Learn English – “Can I” vs “May I” in restaurant setting when ordering

They are all grammatical. Merriam-Webster gives three definitions of graduate in connection with schools.

transitive verb:
1 a : to grant an academic degree or diploma to
1 b : to be graduated from
intransitive verb:
1 : to receive an academic degree or diploma

If you are talking about a single student, the intransitive verb—"He will graduate in May" or "He is going to graduate in May"—is what is generally used.

Your second sentence: "He will be graduated in May," is the passive of *"X University will graduate him in May," using definition 1a (transitive). This sentence sounds strange to me because people usually use the intransitive in the active voice rather than the transitive in the passive voice (unless they have a good reason to use the transitive). However, "X University will be graduating 5,000 students in May" sounds perfectly fine. And you can come up with situations where the transitive in passive voice sounds fine with a single student, for example, "We will not be graduating Bob this year, but Ray will be graduated in May."

Definition 1b (transitive) appears in constructions like "I graduated MIT in 2009." This construction sounds informal to me, possibly because it become popular only after I learned English. I don't see any reason not to use "from MIT".

Google Ngrams shows that the transitive (1a) in passive voice was commonly formerly used for this, but is now rare, and that the popularity of (1b) is growing. However, the intransitive is generally what is currently used.

I am not going to go into the difference between going to and will in this answer; this difference has been hashed out several times on EL&U. For this sentence, both constructions are fine. The likelihood of graduation is the same for both constructions, and I consider them both acceptable in formal letters.

The easy answer is, no. None of the first sentences are correct, except for the first sentence in the first set.

This I have seen and heard regularly. The rest of the sets, numbers 2 and 3 are correct.

Edited: 11 December, 9:25pm EST

I have searched and searched, but have not found a single source that will allow for any wiggle room under the Most High Law of Subject-Verb Agreement. There is never considered a subject, so the subject is, of course, the collection of objects on the table, and regardless of how they are listed, it is a plural subject. I have no grammatical foot to stand on, hence Newton's Law of Universal Gravitation applies.

However, in usage, I will plead my case to Psycholinguistics, wherein research has generated theories in abundance about the architecture and mechanisms of sentence comprehension. At what point in reading does information become available to the reader? Issues such as "modular" versus "interactive" processing have caused heated theoretical rifts in the field.

Sentences are read in separate modules with which the reader interacts. but which have limited interaction with each other. While I generally hold to an interactive theory of sentence processing, in this case I am admitting that the modules are not playing well together at all. In an effort to avoid tedious squabbling, one grabs hold of the first module and deals with its behavior, whilst allowing the others to run amok. Admittedly this is poor parenting on the whole, but what's a person to do? One can listen to the cacophony only so long before becoming overwhelmed.

I place some of the blame on the misbehaving modules. Perhaps it is genetic, as a module does not come into a sentence as a tabula rasa. If the modules would cooperate and line up nicely, there would be little problem.

I summarize that the allocation of attention and the misbehavior of the modules makes this an impossible situation, one that defies the Most High Law. I throw myself on the mercy of the Court.

John Q Public is the Judge.