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Chemical Bonding 10
Chapter Overview

Understanding how atoms bond gives us the power of predicting chemical behavior.
Drawing Lewis structures and predicting the resulting molecular shapes is discussed. The
chemical interactions based on shape, including electronegativity and polarity, are also
explained.

Lecture Outline

10.1 Bonding Models and AIDS Drugs

A. Bonding theories attempt to explain actual structures
B. Some theories work for some molecules but not for others
10.2 Representing Valence Electrons with Dots
Learning Objective: Write Lewis structures for elements.
A. Valence electrons are outermost shell electrons
B. Lewis structure of an atom is simply chemical symbol + valence electrons around it
C. Most atoms “want” eight electrons around them (octet rule)
D. Exception: duet rule for hydrogen and helium
E. A covalent bond is a shared pair of electrons to achieve an octet around each atom
10.3 Lewis Structures for Ionic Compounds: Electrons Transferred
Learning Objective: Write Lewis structures for ionic compounds.
Learning Objective: Use the Lewis model to predict the chemical formula of an ionic
compound.
A. Metal atom effectively gives valence electrons to the nonmetal
B. Metal is positively charged, nonmetal is negatively charged
C. Attraction of opposite charges constitutes the ionic bond
10.4 Covalent Lewis Structures: Electrons Shared
Learning Objective: Write Lewis structures for covalent compounds.
A. Two bonded nonmetals share electrons such that both get an octet (or duet)
B. Both species get “credit” for all electrons in bond
C. Two species can share two, four, or six electrons
1. Two electrons shared is a single bond
2. Four electrons shared is a double bond
3. Six electrons shared is a triple bond
10.5 Writing Lewis Structures for Covalent Compounds
Learning Objective: Write Lewis structures for covalent compounds.
A. Write the correct skeletal structure for the molecule
B. Calculate the total number of valence electrons
C. Distribute electrons among atoms giving each an octet (or duet)

Copyright © 2015 Pearson Education, Inc. Page 41

 D. If any atoms then lack an octet, form double or triple bonds as necessary
E. Exceptions to the octet rule
1. Duet rule for hydrogen
2. Odd number of electrons
3. Boron usually has only six electrons about it
4. Some elements in the third row and beyond may have more than eight electrons
around them
10.6 Resonance: Equivalent Lewis Structures for the Same Molecule
Learning Objective: Write resonance structures.
A. More than one possible Lewis structure
B. True structure is average of all Lewis structures
10.7 Predicting the Shapes of Molecules
Learning Objective: Predict the shapes of molecules.
A. VSEPR theory
1. Electron groups repel each other
2. Electron geometry
a. Linear
b. Trigonal planar
c. Tetrahedral
B. Predicting structures
1. Draw the Lewis structure
2. Count the number of electron groups
3. Determine the number of bonding groups and lone pair groups
4. Determine electron geometry and molecular geometry
10.8 Electronegativity and Polarity: Why Oil and Water Don’t Mix
Learning Objective: Determine whether a molecule is polar.
A. Electronegativity
B. Bond dipoles
C. Dipole moment
D. Polar and nonpolar bonds
E. Polar and nonpolar molecules

Chemical Principle Teaching Ideas

Lewis Structure
All covalent bonds involve the sharing of electrons. By understanding how the atoms
bond to each other, the students can begin to understand why species react the way they do.

Molecular Shapes
The most effective way for students to remember the various molecular shapes is to
memorize one example of each. For example, remember that NH 3 is trigonal pyramidal and has
three bonds and one lone pair. H 2 O has two lone pairs and two bonds, and the geometry is bent.

Electronegativity
Some atoms hold on to electrons tighter than others. In some interactions, the bonding is
therefore uneven. Atoms are involved in a sort of tug-of-war with the electrons. A purely

Copyright © 2015 Pearson Education, Inc. Page 42

covalent bond involves two equal strength opponents resulting in equal sharing. An ionic bond
involves one species that is much stronger than the other, resulting in complete electron transfer
with no sharing.

