Note: they all seem odd to me because of the use of 'across' rather than 'through', but, that aside, the following are definitely incorrect: 4 and 8
So the others are conceivably correct but many are strange/awkward. For instance, 12 and 13 are grammatically correct but it's difficult to conceive of a situation where they could occur logically speaking. 1 is correct as long as 'drawing' is a noun here. 2 assumes there is more than one Tom and you are distinguishing which. 3 is inelegant in the extreme. etc.