JURONG JUNIOR COLLEGE

H2 CHEMISTRY
CHEMICAL BONDING (2008 JCI)

Gontent
. lonic (electrovalent) bonding
o Gslebnt bonding and co-ordinate (dative covalent) bonding
. The shapes of simple molecules
. Bond energies, bond lengths and bond polarities
. k*smolecular forces, including hydrogen bonding
. He{aHic bonding
. Bonding and physical ProPerties
r The solid state

Assessment Obiectives
Students should be able to:

I (a) describe ionic (electrovalent) bonding, as in sodium chloride and magnesium oxide, including the use of
'dot-and-cross' diagrams
(b) describe, including the use of 'dot-and-cross' diagrams'
covale-nt bonding, as in hydrogen; oxygen; nitrogen; chlorine; hydrogen chloride; carbon
zO
dioxide; methane; ethene
,/(ii) co-ordinate (dative covalent) bonding, as in formation of the ammonium ion and in the Al.Clu
molecule.
lc) explain the shapes of, and bond angles in, molecules such as BF. (trigonal planar); CO, (linear); CHo
(tetrahedral); NH. (trigonal pyramidal); HrO (non-linear); SF. (octahedral) by using the Valence Shell
Electron Pair RePulsion theory
describe covalent bonding in terms of orbital overlap' giving o and n bonds
' (d)
7
(ei preOict the shapes of, and bond angles in, molecules analogous to those specified in (c)
OescriOe hydrogen bonding, using immonia and water as examples of molecules containing -NH and
-OH
7 if;'
9roups
,19; 6xptiin the terms bond energy, bond length and bond polarity and use them to compare the reactivities of
covalent bonds
,, (h) describe intermolecular forces (van der Waals' forces), based on permanent and induced dipoles, as in
CHC/3(I); Brr(l) and the liquid noble gases
,(i\ describe metallic bonding in terms of a lattice of positive ions surrounded by mobile electrons
' iJi JescriO", interpret and/oi predict the effect of different types of bonding (ionic bonding; covalent bonding;
!. hydrogen bonding; other intermolecular interactions; metallic bonding) on the physical properties of

I (k)
',,iti
substances
deduce the type of bonding present from given information
show understanding of chimical reaction-s in terms of energy transfers associated with the breaking and
making of chemical bonds
(m) describe, in simple terms, the lattice structure of a crystalline solid which is:
0 ionic, as in sodium chloride, magnesium oxide
(iD simple molecular, as in iodine
(iiDgiant molecular, as in graphite; diamond
(iv)hydrogen-bonded, as in ice
iui metallic, as in copper [the concept of the 'unit cell' is not required]
(n) ouline the importance of hydrogen bonding'to the physical properties of substances, including ice and
water
(o) suggest from quoted physical data the type of structure and bonding present in a substance
ioi reCoonise that materials are a finite resource and the_importance of recycling processes
iii O"r"iiU" spt hybridisation, as in ethane molecule, spt hybridisation, as in ethene and benzene molecules,
molecule.
and sp hyliridiiation, as in ethyne [from 10.1 Organic Chemistry] , ,
(r) explain the shapes ol and bond angles in, molecules analogous to those specified in (e)
[from 10.1 Organic Chemistry]

References:
1. R'dmsden; "A Level Chemistry", 4th edition.
2" Hill and Holman; "Chemistry in Context", 4th edition.

JJC 2008
Page 1 of 42
1. INTRODUCTION

x As we examine the world around us, we find it to be composed mainly of elements, compounds and
mixtures. The manner in which the atoms are bound together has a profound effect on the chemical and
physical properties of these substances. For example, graphite is soft and slippery while diamond is the
hardest substance known. Such differences in physical properties are best explained by the bonding
within these substances.

x A e:frcmfesfS@d is the daceda6re"@ieg,- typically between a ffl*I}

Jhere are 4 main types of chemical bond.

Positive charge Negative charge Type of chemical bond

!ELn6 *ils ffi**

Electrostatic theno$lil{e rmbi of the bonding electrons
attraction and
the 2 atoms shared between them
between

nnffiilss naHdnns rlH&Sond

Electrostatic attraction between r* due to the setting ddir*g %es t
x Because chemical bond refers to the electrostatic attraction between point charges of opposite charge,
theWrld can be predicted by Coulomb's Law.

x
\\^c\rt
GMb'o.Law: describes the mrunihsde"r#eedd@db*oreWxeem*** ct€r,ges
Xdow\ nA?J tui..ei,w;tik- f c.lnotrqeJ

Me*ry where Q* & q- are charges of positive & negative points;

d is distance between the two point charges

Note that Coulomb's Law is covered under Physics buf NOT in the Chemistry syllabus"

ln this topic, we shall study the different types of chemical bond and understand how they affect the
physical properties of materials ll

JJC 2008
Page 2 of 42

----l
 Figure 1.1 An Overview of Structure and Bonding

IONIC BONDING COVALENT BONDING METALLIC BONDING

I (INCLUDTNG DATIVE COVALENT BOND) I

I
I I
I
I
I

Giant lonic Sr'mple Mol ec u Ia r/C ova Ie nt Giant M ol ec u Ia r/C ovalent Giant Metallic
Structure Structure Structure -I-"i r' 1
Structure
t'vi' d .,=1-- F,-JE-; .,f"' . ti''-"j i ( :; t, :1"-,---
i i
contains simple
i
l'-
\
t-.--*... ,-r,,.., i
Limited examples: graPhite, i"' I\r-:i\f1 i

molecules which
\---'
l'!r'i\'ri
are held by diamond, silicon, SiOz

INTERMOLECULAR FORCES

Hydrogen Bonding van derWaals'forces

I
between polar Pe rmanent Dipole-Pe rm an ent Di pole In du ced Dipole-l nduced Di Pole
molecules thal Attracti on (P D -P D aft racti on ) Aftraction (ID-ID aftraction)
contain H directly
I
bonded to I
I
F,OorN I

between polar molecules between non-polar molecules/atoms

I
I
I I
HF, NH3, H2O, I I

HC/, CHC/3, HCHO Hz, Clz, Brr, COr, CHa

cH3cH20H,
cH3cocH3, CC/., He, Ne, Ar...etc
cH3cooH,
CHrCONHr...etc CH.OCH....etc

Sorne Useful Concepts

. 1" Atomic radius/size
Across a period, atomic radius decreases gradually because nuclear charge increases as the number
-: of protons in the nucleus increases while the valence electrons occupy the same outermost shell.
Thus, electrons are drawn closer to the nucleus.

Down a group, atomic radius increases because the number of quantum shells that contain electrons
increases.
**This concept is useful in determining the strength of chemical bond.

':i t ' ' -''f\;r r"

tr-' ''
2" Electronegativity -
Electronegativity refers to the ability of an atom to attract fdditional electronstto itself.
The higher the electronegativity value, the more electronegative the atom is.
Table 1.1 Electronegativity values for main group elements (based on Pau
H 2.1 He
Li 1.0 Be 'l.5 B 2.0 c 2.5 N 3.0 o 3.5 F 4.0 Ne-
Na 0.9 Mq 1.2 A/ 1.5 si 1.8 P 2.1 s 2.5 c, 3.0 Ar
K 0.8 Ca 1.0 Ga 1.6 Ge 1.8 As 2.0 Se 2.4 Br 2.8 Kr
Rb 0.8 Sr 1.0 ln 1.7 Sn 1.8 sb 1.9 fe 2.1 |
2.5 Xe

Across a period, electronegativity increases.

Down a group, electronegativity decreases.

JJC 2008 Page3ol42

 -.:.> Therefore, metals have low electronegativity and they tend to form
cations.
Non-metals have high electronegativity and they tend to form anions.
lmplications:
Efements in a compound with large electronegativity difference
tend to form ionic bonds.
Elements in a compound with small electronegativity difference
tend to form covalent bonds.
..r. I :

The concept of electronegativity and difference in electronegativity values

is useful in predicting the type
of bonding and structure present in an elemenVcompound.

3. Metals and non-metals.

H
Li Be He
B c N o F Ne
Na Mo Sc Ti Cr Mn Fe Co Ni Cu Zn AI Si P S cl Ar
K Ca Zr Nb Mo Tc Ru ni
Rh Pd Aq Ga Ge As Se Br Kr
Rb Sr La Hf Ta W Re Os' lr Pt Au Hq In Sn sb Te I Xe
Cs Ba Ac Rf Db So Bh Hs Mt TI Pb Bi Po At Rn

4. Noble Gas Configurations

All noble gases are. chemically stable or inert. They are extremely unreactive.
Their stabilities are
related to their electronic co_nfigurations. The number of electrons
in the outer shell of a nbble gas is
8 (ns2npo) except for He 1ts2;. inus, stability is gained when the atom
is in the octet state. This is known
as the octet rule.

ln 1916, w' Kossel and G.N. Lewis explained the formation of chemical
bond. Atoms can achieve the
stable octet structure by
(a) transferring electrons from one atom to another
i.e. forming ionic bonding
(b) sharing electrons between atoms
i.e. forming covalent bonding

5' Heat is released (evolved) during bond formation (AH is negative). +.ri -r.\'i
Heat is absorbed during bond breaking (AH is positive).-; .,,. 1.,'^,,1r',,, ,

Exercise 1: with reference to Figure 1.1, predict the bonding and structure of the following substances.

