Is this duplicate content?

[RScime25]

I'm optimizing a Magento site and have a question regarding duplicate content. Currently, you can dig down to an individual product listings with URLs similar to this:

(1) http://www.foo.com/category/sub-category/sub-sub-category/item.html

However, we also have a "Top 50" area, with a link to the same page; however, the URL for that page is:

(2) http://www.foo.com/item.html

Both are dynamic, so a static page for (2) with different content is out of the question. I asked IT to have both (1)  and (2) point to exactly the same page, within the same categor(ies), but they said I would have choose one or the other

So, here are my questions:

1. Will Google consider the pages to be duplicates of each other, and thus incur a penalty;

2. If I were to choose one structure, which would be the "friendliest?"

I've think I've come across questions similar to this in Q&A, but haven't been able to locate them; so, I'm sorry to be posting a "duplicate question." I've been busy writing completely different product descriptions, nice and deep and value-rich, for more than 300 items and categories and am only now starting to look at current SEO protocols; I'm hoping to ask Google for a site reevaluation in another 2 weeks or so.

Thanks.

[csmithal]

I would definitely point the link to #2 (http://www.foo.com/item.html) - because of the directory structure in the URL.

You could NOINDEX http://www.foo.com/category/sub-category/sub-sub-category/item.html with robots.txt.