Hello, Ed. All of these have a 1/4" pilot. The gear head diameters are considerably different. The smallest one, ( L-shaped key) stamped S-80 , seems too small for a 1/2" chuck. The largest one, is unmarked. 2nd from left is stamped Jacobs 7 and K7. 3rd from left is stamped S #2. Maybe someone on here recognizes these markings. I will look around for a 1/2" chuck, (although there are many variations) to see if one of these keys fit. Regards, Lou