2.3.2 · D3Chemical Bonding

Worked examples — Formal charge calculation — best resonance structure

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Before anything, recall the three letters — each is a counting task you do by looking at the drawn structure:


The scenario matrix

Here is the full space of cases this topic throws. Each worked example below is tagged with the cell(s) it covers.

# Case class What makes it tricky Example
C1 All-neutral (charge 0, all FC = 0) The "ideal" — confirms the tool Ex 1 (CH₄)
C2 Positive FC present (cation) Sum must be , place on least electronegative Ex 2 (H₃O⁺)
C3 Negative FC present (anion) Sum must be charge, place on most electronegative Ex 3 (OH⁻)
C4 Competing resonance forms tie Use electronegativity tie-breaker Ex 4 (OCN⁻)
C5 Magnitude ±2 vs ±1 Smaller magnitude wins Ex 5 (ozone O₃)
C6 Expanded octet / degenerate "more bonds" More bonds can lower FC below period-3 atoms Ex 6 (SO₄²⁻)
C7 Zero / degenerate input ( or ) A lone ion, a bare atom Ex 7 (Na⁺, Cl⁻)
C8 Real-world word problem Translate a sentence into a structure Ex 8 (nitrogen dioxide smell)
C9 Exam twist / isoelectronic Same electrons, "which is real?" Ex 9 (N₂ vs CO⁻ trap)

Ex 1 — CH₄ (Cell C1: all-neutral)

  1. Carbon. (group 14). Lone pairs? None on C, so . Four single bonds → . Why this step? C keeps half of its 8 bonding electrons (= 4), exactly matching its valence → neutral.
  2. Each Hydrogen. (group 1). . One single bond → . Why this step? H brought 1 electron, keeps half of its one bond (= 1) → neutral.

Verify: checksum , matches CH₄'s neutral charge. ✔


Ex 2 — H₃O⁺ (Cell C2: positive FC, cation)

  1. Oxygen. (group 16). One LP → . Three single bonds → . Why this step? O normally makes 2 bonds with 2 lone pairs. Here it made a third bond, giving away a lone-pair electron's worth of ownership → it comes up one electron short → .
  2. Each Hydrogen. , , one bond → . Why this step? H keeps half of its single bond (= 1), matching its valence → neutral.

Verify: checksum , matches the ion's charge. ✔ On the placement rule: the arithmetic forces the onto O. Rule 4 ("put on the least electronegative atom") is a tie-breaker between structures, not a licence to move a charge arbitrarily — here only one structure is sensible, so arithmetic wins.


Ex 3 — OH⁻ (Cell C3: negative FC, anion)

  1. Oxygen. . Three LP → . One single bond → . Why this step? O now owns 6 lone-pair electrons plus 1 shared = 7, one more than its valence 6 → excess electron → .
  2. Hydrogen. , , . Why this step? H keeps half of its one bond (= 1), matching its valence → neutral.

Verify: checksum . ✔ And by Rule 3 the negative sits on O, the more electronegative atom — consistent with reality.


Ex 4 — OCN⁻ cyanate (Cell C4: resonance tie, electronegativity decides)

Valence: O=6, C=4, N=5.

  1. Form A.
    • O (, double bond → ): Why this step? O owns 4 lone-pair + 2 shared = 6, exactly its valence → neutral.
    • C (, two double bonds → ): Why this step? C keeps half of 8 shared electrons (= 4) = its valence → neutral.
    • N (, double bond → ): Why this step? N owns 4 lone-pair + 2 shared = 6, one more than its valence 5 → .
  2. Form B.
    • O (, triple bond → ): Why this step? O made a third bond and shed a lone pair, so it owns only 5 → one short → .
    • C (, four bonds → ): Why this step? Same as Form A — C keeps 4 = its valence → neutral.
    • N (, single bond → ): Why this step? N owns 6 lone-pair + 1 shared = 7, two more than valence 5 → .
  3. Compare. Form A has one nonzero FC of magnitude 1; Form B has magnitudes 1 and 2. Rule 1 (fewer charges) and Rule 2 (smaller magnitudes) already kill Form B before we even reach electronegativity.

Verify: checksum Form A ✔; Form B ✔. Both are valid Lewis pictures but Form A is far superior. (Interesting twist: the best cyanate form actually puts the on N, not O — because putting it on O would force the awkward Form B geometry. So Rule 3 bows to Rule 2 first: the ranking order matters!)


Ex 5 — Ozone O₃ (Cell C5: ±1 present, geometry figure)

The figure below shows the bent molecule: the central oxygen (drawn in plum) sits at the top vertex, the double-bonded terminal oxygen (orange, joined by a two-line double bond) is at the lower left, and the single-bonded terminal oxygen (teal, joined by one line) is at the lower right. Each atom carries a labelled call-out giving its bond/lone-pair count and its resulting formal charge, and the box underneath restates the checksum.

Figure — Formal charge calculation — best resonance structure
  1. Central O (1 LP → ; one double + one single bond → ). Why this step? The central atom makes three bonds total — one more than oxygen "wants" — so it is a bond richer and an electron poorer → . This is the plum atom at the top of the figure.
  2. Double-bonded terminal O (2 LP → ; double bond → ). Why this step? It owns 4 lone-pair + 2 shared = 6 = its valence → neutral (the orange atom, lower left).
  3. Single-bonded terminal O (3 LP → ; single bond → ). Why this step? Only one bond and three lone pairs → owns 7 electrons, one too many → (the teal atom, lower right).

