The correct answer is 3) Worcester vs. Georgia
The McCulloch vs. Maryland case dealt with the idea of implied powers and interpretation of the US Constitution.
Loving vs. Virginia was a Supreme Court case that struck down state laws against individuals from a different race not being able to get married. This makes interacial marriages all over the US legal.
Worcester vs. Georgia was a Supreme Court case that established the idea that only the federal government has the authority to conduct deals with Native American tribes.
This shows why option 3 is the only correct answer.