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Q. What is the major product in the following reaction?
$C_{6}H_{5} — CH = CH — CH_{3} \xrightarrow[{H_{2}O}]{ (i)(CH_{3}COO)_{2}Hg }\,\xrightarrow[H_{3}O^{+}] {(ii)NaBH_{4} }$

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Solution:

In oxymercuration-demercuration reaction, Markownikoff's addition of $H_{2}O$ takes place with $HO^{-}$ added to carbon which can bear +ve charge of bridge cation