Can a small block timing chain jump a tooth?

To jump a tooth requires a slack chain; find out how much slack you have in your chain. remove your distributor cap, put a ratchet on the crank bolt, start with the damper on "0" slowly rotate the crank until the rotor just starts to move; remember/write down number, rotate the crank back in the opposite direction until rotor just starts to move. That will give you a good idea of how worn your chain is. You are looking for the least amount of crank movement relative to rotor movement.