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Question

Which of the reagents shown below would accomplish the following transformations?
(A)(B)
1) H3O+BH3THF;H2O2/NaOH
2) NaOHBH3THF;H2O2/NaOH
3) HBr in etherHg(OAc)2/H2O;NaBH4
4) NaNH2Hg(OAc)2/H2O2;NaBH4

78212_94ef7e2c649d419eb75c5251199b56da.png

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Solution

In the given reaction first elimination reaction of the compound takes place with NaNH2 to form propene.
This propene is then reacted with Hg(OAc)2/H2O;NaBH4. It undergoes oxymercuration-demercuration reaction to form isopropyl alcohol as a major product.

1147801_78212_ans_d284e8dc49904d1089b2c2ac7ac5cfe2.png

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