Substances Bonding Structure

Rubidium i 'l * ''t -l ,-,_ t,\...\ .+- ; _\/, *,.
J .- )

Silicon,. \* ia\:

Bromine i:, \

Mgo il' n: r'r l ' r

Hzo 1,
r.i-). );-\.iir. .,2 , _,r,\i.-r,' ,.,,'1r i . '., .-'f
l:! : )'1.. ii]' r-v.;l;'i t, ,,,
si02 rr .\
\,..
t,/\"f l
J ' r''-

JJC 2008 Page 4 of 42

 2. METALLIC BONDING
2"1 Metallic Bondinq in Metals

A metal consists of a lattiee of metal cations surrounded by mobile electrons which are the valence
electrons of the metal atoms (see Figure 2.'t).

Figure 2.1 Model of a metal: Lattice of positive ions surrounded by mobile electrons

o".o"o"o.o Metal #ms bse their

o"o"o"o" valence electrons to

achieve the stable noble

o"o"o"o'o gas configuration.

a As shown in Figure 2.1, metallic bond exists extensively throughout the whole structure.
Thus metals are said to have giant metallic structure.

2.2 Strenqth:of Metallic B

Recafl Coulomb's Law: F qql*q_^-
Two main factors affecting the strength of metallic bond: d"
1. Number of valence electrons
1\Ailr'tr I \)'''
As the number of valence electrons increases, the charg.e of the positive metal ions
and the number of mobite electrons ' 'n i-ri'-i-*ir'!:'r . Thus, the metallic bond becoms5 :''-i"'! i "'i'\i- -, .

e.g. strength of metallic bond of Na < Mg < A/

't J]:,:
ti,;i.j' =;Ji|
2. Charge density of the metal ion

charse on the ion

T Charge density of an ion =
size of ion

rJ' .t"r"l;
- I
For metal ions with the same charge, 16." i'rttl'\ the size of the ions, the ,n"
charge density of the ions, ths ifl^Jl,/r l:/.,will be the electrostatic attraction for the mobile electrons.
e.g" strength of metallic bond of Na > K > Rb

Therefore, metallic bond strength increases with increasing number of valence electrons and with
increasing charge - density of the metal ion (decreasing size and increasing charge).
Hence, metallic bond strength increases across the period and decreases down the group.

JJC 2008 Page 5 of42

:-::-:-=.
2.3 Phvsical Properties of Metals

1. Volatility
Metals generally have melting and boiling points (or low volatility) because large
amount of energy is required to overcome the strong
electrostatic attraction between positive
metal ions and mobile electrons.
Melting and boiling points of metals increase as the
strength of metallic bond increases"
E.g- melting point of Na < Mg < At white metting point
of Na > K > Rb
Table 2.1 Melting and boiling points of some metals in oC

2" Thermal Conductivity

Metals are good heat conductors becEuse heat travels
vibrationsandcoltisionsofthe i:1 ,.r;-' ir t'
through the metal lattice as a result of the raoid

Figure 2.2 Metals conduct heat well

hot end cotd end

ffiIXT
stror€ty
;,ff:'il;X:,
tess strongly
, i, '

3. ElectricalGonductivity
good electricat conductors in the and , -' '
ltelals 1re I ' : states because there are
11
' ' ' ' that can carry charges through the metal lattice. (Etectric curentresulfs from a net
flow of charges.) Etectricat conductivity (units: o-t cm-t;
lncreases.
lncreases as number of mobite electrons

Figure 2.3 Electrical conductivity of metal

a:.:: ::

@=. Q-@ -@"' @

.'+ -n,1@"o-ieJ@-".Q
:a- =r - :a:ra : 3l
Direction of @-@_@ _@ =.@ Mobile electrons
Direction of
electron flow ,noldrE through Ulq
tanice carryir€: current flow
negalive charges

Table 2'2 Electricar conductivities of some metars |n 196 Eg-l gm-1

Li 0.108 Be 0.313
Na 0.210 Mq 0.226 At
0.377
K 0.139 Ca 0.298

JJC 2008 Page 6 of42

 4. Solubility
Metals are generally insoluble in polar solvents such as water and non-polar solvents such as
hexane, benzene.
(strictly speaking), with water to
However, some reactive metals such as K, Na, Ca can react, not dissolve
give a solution. e.g. Na(s) + Hzo(t) -> NaoH(aq) + %Hz@)

Metals may be soluble in liquid metals forming alloys'

5. Hardness
metals are
Metals are fairly hard. lts hardness depends on the strength of the metallic bond. However,
'@an
be bent or pressed into different shape) sni ct.i c;'ri p (can be pulled into wires)
;;;\J;rlJ
because the layers in the lattice can slide over each other without breaking the strong metallic
bond.
tv
g=;a; lrmetars

n
",";",;ffi ry'uct 9;qffi-
is bent.
When a force is applied, metallic bond is not broken. Thus, metals will not break when it

Exersise2: (a) Describe the structure and bonding present in aluminium"

(b) Exptainwhy the electrical conductivity of aluminium is higher than that of sodium.
r- ruott'+-)\t
qlo \^-.* +^qrr'$l
(a) Structure:

Bonding: ' -.'.}'(.|{.{^.i...l11.,,||,,.l.it.

,l{ ,t'1 r'":,Y'

(b) Each Al atom contributes 1 valence electrons to its metallic bonding whereas each Na
atom contributes only { valence electron to its metallic bonding" Therefore, A/ has
n'nnil*, than Na as ther€
_:s:lii:"r,,. fol9r"tiuitv in A/than in Na"

JJC 2008 PageT of 42

3. IONIC BONDING

3.1 lonic Bondinq in lonic Compounds

Definition: lonic bond (which is formed by the transfer of electrons) is the strong electrostatic
attraction between the _
Figure 3.1 Model of an ionic compound: Lattice of positive and negative ions

ooooo Oppositely charged ions are formed

ooooo from the transfer of electrons from the

metalto the non-metal. Metals form
positive ions whereas non-metals form

ooooo negative ions to achieve a stable noble

gas configuration.

As shown by Figure 3.1, ionic bonding exists extensively throughout the entire structure.
Thus, ionic compounds are said to have giant ionic structure.

ln the giant ionic structure, cations and anions occupy fixed and alternate positions in the lattice structure.

Figure 3.2 lonic lattice of sodium chloride

CT
Na*

x The table below shows the chemicalformulae of ions of the first twenty elements.
|[ilt tv VVI vil

xDot.and-crossdiagramS(a|soknownasLewisdiagrams1ofioniccompounds

- a simple representation of the electronic structure of a species by showing the valence electrons only

Sodium chloride. NaCi -"].[,:]tJ-

[
Calcium chloride,CaC/2
-[ -
ca
[,i:,1 J'.[,i]'l
JJC2008 Page8ot42
 Common mistakes: Remarks
*[ .. - Since Na atom has already given away its valence
" -I
[ - lt" -l
ILI xxi J| |L:C/ :l
o. J
electron to chtorine atom toior:m Na*, there shoutd not
5e any crosses around Na.

.
ifill Ifh I Nooutercircre shourd be drawn

L\_-iJ t\../J
| 12* | o. I - Subscript'2'should not be used.
lc"l
t--J lt,^,'l
[';:'Jz Correctrepresentationis: [ .. l-f 12*f .o l-
.. J lc"l
lac/:l t I llcrll
t .. J

ExefQlse 3: Draw the'dot-and-cross' diagram of

(a) Lithium hydride

l ivv i I
-- j

-i

3.2 Strenqth of lonic Bond

I
x Strength of ionic bond is indicated by the magnitude of lattice energy.

Lattice energy of an ionic compound is defined as the enthalpy change (AH) when one mole of
the ionic compound is formed from its constituent gaseous ions under standard conditions.
[Refer to Chemical Energetics Lecture Nofes/

(Lattice energy simply refers to the energy released when one mole of ionic compound is formed from
ifs gaseous rbns.)

" e.g. tta*(g) + C/ -(g) -+ NaC(s) AH = - 77'l kJ mol-t = Lattice energy of Nac/
771 kJ of heat is released when 1 mole of NaC/ is formed.
=
+ 771kJ of heat is needed to break 1 mole of NaC/ into Na* and C/- gaseous ions.

Thus, the magnitude of tattice energy is an indication of the strength of ionic bond.

JJC 2008 Page 9 of42

 rx Magnitude of
9*x9- Compare with Coulomb's Law:
LE "c
It*r- orce
( where d = r* + 7- 1 11

where g+ and q- are the charges of the cations

and anions respectivery;
and r+ and r- are the ionic radii of cations and anions
respectivery.

Generally' {hs t 'r-or ' .r-''- the magnitude of lattice energy, the stronger the electrostatic
between the oppositely charged ions, the - : : ,,, . . , attraction
ine ionic UonO.

