The boot deteriorates (just like any rubber part) over time and develops cracks. Also, the clamps might be a bit flaky so I would suggest you get a new pair of clamps along with the boot. I saved quite a bit on the "Junkyard Dawg" by ordering these items from Moto-Bins.
Synthetic doesn't actually make things leak but it is more likely to illuminate marginal gaskets and seals by being slipperier and a better cleaner than dino oil. I have read (long, long ago) that crud and varnish can build up on shafts using dino oil and actually form a "dam" at the seal/shaft interface thus helping a marginal seal do it's job. After changing to synthetic this "crud dam" can be dissolved resulting in the marginal seal not being up to the task. Usually switching back to dino will "fix" the leak, as long as it wasn't much more than a "seep", due to the dino stuff not being as slippery...