A small sample of the liquid mash (no solid particles) is placed on a white porcelain saucer. A few drops of tincture of iodine are added. Watch the interface between the two, looking for any change in color. When iodine meets starch or other more complex carbohydrates,* it will turn black, blue, deep mahogany, etc. depending on the degree to which the carbohydrates have been broken down. Black or blue indicates a lot of native starch. No color change at all, the dilute iodine still showing a yellowish color, indicates complete conversion, all the starch turned to sugars. This is called a "negative iodine test" and is your goal. At this point you can mash off and collect the wort. You can, I say. But conversion is not the same as extraction:
Tracking density is easiest with a refractometer on our scale. You can calculate the maximum wort density possible given your grain bill and volume of water, and when that is reached you know you have not only converted starch to sugar, but fully extracted it into the wort. That probably is a topic for elsewhere, but both of these are discussed on the old Braukaiser website (though Kai has a rather wonkier version of the iodine test.)
*Including cellulose and the like, which is why you want to avoid solid particles of grain and husk in the sample.
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