UBC CHEM ChIRP: Chapter 2 – Additional Problem Questions (2025)
1. Provide values for m and n that would complete the empirical formula of a compound that is isolable. Check
out page 2.3 for the definition of isolable.
(a) KmFn
(b) Mgm[PO4]n
(c) Bam[SO4]n
(d) Mgm[NO2]n
(e) Km[Cr2O7]n
2. Arrange the following atoms (from molecules) in order of increasing electronegativity.
Al, C, Cl, S, Si
3. Which of the following species contains only ionic bonds?
(A) NaN3
(B) CaF2
(C) H2SO4
(D) NH4Cl
(E) Li3PO4
4. Which of the following molecules cannot be represented by a Lewis structure with a complete octet on each
atom?
(A) O2
(B) CO
(C) N2
(D) NO2
(E) N2O
5. Complete the following sentence. When choosing among a set of non-equivalent Lewis structures for a
chemical species, the most favoured is the one:
(A) that contains the greatest number of double bonds.
(B) in which the sum of the formal charges is always zero.
(C) that contains only single bonds.
(D) in which the formal charges on atoms are as low as possible.
(E) in which the central atom always has positive formal charge.
6. Which of the following would not be expected to exist as an isolable molecule?
(A) NH3
(B) N2H6
(C) SF4
(D) N2H4
(E) None of the above.
7. Which of the following pairs of molecules or ions are isoelectronic? Isoelectronic species have the same total
number of electrons.
(A) N2 and O2
(B) [SCN]– and [OCN]–
(C) [NO3]– and [CO3]2–
(D) OF2 and OH2
(E) CO and NO
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UBC CHEM ChIRP: Chapter 2 – Additional Problem Questions (2025)
8. Draw the best Lewis structure(s) for each of the following molecules or ions. Write any non-zero formal
charges on the appropriate atoms, show all lone pairs of electrons as pairs of dots, and all bond pairs as
lines.
(a) H2S
(b) BCl3
(c) HN3 (atom connectivity is H—N—N—H)
(d) COH2 (formaldehyde)
(e) [BH4]–
(f) [IO2F2]–
(g) [CN]– (cyanide ion)
(h) SCl4
(i) [BrO3]–
(j) SO3
9. The C-O bond order for the carbonate anion, [CO3]2–, wherein C is the central atom, is best described as:
(A) between 0 and 1
(B) exactly 1
(C) between 1 and 2
(D) exactly 2
(E) between 2 and 3
10. Which of the following molecules or ions contain a triple bond?
(A) [O2]2+
(B) C2HCl (chloroacetylene) (atom connectivity H—C—C—Cl)
(C) [O2]2–
(D) CO
(E) [NO]+
11. Draw a Lewis structure for NO2 and use it to explain why NO2 may be toxic.
12. Draw the best Lewis structure for HNCO. The atom connectivity is H—N—C—O. Write any non-zero formal
charges on the appropriate atoms, show all lone pairs of electrons as pairs of dots, and all bond pairs as
lines.
13. Draw Lewis structures for the best two isomers of S2F2. Write any non-zero formal charges on the
appropriate atoms, show all lone pairs of electrons as pairs of dots, and all bond pairs as lines.
14. Which of the following species have resonance structures? For each, show all of the chemically reasonable
resonance structures. Show all lone pairs as pairs of dots and show any non-zero formal charges.
(a) OF2
(b) [NO3]–
(c) O3
(d) [OH]–
15. Draw all chemically reasonable resonance Lewis diagrams for the two ions given below. For each diagram,
write the formal charge on each atom. Indicate the diagram that best represents the bonding in the ion, and
write the reason for making your particular choice.
(a) [ClO4]– (chlorine is the central atom)
(b) [SCN]– (carbon is the central atom)
16. Draw Lewis structures for three possible isomers with the molecular formula NOBr (none of which contain
rings). Given that NOBr is formed from the reaction of bromine with nitric oxide, give the most likely structure
for NOBr.
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UBC CHEM ChIRP: Chapter 2 – Additional Problem Questions (2025)
17. For each skeletal structure below, complete the Lewis structure by adding bonds, lone pairs, and formal
charges where appropriate. Draw all chemically reasonable resonance structures.
(a)
(b)
(c)
(d)
(e)
(f)
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UBC CHEM ChIRP: Chapter 2 – Additional Problem Questions (2025)
(g)
(h)
(i)
18. Draw Lewis structures for the TWO BEST resonance forms of the following species. Write any non-zero
formal charges on the appropriate atoms. Show all lone pairs of electrons as pairs of dots.
(a) [OCN]–
(b) N2O3 (the atom connectivity is in this molecule)
19. For each of the ions below, draw the best three resonance structures. For each structure, write any non-zero
formal charges on the appropriate atoms. In each case, the central atom is underlined. Show all lone pairs as
pairs of dots.
(a) [ClO2]–
(b) [CN2]2–
20. Classify the following pair of structures as (A) isomers or (B) resonance structures.
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UBC CHEM ChIRP: Chapter 2 – Additional Problem Questions (2025)
21. The molecule nicotine is an addictive substance found in tobacco. The skeletal structure of nicotine is shown
below. Multiple bonds and lone pairs are not shown. Use this structure to answer questions a and b.
(a) In nicotine, the C-C bond labelled “W” is expected to be:
(A) the same length as a typical C-C bond.
(B) between the length of a typical C-C single and double bond.
(C) the same length as a typical C-C double bond.
(D) between the length of a typical C-C double and triple bond.
(E) the same length as a typical C-C triple bond.
(b) In nicotine, the C-C bond labelled “X” is expected to be:
(A) the same length as a typical C-C bond.
(B) between the length of a typical C-C single and double bond.
(C) the same length as a typical C-C double bond.
(D) between the length of a typical C-C double and triple bond.
(E) the same length as a typical C-C triple bond.
22. How many double bonds are present in the best Lewis structure of chloric acid, HClO3?
23. The N-O bond length in [NO]+ is 106 pm and the N-O bond length in NO2 is 124 pm. What is the N-O bond
length in [NO2]+?
(A) 106 pm
(B) 124 pm
(C) 90 pm
(D) 140 pm
(E) 115 pm
24. (a) Draw the 3 most chemically reasonable Lewis structures for a furanolate anion, [C4H3O2]–, using the
skeletal structures below. Show all lone pairs of electrons as pairs of dots and all additional bonds as lines.
Write any non-zero formal charges on the appropriate atoms.
(b) Select the best Lewis structure above.
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UBC CHEM ChIRP: Chapter 2 – Additional Problem Questions (2025)
25. Draw the 4 best resonance Lewis structure for the squarate anion, [C4O4]2–, by neatly completing the skeletal
structures below. Show all lone pairs of electrons as pairs of dots and all additional bonds as lines. Write any
non-zero formal charges on the appropriate atoms.
26. The compound dinitrogen pentoxide, formula N2O5, exists in two isomeric forms.
(a) In the solid state, dinitrogen pentoxide is found as the ionic compound [NO2]+[NO3]–. Draw the best
resonance structure of [NO2]+. Show all lone pairs as pairs of dots and all bonds as lines. Write any non-
zero formal charges on the appropriate atoms.
(b) In the gas phase and in solution, dinitrogen pentoxide is found as the molecule N2O5 with connectivity
shown on the template below. Draw the four best resonance structures for N2O5. Show all lone pairs as
pairs of dots and all bonds as lines. Write any non-zero formal charges on the appropriate atoms.