Lewis Structures, Formal Charge, and Oxidation

Numbers
A More User-Friendly Approach
John E. Packer and Sheila D. Woodgate
University of Auckland, Private Bag, Auckland, New Zealand

Two articles emphasizing difficulties experienced by stu-

dents in writine Lewis structures have recentlv aooeared in
this journal (1,-2). Pardo (1) correctly pointedoit'that one
reason for these difficulties is that few elementary textbooks
give a simple set of rules for doing so. He identified the main
oroblems encountered. T h e second article (2) based on an
i sstudent errors on drawing Lewis structures on a
k n a ~ ~ sof
comouter confirmed that Pardo's identification of problem
areas was essentially correct. The substance of ~ a r d o ' sarti-
cle had been to give a set of rules designed to overcome these
difficulties. ~ n c o r t u n a t e lhe
~ , appeared not to have seen the
excellent article by Snadden (3) or read the appropriate
section on Gillesoie's well-known North American text ( 4 ) .
These authors present essentially the same rules more sim-
olv. A small New Zealand txmk (5) whose authors had inde.
p&dently followed the snadden and Gillespie approach
adopts a still more "user-friendly" manner. In this article
this "user-friendly" approach is outlined with three exam-
ples and compared with the Snadden, Gillespie, and Pardo
methods hopefully demonstrating that if students follow a
set of rules faithfully, the difficulties classified by Brady e t
al. (2)should not arise.
Rules for Drawing Lewls Structures
(a) Determine the total number of valence electrons in the species
by adding together the numbers of valence electrons of each
atom and, if an anion, by adding the overall charge of the ion
and, if a cation, by subtracting the overall charge of the ion.
(b) Place the atoms in their relative positions.
(c) Draw a line representing a single bond containing two eleetrona
between joined atoms.
(d) Distribute the remaining electrons evenly in pairs on the outer
atoms so these have up to eight electrons (except for hydrogen).
Any still not used after this should be placed on the central
atom.
(e) If the central atom is now surrounded by fewer tban eight
electrons, move sufficient nonbonding pairs from outer atoms Figure 1. Examplesoftheapplicationoftherulesfor drawing Lewis structures.
other tban halogens to between joined atoms, thusmaking them
bonding, t o bring the number on the central atom up to a
maximum of eight.
( f ) Count the number of electrons "owned" by each atom pretend- la. Rule (e) leads to multiple bonds, and rule (g) allows for
ing bonding electrons are evenly shared. To evaluate the formal the fact that elements of the second and later rows of the
charge at that atom, compare the result with the number of
valence electrons of the neutral atom. Show only nonzero periodic table can have more than eight valence electrons (d
charges. electrons), but there is no mention of either of these more
(g) For central atoms from the second or later rows of the periodic ..
advanced conceots in the actual rules. This aooroach also
table, move further nonbonding pairs to bonding positions to requires minimal arithmetic and provided students f o l l ~ w
lower the positive formal charge on the central atom to one or t h m faithfully
. thev. will nlwavs oroducea valid Lewis strut-
zero. ture. Furthermore, rule (g) allows students toobtain the best
Three examples for C0s2-, N01, and SOz, are given in Figure representative Lewis structure. In the case of SO2 this rule
1. leads to the structure 2 rather than the commonly given
structure 1. Very recently in this Journal Purser has argued
Discussion of Rules cogently the case for the superiority of structure 2 (5).
These rules require no chemical knowledge other than the Snadden's first step is the same as rules (b) and (c). His
number of valence electrons of atoms (i.e., elementary atom- second step, "Count up the number of bonding electrons and
ic structure) and which atoms are joined together. The latter subtract from the total number of valency electrone provid-
information must he given as fact a t the time Lewis struc- ed by the individual atoms or ions. The difference gives the
tures are first introduced if i t is not obvious from the formu- number of electrons which must be accommodated in the

