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Question

Which is the best combination of reagent for the reaction?
224206_b3903d6df7e7414fb179fcd7fb630eae.png

A
KMnO4, H3O+
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B
mCPBA, CH2Cl2
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C
(i) 9BBN (ii)NaOH, H2O2
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D
(i) Hg(OAc)2, H2O (ii) NaBH4
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Solution

The correct option is D (i) Hg(OAc)2, H2O (ii) NaBH4
The Oxymercuration reaction is an electrophilic organic reaction that transforms an alkene into a neutral alcohol by addition of water molecule.The oxymercuration reaction is almost always treated with sodium borohydride (NaBH4) in an aqueous base in a reaction called demercuration.

Normally carbocation is formed above which leads to ring expansion. But if we use oxymercuration-dermercuration. Carbocation is not formed
in this process and thus rearrangements are not observed. The reaction follows Markovnikov's rule (the hydroxy group will always be added to the more substituted carbon) and it is an anti addition (the two groups will be trans to each other).

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