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Question

How is the following transformation best carried out?

225726_39b67f781f9346a0a5473783c0d07222.png

A
BH3THF;H2O/NaOH
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B
O3;Zn/AcOH
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C
HgSO4/H2SO4/H2O
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D
OsO4;NaHSO3
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Solution

The correct option is C HgSO4/H2SO4/H2O
Hydroboration of terminal dialkynes produces enols by anti-markovnikoff's addition which rearrange to produce dialdehyde.
Ozonolysis produces dicarboxylic acid and CO2 by oxidative cleavage.
Oxymecuration also produces enol by markovnikoff's addition which rearranges to produce diketone product. Therefore, the given transformation can be carried out by this reaction.
Alkynes do not react with OsO4.

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