Creating .pdf file from images organized in chronological order

I have many sets of old scanned .TIFF files pertaining to corresponding documents that I would like to get organized into .pdf files. The problem is that these files were given random names when they were scanned into a proprietary database. However they were scanned in order and have time and date stamps corresponding to that order. I have tried organizing them in chronological order in Windows Explorer and then dragging and dropping them on to Acrobat 8. However Acrobat only seems to want to place them in alphabetical order after which I have to go through and tediously put them into the proper order. Is there a way to load them chronologically? I have tried looking through documentation and looking for such an option but I can't find it.
Any help would be greatly appreciated.
Thanks in advance for your help!

Sorry Im totally new to acrobat so this may seem like a daft question> I have scanned a document through a document feed scanner into a pdf format but some of the pages are orientated the wrong way within the pdf, is there a way to change the direction of pages and then save the whole pdf again so that everything is the right way round. I know that you can change the orintation while reading the pdf but as this is being put into web ct for students I would prefer for them not to have to do this.

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