What would be the best method to bring about the following conversion?
$C H_{3} - C H_{3} | C | C H_{3} - C H = C H_{2} ⟶ C H_{3} - C H_{3} | C | C H_{3} - C | H O H C H_{3}$

B H_{3}, T H F;

then

H_{2} O_{2}, O H^{-}

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H B r;

then

N a O H / H_{2} O,

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Conc.

H_{2} S O_{4},

then

H_{2} O

, heat

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H g (O A c)_{2} / T H F - H_{2} O,

then

N a B H_{4}, O H^{-}

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Solution

The correct option is D $H g (O A c)_{2} / T H F - H_{2} O,$ then $N a B H_{4}, O H^{-}$
$3, 3 - d i m e t h y l - 1 - b u t e n e$ reacts with $H g (O A c)_{2} / T H F + H_{2} O$ and $N a B H_{4}, O H^{-}$ to form $3, 3 - d i m e t h y l 2 - b u t a n o l$ .
This is the best method for production of $3, 3 - d i m e t h y l 2 - b u t a n o l$ .
Oximercuration-demercuration reaction brings about markownikoff's hydration of alkene without rearrangement takes place.
$C H_{3} C (C H_{3})_{2} C H = C H_{2} + H g (O A c)_{2} / T H F + H_{2} O N a B H_{4}, O H^{-} - ------- \to C H_{3} C (C H_{3})_{2} C H_{2} O H C H_{3}$
$3, 3 - d i m e t h y l - 1 - b u t e n e$ $3, 3 - d i m e t h y l 2 - b u t a n o l$
So the answer is D.

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