I don't know how to help about jack detection. It doesn't work on my laptop 
(lenovo 3000 N200 hda-intel) as well (and it never did). But I can tell you how 
I successfully made my headphones work again with connector selection option in 
gnome-volume-preferences applet.
Open a terminal and type "cd /usr/share/pulseaudio/alsa-mixer/paths/"
then give a "sudo gedit analog-output-headphones.conf".
Locate "[Element Front]" in gedit and replace
"[Element Front]
switch = off
volume = off"
with:
"[Element Front]
switch = off
volume = merge".
The save, close and reboot. This time connector selection option should work.
---
If it doesn't, please open a terminal and type: "alsamixer", then try setting 
all volumes to high, including front, and all the trigger on (you can toggle a 
trigger by pressing "m"), all but the front trigger which should be set to off.

-- 
Headphones not activated regression (karmic)
https://bugs.launchpad.net/bugs/414746
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