It depends on the level of the class.
I would expect someone who has a recent undergraduate degree in mathematics to have experienced significant figures at at least some point in their life, either in high school or in college. I would also expect common sense to kick in and say that the level of accuracy proposed is unreasonable.
But it is reasonable to dodge the topic when teaching arithmetic, algebra, etc., because the students usually have a hard enough time as it is. Sometimes you can arrange for numbers that come out evenly anyway, but if you're stuck trying to teach an awkward conversion (miles to km) or if the task is to teach something about decimals or fractions then you may be unable to avoid it.
For example, "Alex had five cookies and split them evenly with Blake. How many did each of them get?" Two and a half, and we aren't going to quibble over how precisely half of a cookie was achieved.
If your students are advanced enough to be working with more precise numbers (and, presumably, starting to question what level of accuracy is acceptable) then the best way to dodge it is to simply specify what rounding you want in the question: "Answer to x decimal places." That way you can specify the correct precision without the students having to understand how to calculate what the correct precision should be.
That's much simpler for the student to understand than the official way, which is according to NIST:
The precision of your conversion should be based on relative error. If error isn't specified, then you can infer it from the number of digits in the values given. Use a conversion factor with equal or more precision to that to preform the calculation. Then you round the result to produce a relative error that is of the order of the original.
$22$ miles implies an error range of plus or minus $\frac{1}{2}$ mile which is $2.\overline{27}\%$.
Using a conversion factor of $1.61$ kilometers per mile (which has better than $2.\overline{27}\%$ accuracy, note that $1.6$ is not accurate enough)... $22*1.61=35.42$ km. We could also use $1.609$ or any more precise conversion, it does not matter because we will be rounding. (For example, in this case, $22*1.609 = 35.398$ km.)
Now we round... $40$ km would have a relative error $5\div40\approx12.5\%$ which is too much, $35.4$ would have a relative error of $0.05\div35.4\approx0.141%$ which is too little. $35$ km has a relative error of $0.5\div35\approx 1.43\%$ which is just right. Note that we get the same (rounded) answer regardless of how much precision we used in the conversion factor, as long as the conversion factor met a minimum level precision.
Question: Why do we assume plus or minus one-half mile? Wouldn't a distance of 22 miles be measured more accurately than that?
Answer: No. If anything it is likely to be much worse. (Disclaimer, I'm not doing sigfigs in this section, I just can't be bothered.)
In American revolutionary war era from the New York Public Library, Thomas Jefferson measuring exactly 22 miles would have actually gone over 22.3 miles (and he was a bit obsessive about measurements):
Before he left on the trip, Jefferson bought from a Philadelphia watchmaker an odometer that counted the revolution’s of his carriage’s wheel. He had measured distance based “on the belief that the wheel of the Phaeton [his carriage] made exactly 360. revoln’s in a mile.” After the trip, though, he re-measured circumference of the wheel and found that it made only 354.95 revolutions in a mile. So for every seventy-one miles Jefferson thought he traveled, he had actually traveled seventy-two.
But I use my car odometer, not a carriage! It's much more reliable! ...nope. From motus.com, if your car odometer says 22 miles then it could be anywhere between 21.12 to 22.88 miles:
Surprisingly, there is no federal law that regulates odometer accuracy. The Society of Automotive Engineers set guidelines that allow for a margin of error of plus or minus four percent.
Actually I use GPS, that's very accurate! ....nope again. GPS has a margin of error on every position measurement made, plus error from the distance between measurements. Essentially your path is like a coastline and the GPS can suffer from the coastline paradox. From singletracks.com (with pictures and a good explanation: In a very, very bad case (steep trail, lots of switchbacks) your GPS may report 22 miles when you've actually gone 44 miles! Holy guacamole.
[...]GPS reports the full loop is right at 1 mile long. In fact, everyone else who rides this trail gets roughly the same measurement. But the trail always “feels” much longer than that.
Recently I started riding with a wheel-based cyclocomputer, which I calibrated and verified during one of our track tests. Measuring this particular trail with the cyclocomputer reveals the trail is actually closers to 2 miles long, meaning our GPS units are underestimating distance by half!
I'm not going to find sources for inaccuracy of distance calculated by counting steps, the time it took to travel, etc. It's pretty obvious that no one (and no horse) actually moves at that even of a pace for 22 miles.
So accepting 22 miles on a trail as being between 21.5 and 22.5 is actually pretty generous. Better to just call it a day and say it was "some distance".