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I am confused as to why this molecule changes its structure.
Also, I am confused why instead of OH, CHO is attached.

I would have thought that the double bond would break and OH would attach at each end via syn addition.

The example:

enter image description here

Shouldn't this be the answer? enter image description here

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    $\begingroup$ The molecule changed its structure because the oxidation snapped the whole double bond (like, for example, ozonolysis would) and not just one component of it. How that came possible is another story. $\endgroup$ – Ivan Neretin Apr 17 '16 at 9:10
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    $\begingroup$ I think this is a typo. The sodium periodate (NaIO4) should be included. $\endgroup$ – jerepierre Apr 17 '16 at 14:18

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