Two main factors affecting the magnitude of lattice

energy (LE):
(a) Charge of ion
The more highry charged the ions, the greater the
magnitude of LE.
(Electrostatic attraction between higher
charged anions and cations are stronger.)
e.g. Magnitude of lattice energy of MgO > MgC/2 > NaC/

(b) Size of ion

For ions with the same charge, the smaller the ions,
the smallgr the interionic distance (r*+r_ the
greater the magnitude of LE' (Electrostatic ),
attraction between small oppositely charged ions are
stronger as smaller ions can approach closer to
each other and they have higher charge density.)

e.g. Magnitude of lattice energy of NaF > NaC/ > NaBr > NaI

3.3

1. Volatitity
lonic compounds have r'-' ' |'melting and boiling points because large amount of energy
is
required to overcome the strong electrostatic attraction between positive and negative ions"
Melting and boiling points of ionic compounds
increase with the strength of ionic bond.
E.g. metting point MgO of
Table 3.1 Melting points of some ionic compounds in oC

$il IEF
MgF. 1261

fF-El fFBl lit

li;; ;;l li.lll'*'l fffi-f,] lcarz
Mzsl Hc_t
l:g
MgC/z
CaF2
714
1423
?g?Sl

2" ElectricalConductivity
i
Poor electrical conductors in
_ state because the ions in crystals are fixed at the lattice points.
Good, electrical conductors in i'| anrt
,.., !.1' :'' , ..
r'1\f. i, !r t I states because there are

Positive cations move towards the negative

cathode; negative anions move towards the positive anode.

JJC 2008 Page 10 ot 42

 3" Solubility

lonic compounds are generally soluble in water and insoluble in non-polar solvents (such as organic
solvents).
In dissolving ionic compounds in water, the strong electrostatic attraction between positive and negative
ions may be overcome by the ^-''y'.""*l\ :';-,+"':r, wh.en ions are'solvated by the
polarwater molecufes through the formation
-,- ).,released
o1 :'7- ?'\ €''o'!{l'' +'
t'.. : "

AHsoturion = - AHL"ti"""nurgy + AHnyor"rion

For example, when solid sodium chloride is added to water, an electrostatic attraction is established
between the ions (Na., C/-) and the polar water molecules. We call this attraction the ion-dipole
interaction. This ion-dipole interaction releases sufficient energy (known as hydration energy) to
overcome the ionic bonds between the positive and negative ions, resulting in the breakdown of the NaC/
crystal lattice and the solvation of the ions.
3.3
,-#
Figure How does an ionic compound dissolve in water?

I
.:t # s,;i $
lp -a *'
rr-n.^
*),,br
,,37rfr
J.
lv ,;d cr
I ";9 g,r ''5+
UI'
.J ! ";t,l re
(a) (b) (c)
lon-dipole interaction begins Crystallattice begins The ions are completely
to form: OF (of HzO) to break down. solvated. lonic lattice has
-
attratted to cations and H6* broken down and ionic
(of HzO) attracted to anions- compound has dissolved.

Figure 3.4 How does an ionic compound dissolve in a polar solvent?

lon-dipole interaction begins to

form: the posilive end of polar lons are

r solvent molecules are attracted

to the anions and the negative
end of the polar molecules are
completely
solvated by
polar solvent
attracted to the cations. These molecules.
interactions release sufficient
hydration energy to break the
ionic bonds.
Polar solvent
molecules

Condition for solubilitv:

Since ions can form ion-dipole interaction with polar water molecules, ionic compounds are soluble in water if
the energy released from the formation of ion-dipole interaction is sufficient to overcome the strong ionic
bonds.

With non-polar solvents, effective interaction between ions and the non-polar solvent molecules cannot be
established. Hence ionic compounds are insoluble in non-polar solvents.

JJC 2008 Page 1 1 of 42

 4. Hardness

The crystals of ionic compounds are very because strong electrostatic attraction must be
partially overcome to deform the crystal. However, the crystals
cfeanfy using a sharp-edged razor).
are _
(i.e can be cleaved

When a force is applied along a particular plane, one layer of ions is displaced
relative to the next.
As a result, ions of the same charge meet and repel one another, shattering
the crystal along the fault
line.

Figure 3'5 Cleavage of ionic solids: a layer of ions (a) before and (b) after force is applied

Force applied
\uI
n"r"
Repulsion btw
ions of same
charge Lattice breaks
down along a
layer of ions

Exercise 4: For each pair of substances, state which one has a higher melting point
and explain your
answer. (a) CaC/2 and CaF2 (b) NaCi and MgO
(a) Both CaC/2 and CaF2 have structure.
F- is To explain differences in
than Cf, leading to ionic bonds in m.p. or b.p. between
CaF2. Larger amount of energy is required to overcome the stronger
-- substances, always
electrostatic attraction between
_ and ions in than include the following in
the weaker electrostatic attraction between _ and ions in your answer.
(1) type of structure for
Therefore has a higher melting point than each substance.
(2) type of bondinq
(b) Both NaC/ and MgO have structure. overcome during
melting/ boiling and
Mg2* and 02- are in size and of -charge
than cOmpare their relative
Na" and cf respectively. Larger amount of energy is required to overcome
the stronger electrostatic attraction between
strength.
charged
and _ ions in than the weaker electrostatic attraction (3) comPare the amount
between charged and _ ions in of energv needed
and relate to m.p. or b.p.
Therefore has a higher melting point than

JJC 2008 Page 12 of 42

 4" COVALENT BONDING

Definition: Covalent bond is the strong electrostatic attraction between the

shared between them'

Cova|entbondisformedduetosharingofelectronsbetween2atoms.
are called bonding electrons. Two bonding electrons
Erectrons which are shared between the atoms
are not invorved in bonding are cailed rone electrons"
constitute a bond pair. outer sheil erectrons that
pair'
Two non-bonding electrons constitute one lone
xx a.
For examPle, I C, I C/ : Around each C/ atom, no. of bond pair = 1

xx ao no. of lone Pair = 3

by sharing electrons to achieve a stable noble

x octet Rule: Non-metallic elements form covalent bonds
gas configuration.
i
il Oxygen Water carbon dioxide Nitrogen
Nz
Hzo Coz
O2

ao xx .XX
o3Io H:OIH
XX
oo xx

tables for some examples'

Octet rule is sometimes not obeyed' See the following
(c) Aluminium chloride
(a) Beryllium chloride @ Boron trifluoride A/C/3
BeCl2
XX
nrX
X
XV,X
XX XX XX OX XX
IcrI ae! cl{ IcIIA/: cil
XX XX XX XX

The
than g erectrons in the varence sheil after bonding.
r' rn morecures (a) to (c), the centrar atom has ress
central atom in
.these molecules are saio'io ue and thus have a tendency to accept
"ieitron-o"ficient
covalent bonds' (See Section 4'2)
;;ilr;'ir"r molecule
"noinat
by forming dative

(O) Pnospnorus(V) chloride or

phosPhorus Pentachloride
Chemical PC/s
formula
aa
.O
or.l o ao
Dol-and-
cross
a-'O
o
.li" | "'f" ^to
'tl :it
oax"xaa-
diagram
';L'j ".ti:
onr o oo-
,Iiri.r'i.3
o-'a
aa

This
rn morecures (d) and (e), the centrar atom has more
than g erectrons in the varence sheil after bonding'
is called expansion of octet configuration'

JJC 2008 Page 13 of 42

-..-: ::::: _l
-3
 wilnmflflt,,tfllfllflt'
''{rlilltiilliii
llii:

x configuration:
Expansion of octet
The expansion of octet configuration is possible only if the central atom has u,,,,

to allow more than 8

electrons in the outermost electron shell.
e.g. To form PC/5, P must have 5 unpaired electrons.

nrrn
P: 1s2 2s2 2p6 3s2 3p3

3s 3p 3d
Only elements in Period 3 and
higher (Period 4, 5 ....) can expand
octet because octet is expanded
through the use of d-orbitals. The first
P*: [|-T-n set of d-orbitals is the 3d-orbitals.

PC4: TIIN
One of the 3s electrons is promoted to an empty 3d-orbital which is energetically accessible. With 5
unpaired electrons, P can thus form 5 bonds and hence PCis is formed.

Questrbn: Does NC/s exist? N: 1s2 zsz 2po | | 3s

For N, the next available orbital for the promotion of electrons is 3s, which is from the next prin6ipal
quantum shell. Promotion of electron to another principal quantum shell requires too much energy to be
feasible. Thus, N cannot expand its octet to form NC/s. NC/s does not exist!

Exercise 5:

Draw the'dot-and-cross' diagram of

(a) CCia (b) NF3 (c) CSz

4.2 Dative Covalent (Coordinate) Bond

Definition:
Hffind is a *gffiruHhl in which
@
x ln forming dative covalent bond, one atom is the drrfrrHraa ' ^nd the other is the *e
i#
For an atom to act as a-F4t must have

For an atom to act as anLt*it must have ffi

x Once formed, a coordinate bond has the same characteristics as a normal covalent bond. ln other
words,
the only difference lies in the way the bonds are formed.
x The dative covalent bond can be represented asfi&r (A is the electron donor; B is the acceptor).

JJC 2008 Page 14 ol 42

 i,i
I
l
Some Examples of Da :

Note: HgO'can also be represented as:

(a) HlEr-qlOL
oa
H't
l-
!.ot'H + H*
-_-_> ,:"f' ,,{ .r [x'].
A dative covalent bond is formed so that H can achieve the stable noble qas {He) confiquration.
i-i i
(nLNHr*Ab 1
,, N / -
:,t\4, -[
H._N-H + F-B-F ---> i\-i'Y !

