UBC CHEM ChIRP: Chapter 2 – Exercise Answers (2025)

NOTE: The correct answer(s) for each question are written/drawn in red.

Page 2.9

Complete the table by determining the bond orders and ordering the associated bond lengths and bond
dissociation energies from the choices given below.

• Bond lengths: 1.20 Å, 1.34 Å, 1.54 Å

• Bond dissociation energies: 364 kJ mol–1, 602 kJ mol–1, 835 kJ mol–1

C-C bond order Bond length (Å = 10–10 m) Bond dissociation energy

Ethane 1 1.54 Å 364 kJ mol–1

Ethene 2 1.34 Å 602 kJ mol–1

Ethyne 3 1.20 Å 835 kJ mol–1

Page 2.11
1. Rationalize the trend in bond dissociation energies of C-C bonds (i.e., single, double, triple C-C bonds). Then,
do the same with C-N and C-O bonds.

The trend in bond dissociation energies from the table is that it increases as C-C < C=C < C≡C. As the
bond order increases, more energy is required to break the bond(s) holding the two atoms together. The
same trend is observed for the series of C-N and C-O bonds.

2. Not all double bonds are stronger than all single bonds. Find a counter example in Table 2.2.

The N=N bond (418 kJ mol–1) has a lower dissociation energy than many single bonds, such as H-H
(436 kJ mol–1). There is no simple explanation to rationalize this observation with the knowledge we
have so far in CHEM 111/121/141.

Page 2.15
For the following Lewis structures, determine whether each atom labeled with an asterisk (*) has an octet,
incomplete octet, or is hypervalent.

(a) (c) (e)

(b) (d) (f)

(a) B has an incomplete octet.

(b) Br is hypervalent.
(c) O has an octet; the middle C has an octet; the C on the right (bonded to two hydrogens) has octet.
(d) B has an octet; N has an octet.
(e) N has an incomplete octet; O has an octet.
(f) C has an incomplete octet (it is a radical).

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 UBC CHEM ChIRP: Chapter 2 – Exercise Answers (2025)
Page 2.19
Assign non-zero formal charges to each of the atoms in the following Lewis structures.

(a) tetrahydroborate ion

(b) cyanuric chloride: no formal charges are needed on any atom

(c) nitrate ion

(d) nitrosylazide

Page 2.24
Draw Lewis structures for the following compounds. Write any non-zero formal charges next to the appropriate
atoms, show all lone pairs of electrons as pairs of dots, and all bond pairs as lines.

(a) CO2 (carbon dioxide)

(b) CH3Cl (chloromethane)

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 UBC CHEM ChIRP: Chapter 2 – Exercise Answers (2025)
(c) [NH4]+ (ammonium ion)

(d) PCl3 (phosphorous trichloride)

(e) N2O (nitrous oxide)

According to the rules on ChIRP 2.20 – 2.21, the best Lewis structure for N2O has the negative formal
charge on the more electronegative oxygen (below, left). However, nitrogen is only a little less
electronegative than oxygen, and thus a second, chemically reasonable resonance structure can also be
drawn (below, right). The actual electron distribution in N2O has contributions from both the individual
major (left) and minor (right) Lewis structures.

(f) [BN2H2]– (atom connectivity: H—N—B—N—H)

The octet rule is more important than formal charges in terms of determining relative stabilities of Lewis
structures. Complete the octets on all atoms before reducing formal charges (or optimizing their
placement). Boron is in Group 13 and can be electron deficient, but if it is possible to complete the octet
on B, do it. The electron distribution in the Lewis structure below will be more stable than having an
electron-rich nitrogen atom (with a negative FC) next to an electron-deficient boron atom with an
incomplete octet.

(g) PCl5

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 UBC CHEM ChIRP: Chapter 2 – Exercise Answers (2025)
(h) SF6

Page 2.27
Determine the relationship between each pair of chemical species below. That is, are they resonance structures
or isomers?

(a) (c)

(b) (d)

(a) Isomers
(b) Resonance structures
(c) Resonance structures
(d) Isomers

Pages 2.28 – 2.30

1. One of the two resonance contributors for N-methylacetamide is shown below. Which of the following
resonance forms (A or B) best rationalizes why the carbon-oxygen bond in N-methylacetamide is weaker
than a typical C=O double bond. Is the one that you did not choose chemically reasonable?

Structure A best explains why the carbon-oxygen bond in N-methylacetamide is weaker than a typical
C=O bond. Of the two structures, it is the one where all atoms have a complete octet. For the purpose of
CHEM 111/121/141, structure B is not considered chemically reasonable. When you go on to CHEM 123
and beyond, Structure B may be invoked to explain chemical reactivity of N-methylacetamide and
related species, but it is a minor resonance structure compared to Structure A.
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 UBC CHEM ChIRP: Chapter 2 – Exercise Answers (2025)

2. Draw all the chemically reasonable resonance structures of the following compounds. 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) [C2H3O]–

(b) [C2O4]2– (oxalate ion)

(c) [NO3]– (nitrate ion)

(d) C6H6 (benzene)

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 UBC CHEM ChIRP: Chapter 2 – Exercise Answers (2025)
3. (a) Draw the major resonance structures of the following ion:

The answer is:

(b) Consider the real structure, which is an average of the resonance structures. What is the bond order of
the C-O bond?

(A) 1 (B) 2 (C) 3 (D) Between 1 and 2 (E) Between 2 and 3

The answer is choice D (a bond order between 1 and 2) because the for the original structure, the bond
is a bond bond (bond order of 2) and in the second figure, the bond is a single bond (bond order of 1).
Therefore, since the actual/real structure is a combination of the major resonance structures, the bond
order of the real structure is: (2 + 1) / 2 = 1.5.

Pages 2.35 – 2.36

Draw all chemically reasonable resonance structures for the following species. 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) [ClO3]– (chlorate)

Although the seven structures below are all chemically reasonable resonance structures (i.e., the upper
left one satisfies the octet rule for all atoms), the bottom three are the best resonance structures as
formal charges are minimized.

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 UBC CHEM ChIRP: Chapter 2 – Exercise Answers (2025)
(b) [PO4]3– (phosphate)

(c) XeF2

(d) SO2F2

Page 2.40
Label the atoms in the Lewis structures below with the oxidation states, formal charges, and partial charges.
Note: ion charges are not shown on the templates.

Species Oxidation state(s) Formal charge(s) Partial charge(s)

H3O+ H = +1; O = –2 H = 0; O = +1 H = δ+; O = δ-

CH3OH H = +1; O = –2; C = –2 H = 0; O = 0; C = 0 H = δ+; O = δ-; C ~ 0

NH4Cl H = +1; N = –3; Cl = –1 H = 0; N = +1; Cl = –1 H = δ+; N = δ–;

Cl has a full negative charge

(not a partial charge)