$1 - p e n t y n e$ $⟶$ $4 - m e t h y l o c t - 5 - y n - 4 - o l$
Give the best reaction sequence that would accomplish the above conversion:

(C y c l o h e x y l)_{2} B H ⟶ H_{2} O_{2}, O H^{-} ⟶ C H_{3} C H_{2} C \equiv C M g B r, H^{+} / H_{2} O

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H g S O_{4}, H_{2} S O_{4} ⟶ C H_{3} C H_{2} C \equiv C H, H^{+} / H_{2} O

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H g S O_{4}, H_{2} O_{4} ⟶ C H_{3} C H_{2} C \equiv C M g B r ⟶ H^{+} / H_{2} O

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(C y c l o h e x y l)_{2} B H ⟶ H_{2} O_{2}, O H^{-} ⟶ C H_{3} C H_{2} C \equiv C H, H^{+} / H_{2} O

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Solution

The correct option is C $H g S O_{4}, H_{2} O_{4} ⟶ C H_{3} C H_{2} C \equiv C M g B r ⟶ H^{+} / H_{2} O$
The best reaction sequence that would accomplish the given conversion is given by option C. First step is oxymercuration demercuration of terminal alkyne to form ketone. In the next step, grignard reagent attacks ketone, followed by hydrolysis to form tert alcohol.

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C H_{3} C H_{2} C \equiv C H (i) N a N H_{2}, N H_{3} - --------- \to (i i) C H_{3} C H_{2} B r H_{2} - ------------ \to L i n d l a r^{'} s c a t a l y s t, P d C H_{2} I_{2} - --- \to Z n (C u)

F e (C N)_{6}^{x -} + H_{2} O_{2} + H^{+} \to F e (C N)_{6}^{y -} + H_{2} O

[F e (C N_{6})]^{p -} + H_{2} O_{2} + O H^{-} \to [F e (C N_{6})]^{q -} + O_{2} + H_{2} O

Decomposition of H₂O₂yields:

H_{2} O ⟶ H^{+} + O H^{-}

C H_{3} C O O H + O H^{-} ⇋ C H_{3} C O O^{-} + H_{2} O + q_{1}

H^{+} + O H^{-} ⇋ H_{2} O + q_{2}

C H_{3} C O O H ⇋ C H_{3} C O O^{-} + H^{+}

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