[jonnyfive]

Hi everyone,

I'm having a terrible time with this mechanism. I just can't see it for some reason. How does this work? I think the first step is probably the SN1 of the OH, but I just can't see how the ring would magically expand.

The reactant and product can be seen in the attached JPEG file.

Thank you SO much!

[azmanam]

forget that for a second... can you draw the mechanism for this reaction?

[Dolphinsiu]

Here is the suggested mechanism. You can take it as reference.

[azmanam]

dude...

[azmanam]

well... so this is a variant of the pinacol rearrangement.

http://www.cem.msu.edu/~reusch/VirtTxtJml/rearrang.htm#top2

[jonnyfive]

Wow. Thank you so much everyone. I didn't realize it would be so simple. I forgot all about carbocation rearrangements. I guess it's been a while since first semester organic! Thank you again.