I
F
I
-l L-
H

A dative covalent bond is formed so that B can achieve the stable octet configuration.

,
(c) AHrfrrof ,. r >
a''1,
ct c/ \
/ . :J

tl
A/_Ct + A/-C,
Li'
Ji

tl
t'

! .j. . .
ct cl

(d) Formation of #uring the reaction:ffi

i-J l/

H-N-H + .'H* -/ rr
ll -_ frvl-l-i
,
Fl
lr
El
tl

Exercise 6:
Use the concept of dative covalent bond, draw the structures of the products of the following
7 reactions.
(a) NH3 + A/Ci3 + ? (b) BF + NaF-+ ?
ir ii
f r-* \"
A'. *i'
tr
\,{ f\.-, I l'r
t-
I

n \- , -'
i
Jrj ! I

It )
n

f't'' i.,i,rl
ld,\lcvc'7c'''r
,Jl 1',;,11- 1, -. ' 1

i nr,,.' a a:i
i"**-
,i'.i''""1

'
Itre pur,.1 r,r r , JJC 2008 Page '15 of 42
r,vaurf 1s hq w^V
fvrlrlc'
o c\". I yc*vlX i-r, t
-
: 1i\,]{ i.nY rklL\r F s
 4.3 Strenqth of Covalent Bond
covalent bond strength is rerated to the bond energy. what is bond
energy?
Bond energy of a covalent bond is the energy required to break one
mole of b*o"ln
chemical Energetics LectureNotesJ"
atoms
gaseous molecule into constituent gaseous "o,,r"l"nt
[Refer to
(or, bond energy is the energy released when a covalent bond is formed
between 2 atomsr, fh;;;;;;6
The greater the bond energy, the stronger the covalent bond.
i J - .. , :

x Factors affecting covalent bond strength:

(a) Number of bonding electrons (bond order)
Bond strength: Triple bond > Double Bond > Single Bond
e.g. Bond energy: C=C

(b) Bond length (which in turn depends on size of atom)

For a fixed number of bonding electrons between atoms, when the Bond Length: the
size of the two atoms increases, bond length distance between
the covalent bond strength
and the nuclei of 2
atoms joined by
chemicalbond.
e.g. Bond energy of Ct--St > Br-Br > I-I
Table 4.1 Bond length and bond energy
Bond Bond length / nm Bond enerqy / t<.1 moF- Bond tsond lenqth / nm Bond energy / kJ mol']
ct-ct 0.199 244 c-c 0.154 350
Br-Br 0.228 193 C=C 0.133
'|51
6't0
l-l 0.266 0.120
C=C 840
(c) Bond polarity [Refer to section 7.3.1: potaisation of covatent Bond]
Polarisation of covalent bond such as 6*H--ct'- leads to some ionic
character. This ionic
character gives rise to-additional attraction to strengthen the bond.

5" COVALENT COMPOUNDS

x There are two types of covalent compounds which possess different physical
properties due to the
difference in their structures.
Most iovalent compounds have simple covalent (or molecular) structure.
some covalent compounds such as diamond, graphite, silicon and
silicon dioxide
-'.'-- (i.e sand, quartz) have \.'-
giant covalent (or molecular) structure. 3
The following diagram shows the difference between these two
structures.

Simple covalent structure Giant covalent structure

Example: carbon dioxide
Example: diamond
O:6-O I
o-c-o
; \ intermolecular forces
"' --z
---
o-g-O
/-/ :l'---'
'o:c=o Fl*l rro
covalent bond
\,

r represent a carbon atom i

Every atom is bonded to others by stronq
covalent bonds.
+ Covalent bonds exist extensively throughout
the whole structure, thus compound is sjiO to
have qiant covalent structure.

JJC 2008 Page 16 of 42

 6" GIANT COVALENT STRUCTURE
6.1

x Giant covalent structure consists of covalently bonded atoms at the

lattice points that can be extended
infinitely in three dimensions to form a giant lattice.

Atoms in giant covalent structures are held by strong covalent bonds. Therefore, giant covalent
structures
(a) have v"' "'''' melting and boiling points because large amount of energy is required
to
overcome the strong covalent bonds between atoms.
(b) Dol'r electrical conductors (except graphite and silicon) because there is no mobile
are
electron (charged particle) as allvalence electrons are localised in the covalent
bonds btw atoms.
(c) are n I olvrrz{ q. in all solvents because large amount of energy is required to overcome
the
strong covalent bonds between atoms.
(d) (except graphite) because breaking or deforming the structure
requires breaking the strong covalent bonds between atoms.

l 6.2 Diamond and Graphite

x Bonding and Structure
' Diamond and graphite have giant covalent structure.
In diamond, each C atom uses all its 4 valence electrons to form
4 single covalent bonds with 4 other C
atoms in a 'r:'lj- , !' i arrangement. (See Figure 6.1)
" '

ln graphite, C atoms are 'rlr'i]

"',"1.
-''
in flat, parallel layers. Each C atom forms 3
single covalent bonds with 3 other C atoms. The fourth unpaired valence
electron of each C atom is
delocalised along the layers. The parallel layers are held by weak van
der Waals, forces.
Csc i 'r1i
\-r ); i

Poor
electrical
conduction

Figure 6.1 Structure of Diamond ( . = carbon atoms) Figure 6.2 Structure of Graphite ( . = carbon atoms)
Electrical Conductivity
Diamond is a poor electricar conductor because there is r. i,- ('
) 1as all valence
electrons of carbon atoms are tocalised in the covalent bonds between
C atoms.

''i '' I - -'1 ; ;;; ;;" *i,r" a ;; ;1,;;;;

Figure 6.2) because
there are ]-;': ,' which are free to move .o, -,r the layers.
r.1 1 ",.
'What is the difference between these 2 terms: delocatised electrons and mobile electrons?
i.D.elocalised
electrons: they are n,ol-fixed at a position but are free to move to a certain
extent- ]
' -
they are able to move freelv in anv direction . I , "*
iMoDf le efectrons:

x Hardness
Diamond is v-.lY 7'
because breaking or deforming the structure requires br.eaking of the
strong covalent bonds between C atoms.
Graphite is 'l"i-
because the layers are held by van der waats' forces which are inr\ ' '
enough
to allow the layers to slide over each other. This makes graphite
suitable for use as a l rbricant.

JJC 2008 Page 17 of 42

L.-=
6.3 Silicon and Silicon Dioxide
r{'
Silicoir has a giant covalent structure similar to that of
diamond. Each Si atom forms 4 single covalent bonds with
4 other Si atoms in a tetrahedral arrangement.
Silicon is a semi-conductor with a high melting point of
14100C.

SiO2 (s/rca, crystalline form in quaftz, impure form in sand)

has a giant covalent structure. /\.
Each Si atom forms 4 single covalent bonds with 4 oxygen (.
| Silicon atoms I
silicon atoms) I o oxvoen atomJI
atoms in a tetrahedral arrangement. Each O atom forms 2
single covalent bonds with 2 Siatoms. Figure 6.3 Structure of Silicon (left) and
Silicon dioxide (right)
Silicon dioxide has a high melting point of 1600oC.

7" SIMPLE MOLECULAR STRUCTURE

x Most covalent compounds have simple molecular structure (also known as simple covalent structure)"
x In solid state, simple molecular structure consists of simple discrete molecules at the lattice points.
WITHTN the molecule, atoms are held by r :!'1'.) \ !I :i\ 1"
t ''r : "
BETWEEN molecules, molecules are held by ' ;' '*-.' i
' -

7.1 Phvsical Properties of Govalent compounds with Simple Covalent Structure

1. Volatility F Metallic bond, ionic bond and

Compounds with simple covalent structure have covalent bond ate strong
melting and boiling points (high volatility) because little bonds. Thus metals, ionic cpds
energy is required to overcome the weak and cpds with giant covalent
structure have high mP and bP.
between the molecules. Melting
and boiling points of compounds with simple covalent structure ) lntermolecular forces are weak
increase with strength of intermolecular forces. forces. Thus cpds with simPle
covalent structure have low mP
Note that the covalent bonds between atoms within the and bp. a
molecule are not brsken during melting/boiling.

2. ElectricalConductivity
Compou"nds with simple covalent structure are poor electrical conductors in any state because there is
.''.;,' f ., li ':, . t " ":' l'.'
NO i-
(Exception: For polar molecules which react with water to form ions, the resulting aqueous solution
conducts electricity because of the presence of mobile ions. E.g. When hydrogen chloride gas is added
to water, H+ and Cf ions are formed. Thus, the resulting hydrochloric acid can conduct electricity due
to the presence of mobile H' and Cf ions.)

3" Solubility j t

Non-polar molecules are generally more soluble in non-polar solvents such as hexane, benzene
and methylbenzene. Polar molecules are generally more soluble in polar solvents such as water"

4" Hardness
Compounds with simple covalent structure are soft because breaking or deforming the structure only
requires the breaking of the weak intermolecular forces between molecules.

