1. Not "out of the box".
2. Most of the easily available macro code relies on the ability to automate
the full Outlook. If you do not have Outlook, you would probably have to use
a macro that sent e-mails directly via MAPI or SMTP.
3. How I would approach this would depend on whether I wanted to attach the
same .pdf to every e-mail, or a different .pdf to each e-mail. If it is the
same, it may not be too hard to generate the e-mails via mailmerge, then
manually attach the same .pdf to each e-mail. It depends on how many you
want to send. If it is a different .pdf for each message and you have a lot
of messages, that could be a lot of work, in which case it may be cheaper to
buy the full Outlook or some other software to do it (it depends on how you
cost your time).
If it is /just/ when you "start mail merge from tools menu then the
following may not be enough, but I would start here:
http://tips.pjmsn.me.uk/t0002.htm
Peter Jamieson