2016 · Q113

NEETChemistryHydrocarbonsMCQ+4 / −1
In pyrrole the electron density is maximum on
NEET 2016 Phase 2 Chemistry - Hydrocarbons Question 58 English
  1. A
    2 and 3
  2. B
    3 and 4
  3. C
    2 and 4
  4. D
    2 and 5
View written solutionFree

Correct answer: D

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.

NEET 2016 Phase 2 Chemistry - Hydrocarbons Question 58 English Explanation


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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