Skill Builder Solutions

10.1. Magnesium has just 2 valence electrons, so the Lewis structure is •Mg•

10.2. NaBr is an ionic compound, so Na donates the 1 valence shell electron it has to bromine,
which then has an octet in its valence shell. Sodium has a +1 charge and Br has a –1

charge. The Lewis structure is thus Na+ [: Br :]-


10.3. Since Mg has a +2 charge and N has a –3 charge, the molecular formula is Mg 3 N 2 . The
 
Lewis structure is Mg+2[: N :]-3 Mg+2[: N :]-3 Mg+2
 

10.4. Carbon monoxide has a total of 4 + 6 = 10 valence electrons. The skeletal structure is
C-O, and then we add electrons around the outer atoms, giving them octets. We can start

with : C- O :, but carbon does not have an octet, so we must form a triple bond with the


oxygen atom, giving :CO: or :C:::O:

10.5. There are a total of 12 valence electron in this species. Following the symmetry
guidelines, and placing 2 electrons in for each bond, we get

Now add the remaining electrons around the outer oxygen atom

To give the carbon atom an octet, we must move a lone pair from the oxygen

Which gives our final Lewis structure

10.6. The species has 7 electrons coming from the Cl and 6 coming from the O atom. This
makes a total of 13, but one more comes from the –1 charge of the ion, for a total of 14.
The two species share one pair of electrons, to give each an octet. The Lewis structure is
 
[: Cl : O :]-
 

Copyright © 2015 Pearson Education, Inc. Page 43

   
10.7. The base Lewis structure is [: O - N - O :]-. The nitrogen has only 6 electrons around it,
 

so it wishes to make a multiple bond with one of the oxygen atoms. It does not matter
  
from which oxygen it comes, so there are two possible resonance structures: [ O = N - O :]-
 
  
 [: O - N = O ]-
 

10.8. The central nitrogen has three groups of electrons around it, two of which are bonds and
one is a lone pair. The electron geometry is then trigonal planar, and the molecular
structure is bent.

10.9. The central sulfur atom has four groups of electrons around it: one a lone pair and
three bonds. This gives tetrahedral electron structure and trigonal pyramidal molecular
geometry.

10.10. a. Because two iodine atoms have the exact same electronegativity, neither is stronger
than the other. Therefore, the bond is pure covalent.
b. Cesium is a group IA metal, and bromine is a group VIIA nonmetal. When they
bond, there is a transfer of the electrons, giving an ionic bond.
c. Phosphorus and oxygen are both nonmetals and are significantly different in
electronegativity. When they bond, the electrons are shared, but oxygen has a
larger pull, so there is a small dipole moment. The bond is polar covalent.

10.11. CH 4 has a tetrahedral electron geometry and a tetrahedral molecular geometry. Since all
of the bonds are of the same slight polarity in terms of electronegativity difference and
the bonding is symmetric, the bond dipoles cancel each other out. Thus, the overall
molecule is nonpolar.

Suggested Demonstrations

Blow up four equally sized balloons and tie the knots together. The resulting structure is
tetrahedral in geometry, and you can explain how the balloons try to get as far apart as possible.
Then pop one of the balloons to show how three orbitals (balloons) orient themselves. Then pop
another balloon and explain the resulting structure change.

Have a few students (of various sizes) come to the front of the room and have them make various
molecular geometries by holding arms in various orientations. This is an effective method for
showing bond dipoles, dipole moments, and polarity.

Guided Inquiry Ideas

Below are a few example questions that students answer in the guided inquiry activities provided
in the Guided Activity Workbook.

Which atom do you think is central in carbon dioxide? Why?

Copyright © 2015 Pearson Education, Inc. Page 44

Carbon dioxide has two groups of electrons surrounding the carbon atom. Why is the OCO bond
angle in CO 2 180°?