Verify: checksum , matches neutral O₃. ✔ Neither terminal ever reaches ±2, so no better all-zero structure exists — the charges are forced by the double bond having to sit on one side. Both resonance forms (double bond left vs right) are equally good — that's why ozone resonates.


Ex 6 — Sulfate SO₄²⁻ (Cell C6: expanded octet lowers FC)

Valence: S=6, O=6.

  1. Form X — Sulfur (four single bonds → , ): Why this step? S with only single bonds keeps just 4 shared electrons, two fewer than its valence 6 → . Each O (single bond → , 3 LP → ): . Why this step? Each O owns 6 lone-pair + 1 shared = 7, one more than valence 6 → .
  2. Form Y — Sulfur (two double + two single → , ): Why this step? Two extra bonds let S "own" more shared electrons (6), dropping its FC from all the way to . This is allowed because S is period 3 and can hold more than 8 electrons (expanded octet). Double-bonded O (, ): . Why this step? Owns 4 lone-pair + 2 shared = 6 = valence → neutral. Single-bonded O (, ): . Why this step? Owns 6 lone-pair + 1 shared = 7, one more than valence → .
  3. Compare. Form X: charges and four (five charged atoms). Form Y: two atoms at , everything else zero. Fewer charges (Rule 1) and smaller magnitudes (Rule 2) → Form Y wins.

Verify: Form X checksum ✔. Form Y checksum ✔. Both equal the ion's ; Form Y is the major contributor.


Ex 7 — Na⁺ and Cl⁻ (Cell C7: degenerate inputs, )

  1. Na⁺. Free Na has . As Na⁺ it has lost its valence electron, so it has no lone pairs and no bonds: , . Why this step? This is the degenerate case: no bonds means FC = valence electrons brought minus lone electrons kept. Na kept nothing of its one electron → .
  2. Cl⁻. Free Cl has . Chloride gained one electron → 8 electrons, all as four lone pairs (4 LP): , . Why this step? It owns 8, brought 7, so it has one extra → .

Verify: FC of a bare ion equals its actual ionic charge — the formula degrades gracefully to the obvious answer. ✔, ✔.


Ex 8 — NO₂ word problem (Cell C8: real-world)

  1. Nitrogen. . It has one unpaired electron → (a single electron still counts as one non-bonding electron). One double + one single bond → . Why this step? The lone single electron contributes only 1 to , not 2 — this is the trap. N still ends up electron-poor → .
  2. Double-bonded O (, ): . Why this step? Owns 4 lone-pair + 2 shared = 6 = valence → neutral.
  3. Single-bonded O (, ): . Why this step? Owns 6 lone-pair + 1 shared = 7, one more than valence → .

Verify: checksum , matching neutral NO₂. ✔ By Rules 3–4 the sits on the less-electronegative N and on the more-electronegative O — exactly what the placement rules prefer, so this structure is real. That unpaired electron makes NO₂ a reactive radical.


Ex 9 — Isoelectronic trap: CO vs the "N₂" reflex (Cell C9: exam twist)

  1. N₂ check. Each N: , one LP → , triple bond → : . Symmetric → both zero. Why this step? Identical atoms split identically → no charge separation.
  2. CO — Carbon (, , ): . Why this step? C brought only 4 valence electrons but owns 2 lone-pair + 3 shared = 5, one extra → .
  3. CO — Oxygen (, , ): . Why this step? Same bonding pattern as N₂, but O brought 6 and owns only 5 → one short → . Electron count matches N₂; electron ownership vs valence does not.

Verify: N₂ checksum ✔. CO checksum ✔, matching neutral CO. So the student is false: isoelectronic species share electron totals, not formal charges. (The odd on the less-electronegative carbon is exactly why CO is such a reactive, unusual gas — consistent with Worked Example 2 in the parent.)


Recall

Recall Which ranking rule beats which?

Order: (1) fewest nonzero FCs → (2) smallest magnitudes → (3) negative on most electronegative → (4) positive on least electronegative → (5) checksum must hold. Rules 1–2 come before electronegativity — that's why Ex 4 and Ex 6 were decided by magnitude, not by which atom is more electronegative.

Recall The degenerate case

For a bare ion with no bonds (): FC , which just equals the actual ionic charge. The formula never breaks.

Recall The odd-electron trap

A single unpaired electron counts as , not . (See NO₂, Ex 8.)


Connections

  • Parent topic — this page drills every case of it.
  • Lewis Structures — every example starts from a drawn Lewis diagram.
  • Resonance Structures — Ex 4, 5, 6 are all "which resonance form wins?" cases.
  • Electronegativity — the tie-breaker used in Ex 4 and placement in Ex 8, 9.
  • Oxidation Number — contrast: FC splits bonds evenly; oxidation number gives them all to the electronegative atom.
  • Octet Rule — Ex 6 shows S breaking the octet to lower its FC (expanded octet).
  • VSEPR Theory — the winning structure (bent O₃, bent NO₂) then feeds shape prediction.