CameraIcon
CameraIcon
SearchIcon
MyQuestionIcon
MyQuestionIcon
447
You visited us 447 times! Enjoying our articles? Unlock Full Access!
Question

In pyrrole
The electron density is maximum on
1529351_7f3f177d50c14d22b1b5c03f36324819.png

Open in App
Solution

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.

1325419_1529351_ans_2efb11f0180e41abaef0cec12e40cd91.png

flag
Suggest Corrections
thumbs-up
0
Join BYJU'S Learning Program
similar_icon
Related Videos
thumbnail
lock
Introduction
CHEMISTRY
Watch in App
Join BYJU'S Learning Program
CrossIcon