jmc

Of the digits 1 through 5, three are odd and two are even. If Jason's combination started with an odd digit, there would be 3 possibilities for the first digit. Since an even digit must follow, there would be 2 possibilities for the second digit. Similarly, there would be 3 possibilities for the third digit, and so on. This would be a total of: $$3\times 2\times 3\times 2\times 3=108$$We can apply the same logic if Jason's combination started with an even digit. There would be 2 possibilities for the first digit, 3 for the second digit, and so on, for a total of : $$2\times 3\times 2\times 3\times 2=72$$Overall, Jason must try $72+108=\boxed{180}$ combinations.