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Write the mechanism for:

question

I've been able to add part of the product, but am having trouble with the ring formation. Here is my attempt:

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  • $\begingroup$ Have a look at the adjacent methyl groups attached to the bicyclo[2.2.2]octane. Can you spot the pattern in the product? When the free $\ce{OH}$ is esterified, what happens to the bridgehead methoxy group under acidic conditions? $\endgroup$ Feb 19, 2016 at 17:58
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    $\begingroup$ Could come up with uploadable picture? $\endgroup$
    – Mithoron
    Feb 19, 2016 at 18:36
  • $\begingroup$ @klauswarzecha I don't know if you saw my second picture, but I've already added the formic acids to the methyls and etherified the OH, is there any way I can form a ring with that carbocation? Or am I going about it all wrong? $\endgroup$ Feb 19, 2016 at 18:49
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    $\begingroup$ Maybe start by looking up named sigmatropic rearrangements. That should help get you started $\endgroup$
    – Beerhunter
    Feb 19, 2016 at 19:56

2 Answers 2

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I leave the arrows filling and details of last step to you since it is homework and online Marvin JS did not let me do arrows the way I liked to.

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This calligraphy might show you the direction.

enter image description here

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