The four groups of electrons in methane get as far from each other as possible. Is the angle
between them 90°? If not, what is it?

Can a molecule with no polar bonds be polar?

Is a linear molecule the only one in which all the polar bonds cancel? What other geometric
arrangement of polar bonds also leads to all the polar bonds canceling?

Copyright © 2015 Pearson Education, Inc. Page 45

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 PLATE CCCLXXX.

ACHYRANTHES PORRIGENS.
Divaricating Achyranthes.
CLASS V. ORDER I.

P E N TA N D R I A M O N O G Y N I A . F i v e C h i v e s . O n e P o i n t a l .
ESSENTIAL GENERIC CHARACTER.
Flores incompleti, inferi. Calyx 5-phyllus. Corolla 0. Stigma 2-fidum.
Semina solitaria.
Flowers incomplete, beneath. Empalement 5-leaved. Corolla none.
Summit 2-cleft. Seeds solitary.
SPECIFIC CHARACTER, &C.
Achyranthes, foliis oppositis, lanceolatis, spicis ovatis, acutis. Jacq.
Hort. Schœnb. 3. 349. t. 350.
Achyranthes, with leaves opposite, spear-shaped, and egg-shaped
sharp-pointed spikes.
Descriptio. Suffrutex ramulis distantibus, filiformibus, canescentibus.
Folia opposita, elliptico-ovata, breviter petiolata, obsolete venosa, supra
pallide viridia lente pubescentia; subtus pallidiora magisque pubescentia.
Flores dichotome-paniculati, divaricati, capitulis ovalibus, persistentibus,
ante et post exsiccationem læte purpureis pulchellisque, ut in Gomphrenâ
perenni.
REFERENCE TO THE PLATE.
1. A flower complete.
2.The empalement magnified.
3.The blossom magnified.
4.The same cut open.
5. The seed-bud and pointal
Achyranthes porrigens was introduced into this country from Paris, in the
year 1802, by Mr. Woodford of Vauxhall; but its native country we have not
ascertained. Our figure was taken from a fine plant in the collection of J.
Vere, esq. at Kensington Gore; where it is considered and treated as a hot-
house plant of the more hardy kind; and rises to the height of 2 or 3 feet.
Thrives well in rich earth, and flowers freely in spring, making an elegant
but not showy appearance. Its flowers resemble those of Gomphrena
perennis, and like them preserve their colours after death, if gathered before
they are fully blown; and are capable of becoming both a novel and a
graceful addition to our dried bouquets. Is propagated by cuttings, and
promises fair to ripen seeds; but is at present extremely rare.
 PLATE CCCLXXXI.

S A R R A C E N I A F L AVA .
Yellow Side-saddle Flower.
CLASS XIII. ORDER I.

P O L YA N D R I A M O N O G Y N I A . M a n y C h i v e s . O n e P o i n t a l .
ESSENTIAL GENERIC CHARACTER.
Capsula 5-locularis. Stigma clypeatum. Calyx exterior 3-phyllus,
superior 5-phyllus.
Capsule 5-celled. Stigma shield-shaped. Calyx outer 3-leaved, upper 5-
leaved.
SPECIFIC CHARACTER, &C.
Sarracenia, foliis erectis tubulatis, valva collo contracta, apice plana
erecta.
Sarracenia, with erect leaves, the valve contracted in the neck, with its
point flat and erect.
Sarracenia flava, Walt. Fl. Carol. 153.—Aiton Hort. Kew. 2. 225.—
Willd. Sp. Pl. tom. 2. 1150.
REFERENCE TO THE PLATE.
1. A back view of the flower.
2. A flower deprived of its superior calyx leaves, showing the situation and structure of the
stamina and style.
Few of the productions of Flora exhibit such extraordinary appearances
as those of the small but interesting genus Sarracenia: whether we
contemplate their tubulose, water-holding, lidded leaves; or the strange
conformation of their flowers; but more especially their enormous shield-
shaped stigmata.
Walter enumerates four species of Sarracenia in his Flora Caroliniana, all
perennial-rooted; and all at this time existing in the London gardens; but
they are rare.
 The Side-saddle Flowers are rather difficult of cultivation, and succeed
best when treated as green-house bog plants; and when plentifully supplied
with water. They are propagated by dividing their roots in spring. The
specimen from which our figure was taken, was obligingly sent us by the
honourable Mr. Irby of Farnham Royal, Bucks.
 PLATE CCCLXXXII.