JJC 2008 Page 18 of 42

 7.2 Shapes of Molecules
x Can be predicted using the Valence Shell Electron Pair Repulsion (VSEPR) theory.
x VSEPR theory states that
(1) electron pairs (i.e bond pairs and lone pairs) of srtral -) Determines the arranqement of
electron pairs around central
atom arrange themselves as fat as,possible in space
atom.
to minimise mutual repulsion (see Table 7.1),
(2) lonepair-l'one pair repulsion > lone pair-bond pair Determ ines the @tion oflone_.rejt
repulsion > band pair.bond pair repulsion, as well as bond anqle.
\
(3) multipte bond (i.e. double bond or triple bond) is 1 (r if-rl ' r ioi; .r-t
^
treated as a single electron pair. I 1
I
y;t
-i:stf )

Table 7.1 How electr:qn paiii will anange around ihe

:;G*= eailiilltfito minimise their mutual repulsions (VSEPR)

?electron pairs . $-blectron pairs 4\lectron pairs

Dr0
7

r,,1200

.\.
''
i,!-.'- ':i.,".., "r' r:.' 1:
"':'
. .^,!''
Arrangement' \r J; rr 1{ Arrangement:
',{,"l^."
Arranoement' rt-r

t
lectron parrs -@etectron pairs

t
I
_L_
I
I

P1b';l; :)'!.', i t/;' t,_ t",

Arrangemeng TP i 6o!'lAL Arrangement:

r rr:':- i i
?.r t

JJC 2008 Page 19 of 42

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 ln an ammonia molecule, there a electron pairs on the central N atom. The electron pairs are in'a
tetrfdned,fal arrangement."r" Since tnere are 3 bond pairs anO \ lone pair on N, ammonia is
with bond angle l0*o because the \-$A&ltslY: l!- repulsion is
greaier than the L$/d\r'v*b0,trlhd\v
repulsion.

In a water molecule, there are +

electron pairs on the central O atom. The electron pairs are in a
tQ\\AWdYaf arrangement. Sinc,e th.erg.are L bond pairs and L .lone pairs on o, water is
crr4^r4// Jo.J U*C4"fu"."u"" n"
tolnrePttrz-'tqa-etailrz repulsion is greater
than the
""gli repulsion, which is in turn greater than the
repulsion.

Exercise'8: By considering the no. of lone and bonding pairs of electrons, predict and draw the shape of the
following molecules or ions.
(a) QSz a B 6G .t\r[, iE, $
4'e '
al
'i o''
(
l-o ,t
r--)
e
o
-I. x1

(b) 'tFs sb\l /t''\.

-l
t1 !\r: :t'
.l' :
"i
'i

j l*
t

*-\

(c) H.Q* I
,t *-\ .t
t
!

fl
i
!
:
I E:
th
l '\
\:) -'
I

r
i*i ..r_".-
;:-':.... I
f
.
:
i_l 1
i-i

-t-

(d) IJ r--{
li
ll-1
-t^l
,r-, \ l Reminder:
:-L' -*\ "' .; iinf,a"
,'i'',.,j -'' ',
.
For electron pairs
| ! \t l' arranged in trigonal
\.\1
\",ir bipyramidal manner,
1
t the lone pairs are
I always placed at the
"1
t equatorial position
to minimise repulsion.

JJC 2008 Page 24 of 42

!1.{:,,',C,tt .
"*t-,,uf
 7.3 @
Pure covalent and ionic bonds are extreme cases. In reality, most compounds have bonding which is
i

7.3.1 lonic Characterin Covalent Bond - M

x|Gi$€h{aGl9rinacova|entbondistheresultofthebetweenthetwo
atoms involved in the bonding.

"iE{'@o
Between two atoms lf the elalmgtetiulty of the two atoms is lf the da**qnll*ty of
witfrci*iler.(*rue) #!da#elent, ldr*don occurs as the two atoms iscq;.
d-tnmget&uity, the [hs el*r'an Glgul will be ehi&edmore towards diffffirt? the deltrum]
electron cloud is the@ would ber;rptuifi
@y. Hence, the more electronegative atom. tnnfsmed tr the more
a acqu ires aSrcharge (pc**'.rccnergc) wh ile elrtmgufi+aqatem.
J This results in the qlgLtt'W"J+ivQ > cr reg
formation of a mr the less electronegative atom acquires a.A*
charge (p.*C*n h.f3e). + dipde
This results in the
.t,C

ffi F:r,"t4 formation of cation and

anion. Hence, an*rni*-
Such a covalent bond would thus have some
iricrlaracleJ pufnntunt
and is called a
bilftls formed.
,hnrdpor in shbrt, aprhhtd.
xUsua|ly,ifthecovalentbondisformedbetweentwn"dirnrre&-etoms,the@
Exception: C{4*,S,s4,$H bonds because the electronegativity of 6; H, F and S are simi{ar.
> hoh^4o.\ c.ovoJc-qfi1""r,1n7,
x Presence of ionic character in covalent bond affects
(1) the sgtbof the covalent bond (see Section 4.3, page 16), and eX-{+adtrD, sl+e-,r^q{nenV,A&l -
(2) the neta*'of in'!ffrnslcsntarJa-ee: bcbr r{Fs-mcffrles (see section g).

Example: J91 P2 O2(b)

Bond Bond energy / kJ moFr Bond Bond enerqv / kJ mol-'
H_H 436 H-H 436
a P-P 208 ct-ct 244
P-H 322 H-C/ 431
The P-H bond energy is the mean (average) of the H-H and P-P values. Explain why the H-C/ bond
energy is not the mean of the H-H and C/-C/ values.
Because the electronegativities of H and P are similar, P-H bond formed will be
hdn-Po\oY . As such, the p-H bond energy is the average of tJre H-H.and p-P
values because all three bonds share the same characteristics of being non-polar. ln
comparison, H-C/ bond is
Sqt (due to different electronegativities of H and C/)
while H-H and C/-C/ bonds are non-polar. The presence of slight ionic character in H-C/
bond stvtv''qtngn I the bond, giving a bond energy higher than the mean of the
-
H-H and CI-CI values.

tEat t'o"l I Large extent of polarisation can result in weakening of the covalent bond.

JJC 2008 Page25 of 42

 7.3.2
x

anion towards itself. The cation is said to be polarising the anion.

between the two ions, and gets shared by them.

lonic bond with
covalent character
the electron cloud is being shared between Af* and O2-.
x This concept explains why beryllium chloride and aluminium chloride are essentially covalent as C/-
to sreater polarisation. Note that Beo and A/zor are essentiallv ionic due
"uoj".ted
*g5,r#:Ti":3r:t,:l:
x The degree of covalent character in an ionic bond depends on the extent to which polarisation occurs,
which is in turn determined by:
(1) the polarising power of cation hoW paqgpa c-m 7A?AW L^Ardr\t cAvAck d?
Cations with charge density (i.e. small size and hiqh charge) can polarise anions to
S
greater extent. "
E.g. charge density of cations: Na* Mg'* < A/3*
-
Degree of covalent character: NaC/ < MgC/2 < A/C/3

(2) the ease of polarising the anions (polarisability of anions)

anions are more easily polarised (more polarisable) by cations.
E.g sizeof anions: ;nc*<cta'thal. F- < Cf < Br- < I-
Degree of covalent character: A/F3 < A/C/3 < AlIs
< A/Brs
-
If,ts ,s why AICQ is covalent while AIFa is ionic ( F is less polansahle ).

7.4 Polar Molecules

x The presence of polar bond(s) in a molecule does not necessarily mean that the molecule is polar.
--
E.g. 1: CO2 molecule is non-polar even though it contains polar C=O bonds. 3
o-c-o5+
5- b-
A
++_+ non-polar molecule is
where overall dipole moment of
one

Rsason:6- and 5+ charges of any polar bond produce a dipole

the molecule is zero. (Either
because there is no polar bond or
(separation of charge, ie presence of 5+ and 5- charge) the dipole moments of the polar
which has a dipole moment p. Dipole moment can be bonds cancel out each other.)
understood as the magnitude of the dipole.

In CO2, the dipole moments cancel out each other because the dipoles, with equal magnitude, are
acting in opposing directions. Thus, CO2 molecule has
and hence is

E.g. 2: BF3 molecule is non-polar even though it contains polar B-F bonds.

6- F\ The dipole moments To determine overall dipole

\6+
B_F 6_ cancel out each other. moment, treat each bond
dipole as a vector, and sum up

ur/ JJC 2008 Page26 of 42

all the vectors.

I
--
lr x Tqche@
Does the molecule have polar bonds?

Motecule is non-polar.

Some other examples:

(a) PC/F

PCG is a non-polar molecule

because the dipole moments
cancel out each other.
>
J

(b) sFq

SF+ is a polar molecule since it

has an overall dipole moment.

(c) SFe

SFe is a non-polar molecule

because the dipole moments
cancel out each other.

-
(d) rFs

IF5 is a polar molecule since it

has an overalldipole moment.

(e) XeF4

XeFr is a non-polar molecule

because the dipole moments
cancel out each other.

Note: lf the central atom has no lone pair of electrons and is bonded to only one type of atom (e.9. CO2,
BFs, PC/s and SF5), the molecule is non-polar because the dipole moments would cancel out one
another.
JJC 2008 Page27 of 42
Exercise 9: Determine whether the following molecules are polar or non-polar.

(a) HzO

(b) cc/4

(c) CFC/3

Dipole moment of C-F bond is greater than that of C-C/ bond because the electronegativity difference
between C and F is bigger than that between C and C/. Thus CFC/3 would have an overall dipole moment
and hence it is a polar molecule.

