If I deliver a change set to a stream and not associate it with a work item can the change set be associated with a work item after it has been delivered ?
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Yes.
The changeset itself is closed upon delivery to the stream.
But its associated work-item(s) is not: you can add or remove one or several work-items in association with the delivered changeset.
That being said, I have a special hook which makes that association mandatory on deliver: ie, you cannot deliver without having first associated your change set first to a Work Item.
I am not sure if that hook is a custom one for my organization, but here is where you can check if it is there:
It is in the Project Area administration, under
Team Configuration /
Operation Behavior /
Source Control /
Deliver (client) /
Preconditions and follow-up actions are configured for this operation /
Require Work Items and comments

VonC
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thanks, I like the idea of a hook for force the association. Is this difficult to setup, can you add a link on how to do this ? – blue-sky Nov 13 '12 at 14:11
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1@user470184 I have edited my answer to add and illustrate the hook. – VonC Nov 13 '12 at 14:31