2014 chem bonding tut (students)

Nanyang Junior College H2/H1 Chemistry JC1 2014

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Chemical Bonding Tutorial

Section A: Review Questions

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1 Which of the following statements explains why copper conducts electricity when a

potential difference is applied?

A Copper(II) ions move to the cathode

B The crystal lattice breaks down

C Electrons combine with copper(II) ions

D Bonding electrons in the crystal lattice move

2 Which bonding type does not correspond to its description of physical properties?

Bonding type Physical properties

A Giant covalent High melting point, conducts electricity when in solution but not

when solid

B Simple covalent Low melting point, does not conduct electricity in any state

C Metallic Variety of melting points, conducts electricity when solid and

when molten

D Ionic High melting point, conducts electricity when molten but not

when solid

3 The C2H2 molecule is linear.

What can be deduced from this about the numbers of and pi bonds present in the

molecule?

pi

A 2 2

B 2 3

C 3 1

D 3 2

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4 Why is the molecule of BCl3 planar, whereas the molecule of PH3 is pyramidal?

A The boron atom has no d-orbitals available for bonding.

B The boron atom in BCl3 has 6 electrons in its valence shell, while the phosphorous

atom in PH3 has 8.

C The repulsion between chlorine atoms is greater than that between hydrogen atoms.

D The covalent radius of phosphorus is greater than that of boron.

5 MBTE is a constituent of petrol.

What are the values of angle P and angle Q in a molecule of MTBE?

Angle P Angle Q

A 90 105

B 90 180

C 109 105

D 109 180

6 AlCl3 reacts with LiAlH4 and (CH3)3N to give (CH3)3NAlH3.

Which statement about (CH3)3NAlH3 is correct?

A It contains hydrogen bonding

B It is dimeric

C The Al atom is electron deficient

D The shape about the Al atom is tetrahedral

7 Why is the boiling point of methane greater than that of neon? [Ar: H, 1; C, 12; Ne, 20]

A A molecule of methane has a greater mass than a molecule of neon.

B A molecule of methane has more electrons than a molecule of neon.

C Molecules of methane have stronger intermolecular forces than those of neon.

D Molecules of methane form hydrogen bonds, but those of neon do not.

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8 Which of the following solids consists of atoms or molecules held together only by van der

Waals forces?

A CO2

B Cu

C H2O

D MgO

9 Which of the following molecules will not form a hydrogen bond with another of its own

molecules?

A CH3CHO

B CH3NH2

C CH3OH

D NH3

10 When heated, solid iodine readily forms iodine vapour.

What does this information suggest about the nature of the particles in these 2 physical

states of iodine?

Solid Vapour

A ionic atomic

B ionic molecular

C molecular atomic

D molecular molecular

11 Which set of properties could apply to a non-ionic compound which has a giant lattice?

Physical state at room

temperature

Electrical conductivity in

molten state

Melting point / C

A liquid Does not conduct -114

B liquid Does not conduct Melts over a range

C solid Conducts well 808

D solid Does not conduct 1610

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The responses A to D should be selected on the basis of

A B C D

1, 2 and 3

are correct

1 and 2

only are correct

2 and 3

only are correct

1 only

is correct

No other combination of statements is used as a correct response.

12 Which of the following are features of the structure in metallic copper?

1 Ionic bonds

2 Delocalised electrons

3 Lattice of ions

13 In microwave ovens, the wave energy produced is absorbed by certain polar molecules.

Which of the following would absorb microwave energy?

1 C2H5OH

2 NaCl

3 SiO2

14 The boiling points of pentane and 2,2-dimethylpropane are 36 C and 9 C respectively.

Which of the following suggested factors help to account for this difference in boiling

points?

Pentane 2,2-dimethylpropane

1 The molecule of 2,2-dimethylpropane is more compact than that of pentane.

2 The covalent bonds in pentane are stronger than those in 2,2-dimethylpropane.

3 There is more effective hydrogen bonding in pentane than in 2,2-dimethylpropane.

15 Many ceramic materials based on silicon(IV) oxide have recently been developed. Which

properties apply to these materials?

1 They are heated during manufacture and form solids.

2 They are heat-resistant solids.

3 They are good conductors of electricity due to delocalised electrons.


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16 a) Explain what is meant by sigma () and pi (pi) bonds. Illustrate your answers with

suitable diagrams.