(d) IC/3

TRY THIS: J97P3Q3

The diagram shows a liquid flowing from a burette and a charged rod
being brought near the flow.
Which liquid would be deflected as shown?
A bromine
B cyclohexane
C hexachloroethane -ffi --nieoatiueucr'giig9{
rort

D trichloromethane

JJC 2008 Page28 of 42

 8" INTERMOLECULAR FORCES (IMF)
x Recall: Simple Molecular Structure
WITHIN the molecule, atoms are held by strong covalent bonds.
BETWEEN molecules, molecules are held by WEAK intermolecular forces.

Three types of intermolecular forces: Strength of IMF

(ID-ID) wQql'( +
(1) Induced dipole-induced dipole attraction
-{ (comparing molecules
with similar M):
(2) Permanent dipole-permanent dipole attraction (PD-PD) i*\,.$: $it"",' ID-ID < PD-PD <
(3) Hydrogen bonding ':Jvo$Qt1\'if, hydrogen bonding

The strength of the intermolecular forces between the molecules affects the
(a) Melting and Boiling Points
When compounds with simple covalent structure are heated to melt or boil, it is
the
which are overcome. See Figure 8.1. (Covalent bonds are not broken!!)

The stronger the lMF, the ht the m.p. and b.p. of the covalent compound because more
energy is required to overcome the stronger lMF.
C
tf
I
.b
I

.b
tf tf tP
Figure 8.1. Boiling of water. Note that the covalent bonds between atoms are not broken.
Only the weak intermolecular forces are overcome.

(b) Solubility of the covalent compound (?)

polar covalent compounds are more soluble in qltleov^s
Non-polar molecules are soluble in
sofuents.
solvents. Molecules which can form hydrogen bonding with water are expected to be
more soluble in

e (PD-PD)
8.'! Permanent Dipole-Permanent Dipole Attraction
tB -.a permanent dipole moment.
A polar molecule has
xThee|ectrostaticattractionbetween3rr|*wlusisknownasthen.'#
JiFi-.lErdiaD (o r nteraction).
i

permanent dipole - permanent dipole attraction

a
a ,/
,/\.G
,/\6+
\j\ a
I

6+

JJC 2008 Page29 ot 42

:::=.-:a:
 t.a\ t."\- .t\^_
^
*/T= (;;/z=* ) ,f23.:e-
permanent dipole-permanent dipole attraction

x As the magnitude of the dipole moment increases, strength of permanent dipole-permanent dipole
attraction 'tf'}{n'Qo| (molecules which are more polar are held by stronger PD-PD).

8.2 Induced Dipole-lnduced Dipole Attraction (ID-ID)

|rWareheldtogetherbyinduceddipo|e.induceddipo|eattraction.
x How does induced dipole-induced dipole attraction arise?
Non-polar
molecules
e.g. Br2, (a) Distribution of electron cloud
CO2, He should be even for a non-polar
molecule.
G

(b)

o'
However, at a particular instant,
uneven distribution of electron
cloud may occur due to the
continuous motion of
electrons in the molecule.
temporary This results in the formation of a
dipole temporary dipole.
ID-ID attraction
(c) The temporary dipole induces
(a* 0-/I )
another dipole in a neighbouring
molecule, resulting in the
formation of an induced dipole.
temporary The attraction between them is
called induced dipole-induced
Qiu-
dipole
dipole attraction.
{.

lnduced dipole

ID-ID attraction and PD-PD attraction are commonly known as van der Waals' forces.

Factors affecting the strength and extensiveness of van der Waals' (VDW) forces
(a) Strength of VDW forces depends on the number of electrons in the molecule.
When M, of the molecule increases, the no. of etectrons in the molecule lr\A$+ . As the
electron cloud gets larger, it becomes more polarisable and the strength of VDW forces between
molecules rnenl)t95

(b) Extensiveness of VDW forces depends on the surface area of the molecule.
(For molecules with the same no. of electrons) When sgrface area of molecule increases,
VDW forces between molecules become tl^s\ 1€v as there is greater surface
area of contact between molecules.

JJC 2008 Page 3O of 42

 -I

Exercise 10: Describe and explain the variation in the boiling points of noble gases.
. All noble gases have *qufu structurd with
between their respective

As the no. of electrons rnCr<r'tSQ-l down Group 0, the strength of

vV\) tsrbt tvu,v?qV down the group.

. Thus, down the group an increasing amount of energy is needed to overcome the
v\lw ftvr4 between atoms and hence, the boiling points of noble
gases rvr rrv0A )&

x For organic compounds, branching of the carbon chain causes the molecules to be more spherical, hence
reducing their surface area and the extensiveness of VDW forces between them
branched organic compounds have a lower boiling point than their straight-chain isomer.
=

@l:Exp|ainthedifferencesinboi|ingpointsofthefo||owingisomers
-t x tt
H-C-ll
- I
l*-g-fl
a
fi-c-H 'r|
't
I
I
lrc-H H-f-x x *
tl trl
"F9-"
I g-g+C-ll *lt
x-c-rt tl rtl-c -c
I
lFe{ n-*i-rr H
''e-cH#-n H
I
I I
X. il'. lt'
pentane
' ? methylbutane 2"2dimethylpropana
b.p.36'C . b"p.28'C b.p. 1S'C

2-methylbutane molecule has a surface atea than pentane molecule due to

of carbon chain. As a result, less energy is required to overcome the
between 2-methylbutane molecules. Hence 2-methylbutane has a
lower boiling point than pentane.

2,2-dimethylpropane has the lowest boiling point because it's molecule has the smallest surface area, and
hence, the VDW forces exist between the 2,2-dimethylpropane
molecules.

8.3 Hvdrooen Bondinq ,. s\rt\r;1 ir-\ -('t \ b\;v{l\L 'i

x When a H atom is {;s!!y bonded 1s s F$hty'^'^.trrnr! (such asf;€*llfa *fdhCe
is produced in which the H atom acquires 6+ charge and the electronegative atom X acquires 6- charge.

x This particularly strong permanent dipole-permanent dipole a molecule and the

l^^^f^;- r v6'^r "nolher molecule is known as E4[ggtlbtlding:
Example 1: Hydrogen bonding between H2O molecute{-ft$L\
lliifiGft1w" ,"6" 7 ,rti\rr.rirZ* rzrt
\

./ .-\ i xc.,
H H-'- - - - {o^
! !-! tl,
-d\ 1r'

Example 2: Hydrogen bonding between NHe molecules i\M,'vruNv\

Ji H Hlr
*,\$i /
A

/'"Y\ ,- 1,.
iilcl\l\4"'-i^ [] H
5+ n w)\' {' JJc 2oo8 Page 31 of 42
 criteria for existence of hydrogen bond between molecules
(a) a H atom bondedrulltEtly to a
(b) at least a pairof lc*r*5cn
@(F,
the highly@
o or N only) ffi**
6-o6-*
where X, Y F, O or N
@ing on physicat properties
(a) Boiling point (and melting point) of HF, H2O and NH_3 are unexpectedly l,r\tlu
the presence of ltvrlr,.gr i.rtun"ri.", vr-*e\,-e,l befw due to
rn their molecules.

For molecules
p
with similar Mr,
d strength of IMF:
{ H-bonding >
c PD-PD attraction
> lD-lD attraction

rI'

Numler of,piriod' Nualrrolpsr-id<|.

(b) So|idiceisl€[5..dense.thanliquidwaterbecausethetweenH2o
molecu|esresu|lsinicehaving.anflfFErlg|^+ll'^Eachoatominso|idiceiSffio
ttltuttt*nd!h"''^g r'brrC '+^ +.-^ ^*'-^r ll"t"tt'O ln arlla|16l manner.
tv rU\-lv\€ €{
e{prrti 1

In water

(c) compounds capable of to be s5:

s.o\ulble
. _forming hydrog.en_ bonding tend
E.g. NH3, carboxyric acids (RCooH;, atcorrJs (RoH)
with
"ni "riner.--
Example 1: NH3 molecules form hydrogen bonding with water molecules.
C t,43 t:lv,trtr? ir,rvv"-r{- e-
H
\ r- - Ht)-{
\ .t*-*{ ^
\
H
H
-tt' Y-,
\ *")r..
n{1rl
,/^ ^o':
/<^/
H \ /''u
\/H
ti.{rtr-i-e..^!c*crl j'"
Example 2: Alcohol (RoH) molecules form hydrogen bonding with water molecules.
R - JtH
/\,C*
\ \vv:/.+t ./
Xts
\ qx
ln*, -: xot
Ox
/n^ \ ,/\
/f'
H
HR
H J+
JJC 2008 Page32of 42

=\aui \ur'"1crt r.:\€r_.J;i'. €fiu,. {.1'*L -l!t:.\*p*.h:.,r,,\r,1 ,-t- r'r,r t..'{ h]< icil,11v* 1,'1
r_ p1{4r
 (d) M, doubles when cr-fln3s C*
monomer

#of the dimer will

be €fi: that of
hydrogen.bonding JFt€iffiFtI.

oi*u,i,"tio willform
the carboxylic acid molecules
;ffiilffi;if*i#*'Xt*"t'",
"

.o hydrogen bonding
y^'*wfl€* . l^V '*L !!^"*1-- t t't '' I

/ ( *] -1',;'l-1 : [,]'
c,,
( a-r/
\6+ 3\ As rt Y'.)rc lrr;r^''1.
:' \'f, t
H

F ln some compounds, functionalgroups are so oriented that hydrogen bonding can take
place between
them**.'|etoformintramo|ecutarhydrogenbonding.Thiswouldhaveanimpacton
their mp and bP. For examPle,

o
V' I
A intramolecular
\ \of
aa
\--/
hydrogen bond
-/ t( )l
o.zH6+
o-nitrophenol
i \
re\S \t[\1 t;
h,r'J, w{ta'J, r'" gv
.

