Preamble: The following are all of the possible (unordered) hat combinations that could exist for a total of 7, 8, or 9 hats:
22221: 9 hats
22211: 8 hats
22111: 7 hats
TL;DR
The game only completes when the logician with 1 hat is asked first.
In order for 7 hats to be on the logicians heads, none of the logicians can see three 2-hatted logicians. All of the logicians see at least three 2-hatted logicians, so 7 hats is not possible. This leaves the logicians considering only the 8- and 9-hat scenarios.
Case 12222:
$L_1$ sees 8 hats and can immediately deduce "I have one hat on my head."
From the viewpoint of the other logicians, $L_1$ must have seen zero 1-hatted logicians. Had he seen one, $L_1$ would not have enough information to deduce whether this was an 8-hat or 9-hat scenario.
$\therefore L_{2,3,4,5}$ are all able to deduce that they each wear 2 hats and the game completes.
Case 21222:
$L_1$ sees 7 hats. He cannot determine if he has 1 or 2 hats. The table could be arranged as 11222 or 21222 from the perspective of $L_1$.
It is unknown to the logicians at this point that 7 is not a valid hat count. As such, $L_1$ would also not be able to determine if he saw two 1-hatted logicians.
So at this point, $L_{3,4,5}$ see the table as 21x22, 212x2, 2122x respectively, where x is still unknown.
$L_2$ sees 8 hats and can determine that he has 1 hat.
If $L_2$ saw 1 hat on any of $L_{3,4,5}$, he would be unable to deduce that he is wearing 1 hat. It is at this point that $L_{3,4,5}$ know they are each wearing 2 hats.
If $L_2$ saw 1 hat on $L_1$, he would still be able to make his statement, so $L_1$ is not able to guess and the game does not complete.
Case 22122:
$L_1$ sees 7 hats. He cannot determine if he has 1 or 2 hats. The table could be arranged as 12122 or 22122 from the perspective of $L_1$.
From the perspective of $L_{2,4,5}$, the table could additionally be set up as 2x122, 221x2, 2212x respectively.
$L_2$ having no new information cannot make a decision when seeing only one hat.
$L_3$ of course knows that he's wearing 1 hat because he sees 8.
Again, if $L_3$ saw 1 hat on either of $L_{4,5}$, he would be unable to deduce that he is wearing 1 hat. It is at this point that $L_{4,5}$ know they are each wearing 2 hats.
If $L_3$ saw 1 hat on $L_2$, he would still be able to make his statement because he knows $L_2$ was unable to guess (i.e., he knows $L_2$ did not see 8 hats), so $L_2$ is not able to guess and the game does not complete.
Case 22212:
$L_1$ sees 7 hats. He cannot determine if he has 1 or 2 hats. The table could be arranged as 12122 or 22122 from the perspective of $L_1$.
From the perspective of $L_{2,3,5}$, the table could additionally be set up as 2x212, 22x12, 2221x respectively.
$L_2$ having no new information cannot make a decision when seeing only one hat.
$L_3$ having no new information cannot make a decision when seeing only one hat.
$L_4$ of course knows that he's wearing 1 hat because he sees 8.
Again, if $L_4$ saw 1 hat on any of $L_{1,2,5}$, he would be unable to deduce that he is wearing 1 hat. It is at this point that $L_{1,2,5}$ know they are each wearing 2 hats.
If $L_4$ saw 1 hat on $L_3$, he would still be able to make his statement because he knows $L_3$ was unable to guess (i.e., he knows $L_3$ did not see 8 hats), so $L_3$ is not able to guess and the game does not complete.
Case 22221:
$L_1$ sees 7 hats. He cannot determine if he has 1 or 2 hats. The table could be arranged as 12122 or 22122 from the perspective of $L_1$.
From the perspective of $L_{2,3,5}$, the table could additionally be set up as 2x212, 22x12, 2221x respectively.
$L_2$ having no new information cannot make a decision when seeing only one hat.
$L_3$ having no new information cannot make a decision when seeing only one hat.
$L_4$ having no new information cannot make a decision when seeing only one hat.
$L_5$ of course knows that he's wearing 1 hat because he sees 8.
Again, if $L_5$ saw 1 hat on any of $L_{1,2,3}$, he would be unable to deduce that he is wearing 1 hat. It is at this point that $L_{1,2,3}$ know they are each wearing 2 hats.
If $L_5$ saw 1 hat on $L_4$, he would still be able to make his statement because he knows $L_4$ was unable to guess (i.e., he knows $L_4$ did not see 8 hats), so $L_4$ is not able to guess and the game does not complete.