Give the best reaction sequence to prepare the above compound:

B r H - --- \to R O O R L i - \to C u l / C H_{3} C H_{2} C H_{2} l - ---------- \to

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C l H - --- \to R O O R L i - \to C u l / C H_{3} C H_{2} C H_{2} l - ---------- \to

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Dicyclohexylborane - ---------- \to C H_{3} C H_{2} C H_{2} L i H_{3} O^{+} - -- \to

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H g S O_{4}, H_{2} S O_{4} - -------- \to C H_{3} C H_{2} C H_{2} L i - --------- \to H_{3} O^{+}

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Solution

The correct option is B $B r H - --- \to R O O R L i - \to C u l / C H_{3} C H_{2} C H_{2} l - ---------- \to$

The best reaction sequence is as shown. The first step is the addition of a molecule of $H B r$ to Carbon-Carbon triple bond in the presence of peroxide. $B r$ is added to terminal C atom. Next step is $C - C$ bond formation with $1 - i o d o p r o p a n e$ in the presence of $L i / C u I$ .

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