J..Jf tL'r,fE\ -i r-i:--"{\6-{,,

Y o\
H
i'r:.-,J t --i\ t., i; i .\.j
p-nitrophenol
-rfl,:,lf--
After forming intramolecular hydrogen The -OH and -NOz grouPs are too
bonding, the H atom is no longer available for far away to form intramolecular
F
intermolecular hydrogen bonding with other hydrogen bonding.
o-nitrophenol molecules. Hence, p-nitrophenol will have a
Hence, o-nitrophenol will have *5ftbo (than o-nitroPhenol) due
(than p-nitrophenol) due to lcer*nic to#
@ct&:.

Exercisel2: Explain why the boiling point of water is higher than that of (a) HzS and (b) NHg.

(a) Both comPounds have i.O\Y-trn\r-. . A larger amount of energY is

needed to overcome the jt!*s" between tlz,D ,molecules
than the l^..'€, it-x,- u- t$rz'
between
f-r , i Therefore, b.p. of water is higher than that of HzS. f \ u: ie.
rr"f
r.''\ i
'-
f' r ';-'
"*rl"r.
6"u" livufl € rxrtt f t ur uV strUCture with .^^''{ tCl'+ t+;l' lit - r:i ..
''rfu'
(b) Both COmpOundS
between their respective molecules. A larger amount of energy is needed to overcome
tne
f-r{',r',tr,:.r r"\.Tlr-rl(,v l-:rr',',1 between HzO molecules than that between
NHg mo'lecules as the O-H bond is r,v.i.N.(,, polar than the N-H bond. Therefore,
b.p. of water is
higher than that of NHs.
JJC 2008 Page 33 of42

a
9. GOVALENT BONDING: INVOLVEMENT OF ORBITALS
9.1 Overlap of Atomic Orbitals
x ffitflEnd is formed due to the sharing of electrons between 2 atoms. Since electrons are housed in
orbitals, formation of covalent bond involve%
x The electron pair in the overlapping orbitals is shared by both atoms i.e. bonding electrons.
x The the

9.2 Tvpes of Govalent Bonds

xThereare,whichareformedbydifferentwaysofover|appingtheorbita|s.
i. @formedbyhurlrmd6oforbitals)
Head-on overlap (or head to head overlap) results in the formation of sigma bond (o bond).

E.s. (i) H2: +H ) H-H

,,^
[.1
\-/
1s orbital
>4\1
(ii) F2: --t v - t z
+F
i_.\ r,,l
't,'.1
2p-orbital i--

t-t ,l'i"
rr' H
.-

i t>'i l .,; l1^r'

1s orbital 2p orbital Head-on overlap of 1s and 2p
orbitals

ffi)(formedby of orbitals) '-ie.y\'1[, | /

tl
ffkp \iiA: ')""
Sometimes, after a sigma bond is formed between the two atoms, the p orbitals of '-:v'\'{ !-u,
the 2 atoms, that are parallel to each other, also overlap sideways (side-to-side v'€ 'i' -r"-' '
overlap). This type of overlap results in the formation of a pi bond (n bond).

(i i) N itrogen 1'l s22s22p,1 2prt 2p.' )

]fo 5
- '- i -i ii
* '- l'i fi
Nz:molecule

o.r,,molecule The two-

'ro 3n form a -rb.rd The ftrnFr€|filake
The rrbilale ricrtF l-re' ^^ to
.form The twcflpTuf*c|e overlap Similarly, the two rffr*te.overlap
-$ond. ar5.r#
sideways to form Jialrcys to form another#
Hence the tnnx|gs,elms are bound Hence the two nitrogen atoms are bound
together by a iltbtFbuftl (comprise of **- together by a triple bond (comprise of 1 o
.551lrt anrt Arrbrd\ bondand2nbonds).
lr i-;v*'\ - ,j trl
JJC 2008 Page 34 of 42

$[. '{
/. The extent of overlap of orbitals in a n bond is t€ JJ than that in a o bond. Thus a n bond 1. u'i'tt -'
than a o bond.

R 1n sll"ngttinla hnsJs, ruf the bonds is artl{r+C and thest are-*.nt

E.g.

Each N-H bond is a o bond

\"fi,
--?FV C=O bond is made up or ^-t r bsnd and orrrbend
fi" oc=t

N:N N=N triple bond consistof emrorb*d and ttnd:ndo

-

9.3 tfff*r of Atomic Orbitals

x ln 414gugi6$ng6g{Jles (e.g Oz, HF, N2, etc), a#end is formed by erndrnffV'€ftn*@|HlHffl'
a CantheSameconceptofatomicorbita|overlapbeapp|iedtffisz
Consider*elrwhichisa-culewithtwoequalBe_C/bondlengthandstrength.Whichatomic
orbitals of Be could be used to overlap with the 3p orbital of C/ in forming the Be-C/ bond?
r(** B€ *-- C-f.
22pu3s23ps
Be: s22s

u
1s22sz 1

Be:
(gffitf state) 1s
ul-T-t--l
2s 2p
CI: u
1S
rurtmm
2s
runmilTl
2p 3s 3p

Be*:'
(r5r{ette)
M nnr-n
1s €.'/ zP
l'.,-:/.1-,1
I t,
1
:,, ..1

.t.
-t
mtl ,e+*f*,\
sp hybrid orbitals
1

- a.l
i.( i .,' .,:,li
To form two covalent bonds with Cl, Be needs to have two half-filled valence orbitals. This can be achieved
by the promotion of a 2s electron to an empty 2p orbital. Note that while 2p orbital is directional (pointing in x,
y ot z- axis), 2s orbital is non-directional (spherical). That means one Be-C/ bond will point at a definite
direction (say z-axis) while the other bond points at some undefined direction. This contradicts the linear
shape observed for BeC/z molecule.

Toresolvesuchdiscrepancies,roi9proposed.Thistheorysuggeststhatbefore
c5*efiqrfa5i13b occurs,.l#lrof the ddrfrl arecl-to produce a new set of lfrr
filrElf
Note: No. of hybrid orbitals generated = no. of pure atomic orbitals used in hybridisation

JJC 2008 Page 35 of42

x lQpesoffrryenHisat$oa:
(a) €p.@r{d4tmtioD'.trg.and *|lor[ital undergo hybridisation, forming @io
r;yhisit spstl€sto each other.

3F,6,,,
Ones
*'$,.*#$
One p Trrs ttr cibital:
$riapq,
..'_!-
4o
r\t
-,
exanrptr,,

- 3e-
r
Cl

(b) .ge&{ry*#t$#*rn: flises*.r6 .f,m*tr{trtiitals undergo hybridisation, form ing thr.nqrlfri#efit .sp2
nyn**"e**ta*s, which are4*&\o each other.

sro.{ffi--& A
Sna.*-.. ri*o.p ct/ \cl
c/

B
I

' i--flftrF
n'4fi)1"
(c) qA"tq*!a#i6{a: m*and thprcrbifr*ls undergo hybridisition, forming fxeqd*n6.ep3
hytriAerhitals, w h ich a rsq€€€$ 1e
. each oth e r.

:-+:tQQ* ,fl:
M i
'r' Y""'
.

spr etJCC*
@ "7\ n;f-H -$r

t,
O.trs
toc
*ri*d,p:: f*ur,srt',offiais, (meth-ane)
'''r,f Ltt'i,,ifit
i
1'r'r,1,",t-\ n.p-rr-.: ,ntttLlr C(i''L* t)

x How to determine the state of hybridisation for the central atom?

1. Draw dot-and-cross diagram.
2" Determine the number of electron pairs (bond pairs and lone pairs) surrounding the central atorh.
(multip|ebondisregardedasasinglee|ectronpair)
Match the number of electron pairs to the number of hybrid orbitals needed. L

Number of e No. of hybrid State of Arrangement of hybrid orbitals Angle Example

pairs around orbitals hybridisation for between
centralatom needed the centralatom hybrid
orbitals
2 2 sp Linear 1900 BeCl2
3 3 sp2 TrigonalPlanar 1200 BC/3

4 4 sp3 Tetrahedral 109.50 CH+

5 c sp3d Trigonal Bipyramidal 1200, goo PC/5

6 6 sptd2 Octahedral 900 SFe

JJC 2008 Page 36 of42

--
-7 EXeIgjSe_I3: Determine the hybrid state of allcarbon atoms in the following molecules"
(a) CO2 Note: Only the orbitals
of the central atom
undergo hybridisation.
/sP
o-c-o

(c) CH2=CH2 (d) cH3cooH

Hr. ,v- '.f'

\^=,( ,f |
H-
y'Y-'\
HH vtA

9.4 Hvbridisation in Methane. Ethane. Ethene. Ethvne and Benzene

Molecule Shape Hybrid Hybridisation and Bonding

State of G

Observations / Facts:
Methane ;fcar*e*al .#,
.CHa . tetrahedral molecule with a bond angle of 109.5o
. four C-H bonds, identical in length and strength

'@. m u
(s#&dc) 1s 2s
ffi

€s:
krtits[sKq
m n
1s 2s 2p

'te

The four atomic orbitals (one 2s and three 2p) are mixed to give '1.
new, identic"l 5$r" hybrid orbitals, each containing one electron.