456 Journal of Chemical Education

 structure either as non-bonding lone nairs or additional
bonding pairs," could he too much for some students. His
third sten is in essence the same as (c) and (d) but reauires
more arithmetic. His fourth and fifth steps &e essenkally
the same as (e). Our rule (f) for determiningformal charge by
electron counting is much less formidable than the equation
given by Snaddenand many textbooks: "Formal charge of an
atom in a molecule = number of valency electrons in the
unhonded atom - (half the numher of shared electrons + were under the beading "central atom skills" and had to do
number of non-bonding electrons)".
Gillespie's rules are perhaps closer to those given here
than are Snadden's. However, his rule corresponding to our
(d) puts the electrons on the more electronegatiue atoms
rather than the outer ones, requiringa concept not necessary
a t this stage. He assigns formal charge hefore moving elec-
tron oairs to comolete an octet around the central atom.
effeciively reversing the order of our (e) and (f) but does not
includeinstructionsun how todo this within his Lewisstruc-
ture rules. He determines formal charge in the same way as
Snadden hut uies core charge, a further concept, or group
number, no longer ronsistent with the 1I:PAC periodic tahlc
format, instead of "number of valencs electrons in the un-
bonded atom."
Inspection of Pardo's steps ( I ) show that they are more
complex still. He requires calculation of the number of
bonding electrons by determining the numher of valence
electrons individual atoms would have and subtracting the
numher of valence electrons actually available. Then the
numher of a electrons are determined from the structure.
and the numher of T electrons calculated from the difference
between the totalnumber of bonding electrons and the num-
ber of a electrons. All this is unnecessary to ohtain a correct
structure, and in most courses simple Lewis structures
would be met before the more sophisticated concept of a and
a honds is introduced.
If the skill of writing Lewis structures has been mastered
a t an early age by practice using a set of simple rules, the
rationale of the rules and the inadequacies of a single Lewis
structure can he introduced later a t the appropriate time.
Thus the moving of electrons to minimize formal charge
illustrates the well-known fact that it requires energy to
separate unlike charge, and species spontaneously tend to-
ward adopting a state of minimum energy. A single Lewis
structure of COa2- implies that one C-0 bond is different
from the other two, whereas physical measurements show all
the honds are the same. Thus the "real" structure may be
represented by all three possihle Lewis structures each mak-
ing an equal contribution, i.e., the simple representation of
resonance. Early in most courses students meet the equilib-
rium 2N02 + N204 with the implication the hond in the
dimer must be weak. The Lewis structure of NzO4,3, shows
two positive charges close together implying that formal
charge is a physically meaningful concept.
3
" Whereas most textbooks fail to "
The rules for writing Lewis structures suggested in this
paper and by Snadden and Gillespie start with the assump-
tion the students know which atoms are ioined toeether in
the species. By applying the rules and arriving a t a Lewis
structure showing the distribution of valence electrons, it is a
simple further step to predict the actual shape by assuming
that honds (sinale or multiole), nonhondine electron pairs.
and single unpaired electrons represent electron clouds that
adopt a geometry to keep as far away from each other as
possihle to minimize the energy of the species, i.e., the va-
lence-shell electron pair repulsion (VSEPR) theory of Ny-
holm and Gillespie.
In their article "Lewis structure skills: taxonomy and dif-
ficulty levels" Brady et al. (2) identified 12 individual skills
that they perceive students require to do all the 51 examples
given to them and determined the difficulty of each skill (on
a four-point scale) from the success or failure rate of the
students. The students had had one lecture on drawing Lew-
is structures and had done some homework but bad not
practiced long enough to become adept. Three of these skills
with student difficulty in identifying the central atom from
the given formulas, such as FN02, SCN-, POC13, S Z O ~ ~ - .
This is hardly a Lewis structure skill hut something more
sophisticated, and i t would he unreasonable to expect stu-
dents to predict the arrangement of atoms in such species a t
the time they should first meet Lewis structure writing. In
fact, one can write perfectly valid structures for different
possihle isomers of all the ahove species, e.g., 4 and 5 for
POC13. In a recent national examination in New Zealand
students were asked to draw a Lewis structure of ozone. 09.
being told only that i t was a nonlinear molecule. About 30%
eave structure 6. a nerfectlv valid answer that received full
marks in view of tKe fact that they were not told the hond
angle was greater than 60'.
Six other of the perceived skills were classified as "adjust-
ment skills" and were called: odd (i.e., odd numher of elec-
trons.. e.e..
- . NO. Clog): nromote he.. multinle honds. ex..
NO3-, C02); tr&l <i.'e:, no multiple bond; or nonhdnded
electrons on central atom,. ez..
- . Pc11. NHd+); excessiue (i.e..
more than eight including nonhonded electrons on centrai
atom, e.g., XeF2, BrF4-); deficient (i.e., less than eight elec-
trons on central atom, e.g., BFB,SnC12);and octet (i.e., eight
electrons including nonbonding electrons on central atom,
e.g., NH2-, SOF2). The difficulties of these skills were found
to be, in the ahove sequence, hard, average-hard, easy-aver-
age, average-hard, hard, easy-average.
If students were to follow the rules suggested in this arti-
cle. these oroblems would simnlv not arise. as the rules
faithfully executed must resu~t'ida valid ~e'wisstructure.
Once a valid structure has been obtained from these "book-
keeping" rules, the instructor is in a position to discuss the
implications of an odd number of electrons, of an excess or
deficiency of electrons, of multiple honds, etc., on the geome-
trv, properties, and reactivity of the species. An overempha-
si; on tl;e octet rule by tearhkrs and the lack of a set of iules
nor requiring rhemiral knowledge other than numbers of
valence electrons on atoms aresurely the root causes of
student difficulties.
Oxidailon Numbers
give a simnle set of rules
for writing Lewis structures, they almost all present rules
reauiring minimal knowledee of chemical facts or orinci~les
for determining the oxidation numbers of elements in a
molecule or an ion, e.g., ref 7: free element, 0; monoatomic
ion, charge of ion; oxygen, -2 except in peroxides (-1) and
OF2 (+2); hydrogen +1 except in ionic hydrides (-1); the
sum of the oxidation numhers equals the overall charge on
the species. Students often meet these rules before the con-
cept bf elertronegativity, which is the rationale for them, is
encountered, and it is not seen as a difficult topic.
Once the skill of writing Lewis structures has been mas-
tered, and the concept of electronegativity introduced, the
student can derive the oxidation numher of each atom in a
Volume 68 Number 6 June 1991 457
 undergoing bonding changes and the oxidation state of the
bridging sulfurs is zero from structure 9.

