How is the following transformation best carried out?
A
BH3−THF;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 CHgSO4/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.