L I PA R I A V I L L O S A .
Concave-leaved Liparia.
CLASS XVII. ORDER III.

D I A D E L P H I A D E C A N D R I A . Tw o B r o t h e r h o o d s . Te n
Chives.
ESSENTIAL GENERIC CHARACTER.
Calycis lacinia infima elongata. Alæ inferius bilobæ.
The lower segment of the empalement elongated. The wings two-lobed
on the lower margin.
SPECIFIC CHARACTER, &C.
Liparia, floribus fasciculatis, foliis subrotundis concavis, extus
tomentosis, intus villosis nudisque.
Liparia, with fasciculated flowers, leaves roundish concave, downy
outwardly, and villose or naked within.
Liparia villosa α. Willd. Sp. Pl. 3. 1117. excluso synonymo Thunbergii;
quod ad varietatem β. potius pertinet.
Liparia vestita, floribus capitatis, foliis ovatis concavis subtus lanatis.
Thunb. Prod. 124. et etiam Willd. Sp. Pl. 3. 1115.
Genista africana tomentosa, folio cochleariformi, flore luteo. Seba Thes.
1. p. 38. tab. 24. f. 1.
REFERENCE TO THE PLATE.
1. The empalement.
2.The banner.
3.One of the wings.
4.The keel.
5.The chives and pointal.
6. The seed-bud
The Liparia villosa is a native of the Cape of Good Hope, and rises with a
shrubby, but not much branched stem, to the height of two or three feet. The
silvery wool which clothes the younger branches and leaves of the plant,
gives it a very handsome appearance; yet by age it sometimes acquires a
somewhat rusty tint. The leaves are nearly round, and assume, particularly
when dried, a deep concave form, and very much resemble in shape, small
bivalve shells; a circumstance noticed long since by the great naturalist Seba,
as will appear on consulting the synonyms above given. The variety β. of
Willdenow has much narrower, and not concave leaves; and is a very distinct
species.
The concave-leaved Liparia is propagated, but not readily, by cuttings;
prefers the treatment of a green-house plant, a light, but good soil; and, like
most woolly plants, is very liable to be destroyed by damps. Our figure was
taken in May last at George Hibbert’s, esq.
 PLATE CCCLXXXIII.

P I T T O S P O R U M U N D U L AT U M .
Waved-leaved Pittosporum.
CLASS V. ORDER I.

P E N TA N D R I A M O N O G Y N I A . F i v e C h i v e s . O n e P o i n t a l .
ESSENTIAL GENERIC CHARACTER.
Capsula 2-5-locularis, 5-valvis. Semina tecta pulpa. Petala conniventia in
tubum.
Capsule 2-5-celled, 5-valved. Seeds covered with pulp. Petals
converging into a tube.
SPECIFIC CHARACTER, &C.

Pittosporum, foliis lanceolatis undulatis acutis.