Figure 2. Examples of deriving oxidation number from Lewis structures
molecule or ion by a slight variation of our above method for
formal charee: count the number of electrons on each atom
by p e t e n d k g the bonding elections belong to the more
electronegative atom, and compare with the number of ua-
lence electrons of the neutral atom. Examples of this are
given in Figure 2.
This general rule for determining oxidation numbers
should supersede the introductory rules as soon as Lewis
structures have been mastered and electronegativity intro-
duced as it gives much more meaningful results. Where two
atoms of the same element are in different environments in a
species they may have different oxidation numbers, while
the elementary rules give an average. In thiosulfate, S20a2-,
the elementary rules give sulfur an oxidation number of +2.
The general rule would give +4 and 0 for the Lewis structure
7 and +5 and -1 for structure 8. The latter is probably the
better representation for regarding its oxidation to tetra-
thionate by iodine, as it is the peripheral sulfur atom that is
Conclusions
In many areas and stages of education one progresses by
mimicking by ear, or learning a set of rules by rote, or by
following written instructions. The rationale or understand-
ing comes later, if a t all. This approach has generally been
used successfully to teach the determination of oxidation
numbers in soite of the limitations of the elementary rules
but not so often in teaching the skill of writing Lewis struc-
tures, even though Lewis structures form a basic part of a
chemist's writtenlanguage and are used in developing more
sophisticated models (e.g., in representing reaction mecha-
nisms). This paper presents a set of rules for writing Lewis
structures requiring only the ability to add and subtract,
count, and know the number of valence electrons of neutral
atoms. The early introduction of these rules and practice in
using them would remove many problems students encoun-
ter in studying chemistry.
I t is unrealistic to exoect students a t a n early stage to
deduce the arrangement of atoms in many species just from
condensed formulae as implied in refs 1 and 2. This requires
considerable knowledge a i d experience, and therefore the
ability to know which is the "central atom" should not be
considered as a necessary skill to he acquired when Lewis
structures are first introduced.
Literature Cited
I. Pnrdo.Q.3 Chrm.Edue. 1989.66.456-458.
2. B ~ Y , JA,:. Milbury-Steen..l.N.: Burrnei3ter.J. L. J Cham. Edur. 1990.67.491-493.
3. Snsdden, R. B. Edvr. Chem. 1987.24.81-83.
I. Gillespie.R.J.: Hurnphreya. D,A,: Bsird. N. C.: Robinson. E. A. Chemistry: Allyn and
,,,,"*"".
Bacon: Boston, 18PL'-qoE
r, J. E. A Chemistry G ~ i d ~ b a o3rd
b . ed.: Heinomsnn: Auekland,

Eleventh International Conference on Chemical Education

The Eleventh International Conference an Chemical Education (ICCE),sponsored by The Royal Society of Chemistry
and the International Union of Pure and Applied Chemistry, will he held August 25-30,1991, inYark, U.K. The theme
of the Conference,which is held biannually, is "Bringing Chemistry to Life", and a series of special topics lectures will
be presented that are particularly relevant to that idea. Included are: Chemistry in the Atmosphere, Chemistry and
Crop Protection, Liquid Crystal, Problems in the Cell, and New Petroleum Chemistry. Teaching issues related to the
central theme that will he explored through symposia and workshops include: making chemistry accessible to all
students, new curricula atprimary, secondary, and past-secondary levels, new teaching strategies at all levels, teaching
and learning at a distance, new frontiers of chemistry and their impact on teaching, and research in chemical education.
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including local scenic areas. Registration far a participant is £165 and for each accompanying person, £75. Room and
board for the Conference can also be arranged forE150per person. Accomodations are in a student dormitory, and meals
will he provided from the buffet reception on Sunday, August 25, through lunch on Friday, August 30.

458 Journal of Chemical Education