DAT DAT Question of the Day: Benzylic Cation Boundaries | DAT Destroyer | OAT Destroyer

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Boyuan Zhang takes iodomethylbenzene and reacts it in a solution of 25% water and 75% methanol.
The intermediate will display delocalization of the positive charge over which boundaries?


a) Ortho
b) Ortho and meta
c) Ortho, meta, and para
d) Ipso only
e) None of these


Correct Answer: E


Explanation:
This reaction forms a benzylic cation. The positive charge is stabilized ortho and para to the substituent, but not in the patterns suggested by the answer choices. Therefore, the correct selection is E.


Reference (University of Texas benzyl cation overview):
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