# What will be the final product when the above bridged compound is heated with concentrated sulfuric acid?

What will be the final product when the above compound ((1S,2S,4R,7S)-7-methylbicyclo[2.2.1]heptane-2,7-diol) is heated with concentrated sulfuric acid?

I know that the hydroxyl group in the bridgehead position cannot be protonated and removed to form a carbocation. The other hydroxyl group may be protonated and removed to form a carbocation I suppose. But after that what rearrangements will take place ? What will be the final product(s)?

• There isn't any bridgehead hydroxyl in your compound. Dec 29, 2016 at 7:45
• Please have a look at 2-norbornyl cation and/or search for non-classical cation on this site. Dec 29, 2016 at 7:48
• @orthocresol I meant the OH on the top of the compound (in digram). That cannot be removed by protonation as a positive charge will be left behind on a non-planar center. Dec 29, 2016 at 7:49
• Why can't that carbon be planar? It's not a bridgehead, it's a bridge. Dec 29, 2016 at 7:53
• I fail to see why elimination from the tertiary alcohol should not be possible. The resulting cation could either add a nucleophile, which would result in the epimerization of that centre, or undergo elimination. The latter would yield an exomethylene group. Dec 29, 2016 at 7:53

Protonation of both $\ce{OH}$ groups and subsequent formation of the corresponding cations is possible.
• The "secondary" non-classical cation leads to a $\ce{C=C}$ double bond in the ring. With other words, a norbornene is formed.