If you write too many bad checks then yes you can go to jail for the writing of those bad checks.
If you accidentally wrote the check and thought you had enough funds to cover the check you wrote and only did it a few times in a year or so then you won't go to jail for the bad checks.
You'll just be charged an overdraft charge and have to pay the check and bank back and possibly pay the business a returned check fee which could cost $50.00
Try to make sure you balance your check books often to avoid writing the bad check because if you write too many bad checks in a short amount of time then you could face some jail time.
If you write a check with no money in your bank account to cover the cost of that written check then the check would bounce and you would get an overdraft charge.
So yes you could write the check to someone without the money in the checking account but the check would not clear the bank.
If you wrote the check to a place such as Walmart and the checking account had no money in it then the check would not go through there machine.
So you would not be able to make the purchases with the check without the funds.
If you write the check to a business and mail it to them then you would get an overdraft charge on your checking account and the bill etc still would not be paid.
Then if you continue to write bad checks with no money in the account you could be prosecuted for writing bad checks.