Consider the above synthesis. What is wrong with this transformation?

B H_{3}

is actually unreactive towards alkyne.

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B H_{3}

should add to adjacent carbon rather than the same carbon.

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Boron can be used as an electrophile only with non-terminal alkyne.

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The borane addition follows regiochemistry opposite to that shown.

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Solution

The correct option is C The borane addition follows regiochemistry opposite to that shown.
In the given synthesis, the borane addition follows regiochemistry opposite to that shown. In the product -OH group should be added to terminal C atom which will given an aldehdye and not a ketone. This reaction follows anti-markovnikov's rule. The corrected reaction sequence is as shown.

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Which of the following compound would yield trialkyl borane as shown below when treated with $B H_{3}$ and THF ?

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