Why Your Lewis Structures Keep Looking Wrong
I spend most of my time grading worksheets where students draw structures that are technically valid but completely miss what the question is actually asking for. The most common error isn't counting electrons wrong - it's that they stop drawing after the first acceptable structure instead of finding the best one, or they create a resonance hybrid when a single dominant structure works just fine.
The process itself is mechanical enough that most people can learn it in an afternoon. The problem is that textbooks present it as if there's one correct path, when really there are about six different failure modes you'll hit depending on the molecule.
Counting valence electrons sounds trivial until you encounter transition metals, polyatomic ions with hypervalent atoms, or compounds where the central atom isn't the least electronegative one. I had a student once draw the structure for ClF3 with chlorine in the middle, which turns out to be correct by accident since chlorine is indeed less electronegative than fluorine, but her reasoning was completely backwards. She'd memorized a rule that doesn't actually hold in most cases.
Approaching Lewis Structure Practice Problems
Here's the actual sequence that works, not the simplified version you see in textbooks:
Write down every atom. Draw single bonds connecting them. Subtract two electrons per bond from your total valence count. Distribute remaining electrons as lone pairs starting with the most electronegative atoms. Check if everyone has an octet. If not, convert lone pairs from adjacent atoms into double or triple bonds until they do.
That's it. The part nobody tells you is step five. You need to check formal charges after you've satisfied the octet rule, because the structure that satisfies the octet rule is sometimes not the best structure.
For example, take the sulfate ion SO4 2-. A naive student will put all single bonds and distribute the charge evenly across all four oxygens. That gives sulfur a formal charge of +2 and each oxygen a formal charge of -1, which sums to the correct -2 overall charge but looks chemically nonsensical. The actual best structure involves two double bonds and two single bonds, putting the formal charges at zero for sulfur and -1 for the singly bonded oxygens. This reduces the charge separation significantly.
The exception to always minimizing formal charge comes with elements in period 3 and below. Sulfur can expand its octet because it has d-orbitals available, though honestly the actual contribution of those d-orbitals to bonding is debated in modern computational chemistry. What matters for your homework is that you're expected to use them.
Common Edge Cases That Break the Standard Algorithm
N3- (azide ion) is where most students get tripped up. The linear structure [N=N=N]2- has a central nitrogen with only 4 electrons if you treat it as two double bonds, or a weird formal charge distribution if you try the standard algorithm. The actual answer is [NN-N]2- with a formal charge of -1 on the terminal nitrogens and 0 on the central one, but some textbooks also accept the resonance form with the negative charge on the central nitrogen. Neither structure is perfect because all three nitrogens want octets and the ion only has 16 valence electrons to work with.
I once spent twenty minutes with a student who was convinced that NO2 was impossible to draw correctly. The issue was that nitrogen dioxide has an odd number of valence electrons (17 total), which means one atom must have an incomplete octet. Most students resist this because they've been told "octet rule is everything." The actual structure has nitrogen as the central atom with one double bond, one single bond, and one unpaired electron on the nitrogen. The formal charges work out to 0 on nitrogen and 0 on the double-bonded oxygen and +1 on the single-bonded oxygen, but you can also draw a resonance form where the single and double bonds swap positions.
Phosphorus pentachloride and sulfur hexafluoride are the other classic trouble spots. Students who've internalized the octet rule too deeply will try to force eight electrons around phosphorus or sulfur and end up with structures that don't match the molecular formula at all. Just remember that period 3 elements and below can accommodate more than eight electrons in their valence shell.
Where Lewis Structures Actually Fail
The biggest limitation nobody emphasizes is that Lewis structures cannot describe bonding in molecules where molecular orbital theory is necessary. This includes ozone (which has delocalized electrons that no single Lewis structure captures), benzene (where resonance is just a workaround for a real delocalization problem), and anything involving paramagnetic properties.
O2 is the textbook example. A Lewis structure predicts all electrons are paired, which would make oxygen diamagnetic. But oxygen is experimentally paramagnetic. The Lewis structure gets the bonding wrong despite looking reasonable on paper. You need MO theory to explain this, and no amount of Lewis Structure Practice Problems will prepare you for that gap.
Transition metal complexes are essentially impossible to draw with Lewis structures in a meaningful way. You might draw coordinate covalent bonds, but the actual d-orbital splitting and bonding interactions require crystal field theory or ligand field theory. Don't waste time trying to force d-block chemistry into Lewis diagrams.
Resources for Lewis Structure Practice Problems
The best practice sets I've found are the ones that include formal charge analysis as a required step, not just drawing. Most online worksheets let you get away with incorrect structures because they only check connectivity. Look for problems that ask you to calculate formal charges for every atom in your final structure.
Khan Academy has a decent section on this topic with video walkthroughs, though their examples tend to avoid the interesting edge cases. For more challenging problems, older editions of textbooks like Zumdahl or Brown/LeMay have excellent problem sets in their chemical bonding chapters. The answers in the back usually include formal charge calculations, which lets you verify your work properly.
University chemistry departments often post practice exams online. These are better than commercial worksheets because professors tend to include at least one "trick" question each semester - usually involving a hypervalent atom or an odd-electron species - that forces you to actually understand the limitations of the method.
I keep a folder of these on my desk. The ones that are most useful are the ones where you can't just look up the answer because the molecule is unusual enough that even reliable sources disagree on the best representation. That's when you learn the difference between knowing the algorithm and understanding what the drawing is actually supposed to communicate.