You can use the drag function to return the position of the draggable element while it's being moved. Compare that against the position of the outer edge of the parent and when the two intersect trigger the resizing action.
This fiddle is a very simplified version of what you're looking for, but it should illustrate the basic concept and get you started in the right direction. Hopefully this helps.
$(function(){
var draggableRight;
var draggableWidth = $('.draggable').width();
var parentWidth = $('#parent').width();
$('.draggable').draggable({
containment: 'parent',
drag: function(e, ui){
draggableRight = ui.position.left + draggableWidth;
if(draggableRight == parentWidth){
$(document).trigger("mouseup");
$('.draggable').css({
width: '50%',
height: '100%',
top: 0,
left: '50%'
});
}
}
});
});