The following transformation involves a carbo | vedclass

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(C) The reaction involves the acid-catalyzed dehydration of a spiro-alcohol. First,the hydroxyl group is protonated to form an oxonium ion,which then

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$c$

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(C) The reaction involves the acid-catalyzed dehydration of a spiro-alcohol. First,the hydroxyl group is protonated to form an oxonium ion,which then loses a molecule of water to generate a secondary carbocation at the carbon atom adjacent to the spiro-center. To expand the five-membered ring into a six-membered ring (forming a decalin-like structure),a ring expansion rearrangement occurs. Specifically,the bond labeled $c$ (a $C$-$C$ bond of the five-membered ring) migrates to the positively charged carbon. This migration converts the five-membered ring into a six-membered ring,resulting in a more stable carbocation,which then undergoes deprotonation to form the final alkene product.

The following transformation involves a carbocation rearrangement. The carbocation is generated by protonation of the hydroxyl group,followed by the loss of water. Which bond has to migrate in the carbocation to yield the product indicated (after the deprotonation)?

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