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Test Info:

<!DOCTYPE html>
<html>
<head>
<script>
function boom()
{
window.getSelection().removeAllRanges();
var r = document.createRange();
r.setStart(document.getElementById("x"), 1);
r.setEnd(document.getElementById("y"), 0);
window.getSelection().addRange(r);
document.execCommand("insertorderedlist", false, null);
}
</script>
</head>
<body onload="boom();"><div id="x" contenteditable="true">a</div><div id="y" contenteditable="true"></div></body>
</html>