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That's how I proceeded with the question. However the answer is tert-butylbenzene. I can't figure out why do I have an extra carbon atom.

SOURCE
- JEE Advanced 1994

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  • 3
    $\begingroup$ Yes, your mechanism seems quite correct. I believe it must be a printing error $\endgroup$ Jan 18 '19 at 13:07
  • $\begingroup$ I agree. No way can you get t-Bu Benzene from this sytem. $\endgroup$
    – Waylander
    Jan 18 '19 at 13:39
  • $\begingroup$ I feel like dehydration of the alcohol is going to be much more likely under the forcing conditions whereby you might actually generate that primary cation... $\endgroup$
    – Zhe
    Jan 18 '19 at 16:39
  • 2
    $\begingroup$ Benzene, the nucleophile, attacks the alcohol - as the cation - which is the electrophile. ;) $\endgroup$
    – user55119
    Jan 22 '19 at 23:42
  • $\begingroup$ The original question doesn't have an extra carbon. $\endgroup$
    – Iceberry
    Feb 18 '19 at 8:06

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