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| 1. |
Write resonance-contributing structures for the intermedicate carbocation (arenonium ion) of (i) Phenol (ii) Nitrobenzene with electrophile CI^(o+) at the a. ortho-, b. para-, and c. meta-positions. |
Answer» Solution :i. Activing group [e.g., (-OH)` group] stabilies all `o`-positons more than `m`-postions, since the most stable `3^(@)C^(o+)` is formed when the incoming ELECTROPHILE `(Cl^(o+))` enters at `o-` and `p`-positon.ltbrlt II. Deactivatinggroup [eg., `(-NO_(2))` group] destlises all the positons, but does it with `o-` and `p-` positions more than `m`-position, since one resonance-contriburing structure is LEAST stable (DUE to the POSITIVE charges onadjacent `C` and `N`) when incomingelectrophilic `(Cl^(o+))` enters at `o-` and `p`-position. Hence electrophile attacks at `m-` positions. |
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