Pittosporum, with lance-shaped, waved sharp-pointed leaves.
Descriptio. Frutex erectus, ramosus. Ramuli fusci, cicatricibus foliorum
asperi. Folia breviter petiolata, lanceolata, vel elliptico-lanceolata, acuta,
undulata, rigida, lucida, viridia, et reticulatim venosa; subtus pallidiora.
Flores terminales, racemosi, albicantes, pedunculis inæqualibus,
rufescentibus, obsolete bracteatis. Calyx 5-fidus, deciduus, laciniis acutis,
recurvis. Corolla, petala 5, lineari-lanceolata, obtusa, revoluta, inferne in
tubum conniventia. Stamina, filamenta 5, receptaculo inserta, stricta,
subulata, subcompressa, altitudine styli; antheræ erectæ, luteæ. Stylus
albidus, petalis brevior. Stigma obtusum.
REFERENCE TO THE PLATE.
1. The empalement.
2.One of the petals.
3.The chives and pointal, with one tip magnified.
4. The pointal and seed-bud magnified
The Pittosporum undulatum is a new plant, introduced into this country in
the year 1793 from New Holland, where it is a native. It rises with a shrubby
stem, which is branched above, to the height of several feet. Its branches are
adorned with a fine undulated foliage that is rigid to the touch; and are
terminated, in the month of May, with bunches of whitish flowers.
Is as yet a very rare species, and is raised from imported seeds; and
likewise by cuttings. Requires, and thrives well with, the common treatment
of a green-house or conservatory plant; and deserves a place in every
extensive collection. Our drawing was made from a specimen in the Nursery
of Messrs. Colvil, in the King’s Road.
 PLATE CCCLXXXIV.

X E R A N T H E M U M VA R I E G AT U M .
Variegated Eternal Flower.
CLASS XIX. ORDER II.

S Y N G E N E S I A P O LY G A M I A S U P E R F L U A . Ti p s u n i t e d .
Superfluous Pointals.
ESSENTIAL GENERIC CHARACTER.
Receptaculum paleaceum, aut nudum. Pappus setaceus. Calyx
imbricatus, radiatus; radio colorato.
Receptacle chaffy, or naked. Feather bristly. Empalement tiled, rayed:
the ray coloured.
SPECIFIC CHARACTER, &C.
Xeranthemum, floribus solitariis nutantibus, squamis calycinis obtusis
maculatis.
Xeranthemum, with solitary nodding flowers, and the scales of the
empalement obtuse and spotted.
Xeranthemum variegatum. Syst. Veg. 614.—Syst. Veg. Litchf. ed. 2. p.
614.—Reich. Syst. Pl. pars 3. 766.
Xeranthemum africanum Gnaphalii foliis tomentosis, foliis et
squamorum summitatibus ferrugineis. Raii Suppl. 181.
REFERENCE TO THE PLATE.
1. An hermaphrodite floret magnified.
2.The chives, pointal, and seed-bud magnified.
3.One of the scales of the empalement.
4. The receptacle
The Xeranthemum variegatum is a small shrub, and seldom attains the
height of two feet. It is a native of the Cape of Good Hope, and was lately
introduced from that country to the collection of George Hibbert, esq. where
our drawing was taken in the month of May. It requires the same treatment
as the other species of the genus, and is propagated in the same manner. The
leaves are linear-lanced, embrace the stem alternately, and when old are
often reflexed in an imbricated manner: they are clothed, as well as the
stems, with wool; and resemble fine woollen cloth to the touch, and often
have their edges and points of a purplish rusty colour. The bracteated
peduncles are from one to three in number, at the end of each branch. The
young flowers are more highly coloured than the old ones, which sometimes
assume a nodding attitude: when aged they bleach almost white, except the
points of the calycine scales, which always retain a purplish blotch.
 PLATE CCCLXXXV.

C A M PA N U L A L A C I N I ATA .
Ragwort-leaved Bell Flower.
CLASS V. ORDER I.