4 sp3 hybrid orbitals of C atom qffl**..dsn with 1s orb1al of H,

forming#
H
|l/ {€eE
:
H<C\--
--__\.' H
H
signifies bonds into the plane of the paper
tetrahedral
\\$rr"'
> sigriifies bonds out of tbe plane of the paper

signifies bonds on the plane of the paper

JJC 2008 Page37 of 42

.-:
Molecule Shape Hybrid Hybridisation and Bonding
State of C

Similarly,
Etlfdfie .lFctmhskak
CzH. with "d'" Each of the two carbon atoms has 4 sp3 hybrid orbitals.
respect to
GhG
calem,,*
\_s,*u.
/,-Y'
1 ep1.&ybrid.,ff,b.ltal of C atom qrm@,,&ead-on with the c*? ayurio
orbital cjf anotherGetom, forming *,@.,eM.*
The rest of the $*ry4**erffib.@f,,ffi,#l,C atom o*psaadon with
1Sffi,s*r**,,forming a totalof$G** Meb in an ethane molecule.

Effile -@ .ocp?
Observations / Facts:
Qsf+ TlEnar with . trigonal planar molecule with a bond angle of 120o
respect to
o four C-H bonds, identical in length and strength, and a C=C bond
eafr?q
elffib
(molecule
is planar, (ground
C:
state)
EM
1s 2s 2p
flat)
c*r U n
(excited state) 1s

3 equivalent spz
n
2p orbital (unhybridised)
hybrid orbitals

Three atomic orbitals (one 2s and two 2p) are mixed to give J new,
identical Q:r
hybrid orbitals, each containing one electron.
Thus, each C atom has one unhybridised 2p orbital and three equivalent
sp'hybrid orbitals.

H
H\ /rH/t'o'
', o,,,,.
%,....,rrr\\ l^-l^
v-lr, \1
l

^/@), H/ ffi,YH
f ry?*hyb*iC-'esital of C atom eiruh€E*#ead€n with the'se&'+r$l*
orbital of another C atom, forming 3 @@u*brend:"r
The rest of the.s*?*ybrridbditets of each C atom exsls&cadeon with
desb*tsrkef,lJeforming a totalof 44*H,*&efigein an ethene molecule.
The renh$riCe*,"gpr'*€itfta+*tfl€"ttom mdrpc',git*G{ffiy with the
.JJllbldlEidi€n4l''-8*:',,sbi&d " of another &*rl€H, forming a@
rbend"(electron clouds lying above and below the plane).
JJC 2008 Page 38 of42
 \

Hybridisation and Bonding

Observations / Facts:
Etryp . linear molecule with a bond angle of 180'
$#z r two C-H bonds, identical in length and strength, and a C:C bond

C:
(ground state)
u utflTl
2s
1s 2p

C": M NMTII
mm
q/-J2P
(excited state) 1s

2 equivalent sP two 2p orbitals (unhybridised)

hybrid orbitalq

Two atomic orbitals (one 2s and one 2p) are mixed to give
2' new,
identical &, tFnyOtid orbitals, each containing one electron'
Thus, each c atom has @ (2p' and 2pr) and
2 equivalen! sP hYbrid orbitals.

Planes at righl angle

@n
c-c H-C- c-H
€ 0.'120 nm

. 4|!!*|.Iid c atom .tlrltprh.-Lon with theaphtbddnrlilel

orbital of
of another€atern, forming a€.Cclerd-
o The remaining ee*bliarc$ital ofrssglF€ atom cnrlaFr&erton with
{S,ltlitrtcfH, formingl€ullalggg$ in an ethyne molecule'
. SilrrliteLntrD atom dtEfElEriir!f;lv with ?trt?urbil* of..anotheF9
. atom. The same appties to ne pair otinq9dda..dsf,r.rbitals, giving
tvvo&C*&9ldgwhich are pltpailludB{ to each other'

JJC 2008 Page 39 of42

Molecule Shape Hybrid Hybridisation and Bonding
State of C

trigonal
H
Benzene sp2
CeHe planar with
respect to
wch C
atom
Symbol (molecule
for
is planar,
benzene:
flat)

1-\
\z/ Each C atom uses two of its sp2 hybrid orbitals to overlap head-on with
the spz hybrid orbital of 2 adjacent C atoms, forming a total of 6 C-C o
bonds
Each C atom uses its remaining sp? hybrid orbita,l to overlap hea$-gn
with 1s orbital of H, forming a total of 6 C-H o bonds.

d H

Each C atom has an unhybridised 2p orbital. These 6 orbitals

(perpendicular to the planar arrangement of C atoms) overlap side-wav
together, forming electron clouds above and below the plane of the
ring. These electron clouds contain a total of six delocalised n
electrons.

1O RECYCLING

10.1 Whv the Need for Recvclinq?

" . Metals are produced commercially from ores.

. Common ores are oxides, sulphides, halides, silicates, carbonates & sulphates.
. These are finite and non-renewable.
r Difficult to predict and estimate how long the reserves will last.
r Efforts must be made to conserve resources via successful recycling which is cost-effective.
10.2 lmportance of Recyclins
. Saye money.The high cost of extracting aluminium by electrolysis can make recycling worthwhile.
. Saye energy and fuels: Large amount of electricity is needed to extract aluminium and coke to extract
iron.
. Saye environment Dig up less metal ore, mine less coaland drill less oil.
. Save the reserues for future.
. Solye the problem of waste disposa/: Recycling metal or plastic articles prevents them from becoming
litter.

t However, recycling may not be always worthwhile because of the cost of sorting, collecting and
processing th6 waite material. The higher the value of the material, the more economical it is to recycle.
Thus, almost all gold is recycled, but only 40% of aluminium is recycled.

* Recycling plastics presents a particular problem because of the difficulty in identifying the type of polymer
used. lt ii easy to separate iron from copper in recycling but PVC and polyethene are much more difficult
to distinguish bnd separate. One way to get round this is to indicate the type of polymer by means of a
specialsymbol.

JJC 2008 Page 4O ol 42

 Comparing thefour crasses of substances
Metals lonic compounds Govalent Compounds

Type of structure Giant metallic Giant ionic Giant covalent Simple covalent
(or giant molecular) (or simple molecular)

Bonding Strong Strong electrostatic Strong covalent Strong covalent bonds

electrostatic attraction between bonds between hold atoms together
attraction between cations and anions atoms within the separate
metal cations and molecules.
the surrounding Separate molecules
mobile electrons are held by weak
intermolecular forces.

Properties
(i) Melting point, High mp and bp High mp and bp High mp and bp Low mp and bp
boiling point
(ii) Hardness Hard, yet Hard and brittle Hard Soft
malleable (except graphite)
(iii) Electrical Conduct in the Does not conduct Does not conduct in Does not conduct in
Conductivity solid or liquid in the solid state; all states all states
(molten) state Conduct in the Graphite is the
liquid or aqueous exception
state.
(iv) Solubility lnsoluble in polar Soluble in polar lnsoluble in all Less solublefinsoluble
and non-polar" solvents (eg. HzO); solvents in polar solvents;
solvents, but lnsoluble in (More) soluble in
soluble in liquid non-polar solvents non-polar solvents
metals (eg. (es. CCL)
forming alloys)

2. Solubility in Water

A compound with simple covalent structure is expected to dissolve in water if

(a) it is capable of forming hydrogen bonding with water molecules; or/and
(b) it is able to form ions which can be solvated by water molecules through the formation
of ion-diPole interaction.

An ionic compound will dissolve in water if the hydration energy released from the iondipole
interaction is zumcient,to overcome the strong ionic bonds in the ionic compound"

Exercise 14: Explain the following observations in terms of the structure and bonding of the substances'
(a) SiOz is a solid whereas CO2 is a gas at room temperature.
iOl Hyd?ogen chloride has a higher b;iling point than fluorine even though their M are similar.
I \ilr- / 'lqq-:ctrUCture.
(a) SiO2 has g ,,i('iir,\ "-i {':'*---o.'t*itructure. COz has a -iivr,'l'\r
Larger amount of energy is needed to overcoms tlg f ii'l':, I " ''i:i'- L' t ' i between
in SiOz than the -'"q"r'i 'r' 4ir.'t '-:;i{:'f\Ii "rtl'''')
r..1 .d.\, i L^!.,^^^
between
t^\

and exist as a gas at room temperature.

(b) Both HC/ and F2 have -f ii''"br'': i'*;{ i{'''"'-i r'v structure. HC/ is [- but Fz is

. --fTlt
I

r. ,
\ ,l { 1

. Larger amount of energy is needed to, overcpme the

_ , ... than the ,l\. ' "1! lt '':"-
. Therefore, HC/ has a higher b.p. than F2 even though their M. are similar'

JJC 2008 Page 41 ol 42

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