I have not had the problem, but you can repath the icon if it cannot be found. Right click on the icon, click properties and then FIND TARGET. Go to acad.exe. To find it, do a search for acad.exe. It should be in something like C:\Program Files\ACAD2000 (something like this usually).
If you cannot find acad.exe, you will need to reinstall it.
Here is a fix from Autodesk for file association problems:
Open Windows Explorer.
On the Tools menu, click Folder Options.
In the Folder Options dialog box, click the File Types tab.
Scroll down the list of file extensions to DWG and select it.
Click Advanced.
In the Edit File Type dialog box, under Actions, select Open.
Click Edit to open the Editing Action for type dialog box.
In the Application used to perform action box, the path to the acad.exe or the aclt.exe file is displayed.
The following text should be at the end of the path in this box:
"%1"
If %1 is not in quotation marks ("%1", the error message is displayed when DWG files are opened from Windows Explorer.
Add quotation marks around the %1 ("%1".
Make sure the Application box in this dialog box is either blank, or has the value acad (for AutoCAD® software or products based on AutoCAD) or aclt (for AutoCAD LT® software).
Click OK in each dialog box to accept the changes and close the dialog boxes.
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