P E N TA N D R I A M O N O G Y N I A . F i v e C h i v e s . O n e P o i n t a l .
ESSENTIAL GENERIC CHARACTER.
Corolla campanulata, fundo clauso valvis staminiferis. Stigma 3-fidum.
Capsula infera, poris lateralibus dehiscens.
Corolla bell-shaped with the mouth closed by staminiferous valves.
Summit 3-cleft. Capsule beneath, gaping with lateral pores.
SPECIFIC CHARACTER, &C.
Campanula, capsulis obtectis pedunculatis, foliis serratis; radicalibus
lyratis; caulinis lanceolatis.
Bell Flower, with pedunculated covered capsules, and serrated leaves;
the root ones lyrated; the stem ones spear-shaped.
Campanula laciniata. Willd. Sp. Pl. 1. 911.
Campanula Græca, saxatilis, Jacobeæ foliis. Tourn. Voyage 1. 201. cum
icone.—Coroll. Inst. Rei Herb. 3.
Descriptio. Herba undique villosa. Radix biennis. Folia radicalia lyrato-
pinnatifida, pinnulis incisis; caulina alterna, sublanceolata, inciso-serrata.
Pedunculi bracteis subovatis dentatis instructi. Flores numerosi cærulei.
REFERENCE TO THE PLATE.
1. The empalement.
2.The blossom laid open.
3.The seed-bud, chives and pointal.
4.A chive magnified.
5. The seed-bud and pointal, the summit magnified
The Campanula laciniata, although introduced into the British gardens so
long since as the year 1790, is still a very scarce species: this is not owing to
a want of beauty, but to its having a biennial root, and not perfecting its
seeds well, except in favourable situations. It was originally discovered by
the celebrated French traveller and botanist Tournefort, about a century
since, on a remarkable rock in the Island of Sikino in Greece; where he
appears to have been highly delighted with its beauty and appearance, and
says it is “the fairest Campanula in all Greece[B].” However applicable this
encomium may have been in those days, it ceases to be so now; for, without
detracting from the fairness and beauty of the present plant, we have in
cultivation another Grecian Campanula, still more fair and beautiful, and
much more rare, which we hope soon to have the pleasure of presenting to
our subscribers.
The Ragwort-leaved Campanula is usually treated as an alpine plant, and
wintered in a frame: it is increased by seeds, and is impatient of superfluous
moisture.
[B] Tournefort’s Voyage, vol. i. page 201.
 PLATE CCCLXXXVI.

ANTHERICUM PUGIONIFORME.
Dagger-leaved Anthericum.
CLASS VI. ORDER I.

HEXANDRIA MONOGYNIA. Six Chives. One Pointal.

ESSENTIAL GENERIC CHARACTER.
Calyx patens aut connivens. Stamina filamentis filiformibus hirsutis.
Stigma 1. Semina angulata. Juss. Gen. Pl. 52.
Empalement expanding or converging. Chives thread-shaped hairy.
Summit 1. Seeds angulated.
SPECIFIC CHARACTER, &C.
Anthericum, foliis carnosis linearibus acuminatis canaliculatis, scapo
foliis duplo longiore.
Anthericum, with fleshy linear acuminated channelled leaves, with a
stalk twice their length.
Anthericum pugioniforme. Willd. Sp. Pl. 2. 144.
Anthericum filamentis barbatis acaule, radice subrotunda perenni, foliis
crasso-subulatis antice sulcatis apice teretibus pulposis erectis. Jacq. Ic. rar.
2. t. 405.
Petala sex, oblonga, obtusa, plana, patentissima, lutea, cum fascia
longitudinali media utrinque viridi. Filamenta subulata patula, petalis
breviora, flavescentia, circa medium omnia ex viridi-flavo dense barbata.
Antheræ oblongæ, flavæ. Germen ovatum, superum. Stylus filiformis,
erectus, longitudine staminum. Stigma obtusum. Jacq. Collect. Supp. 83.
REFERENCE TO THE PLATE.
1. The seed-bud, chives and pointal.
2.A chive magnified.
3. The seed-bud and pointal
A native of the Cape of Good Hope, from whence it was sent some time
since to the collection of G. Hibbert, esq. Clapham Common; where our