Question:

on mercuration-demercuration produces the major product:

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Oxymercuration-demercuration is a Markovnikov hydration of the alkene without rearrangement.
Updated On: Nov 11, 2026
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The Correct Option is A

Solution and Explanation

The substrate is allylbenzene, \(\mathrm{C_6H_5-CH_2-CH=CH_2}\).
Oxymercuration (\(\mathrm{Hg(OAc)_2, H_2O}\)) followed by demercuration (\(\mathrm{NaBH_4}\)) adds \(\mathrm{H}\) and \(\mathrm{OH}\) across the double bond following Markovnikov's rule: OH goes to the more substituted carbon (the internal \(\mathrm{CH}\)).
Product: \(\mathrm{C_6H_5-CH_2-CH(OH)-CH_3}\) (1-phenylpropan-2-ol), which is option (1).
Option (2) is the anti-Markovnikov (hydroboration) product; (3) is a diol (needs \(\mathrm{OsO_4}\)/cold \(\mathrm{KMnO_4}\)); (4) needs strong oxidative cleavage.
Answer: (1) \(\mathrm{C_6H_5CH_2CH(OH)CH_3}\)
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