Refer to lecture notes Page 13 and 14.

b) How many sigma () and pi (pi) bonds are present in the propene (C3H6) molecule?

8, 1pi

17 For the following particles,

draw their dot-and-cross diagrams

count the total number of lone pairs and bond pairs

state their shapes according to VSEPR theory

draw their shapes

give the bond angles about the central atom

state whether they are polar or non polar (only applicable for molecules)

Particle Dot-and-cross diagram / Structure

Bond pairs

/ Lone

pairs

Shape, Bond

Angle, Polarity

NF3

!

3 bp

1 lp

Trigonal

pyramidal 107

SiF4

!

4 bp

0 lp

tetrahedral

109

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Bond pairs

/ Lone

pairs

Shape, Bond

Angle, Polarity

CH2Cl2

!

4 bp

0 lp

tetrahedral

109

ICl3

!

3 bp

2lp

T shape

90

ClO

NH2

2 bp

2 lp

Bent

105

H3O+

3 bp

1 lp

Trigonal

pyramidal

107

NO3

3 bp

0 lp

Trigonal planar

120

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Bond pairs

/ Lone

pairs

Shape, Bond

Angle, Polarity

AlH4

4 bp

0 lp

tetrahedral

109

BrCl2

2 bp

3 lp

Linear

180

I3

2 bp

3 lp

Linear

180

SO42

!

4 bp

0 lp

tetrahedral

109

18 a) Describe the bonding present in

(i) solid krypton, 36Kr,

Solid krypton exists as a lattice of atoms with weak van der Waals forces between Kr

atoms.

(ii) solid rubidium, 37Rb.

Rubidium has a giant metallic lattice with strong metallic bonds between the cations

and the sea of delocalised electrons.

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b) Use your descriptions of their bonding to explain why the boiling point of krypton is

152C whereas that of rubidium is 686C, despite their having nearly the same

relative atomic mass, Ar.

More energy is required to overcome the stronger

metallic bonds in Rb than the weak van der Waals

forces in Kr. Hence Rb has a higher b.p. than Kr.

19 The table below gives the boiling points of four organic compounds:

formula relative molecular mass boiling point /oC

A CH3CH2CH2CH2CH3 72 36

B (CH3)4C 72 10

C CH3CH2CH2CH2OH 74 117

D CH3CH2OCH2CH3 74 35

By comparing i) A with B, ii) A with C and iii) C with D, suggest explanations for the

differences in the boiling points within each of the three pairs.

i) A with B

Both A and B have simple molecular structure with weak

van der Waals forces between molecules.

A has a straight chain structure while B has a more

spherical shape due to its highly branched structure.

The vdW forces between A molecules are stronger than that of B due to the large

surface area of contact. More energy is required to overcome the stronger vdW forces,

higher bp.

ii) A with C

Both A and C have simple molecular structure. There are weak van der Waals forces

between A molecules, and H-bonds between C molecules.

More energy is required to overcome the stronger H-bonds than vdW forces, so C has

a higher bp.

iii) C with D

Both C and D have simple molecular structure. There are H-bonds between C

molecules and pd-pd interactions between D molecules.

More energy is required to overcome the stronger H-bonds than pd-pd interactions, so

C has a higher bp.

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20 Explain the following observations in terms of the structure and bonding present.

a) 4-hydroxybenzoic acid is more soluble in water than 2-hydroxybenzoic acid.

OH

O OH

4-hydroxybenzoic acid

O OH

OH

2-hydroxybenzoic acid

!

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In 2-hydroxybenzoic acid, COOH and OH

groups are close to each other.

They can form intramolecular H-bonds

This reduces the chance of forming H-bonds

with water molecules.

Hence it is less soluble in water

b) In benzene solution, the measured relative molecular mass of methanoic acid is

approximately 92.0. Explain the observation and include a relevant diagram in your

answer.

In benzene solution, methanoic acid dimerises through

hydrogen bonds.

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Section B: Discussion Questions

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1 In which of the following pairs does the first substance have a higher melting point than the

second?

First Second

A CH3CH2OCH3 CH3CH2NHCH3

B (CH3)3CH CH3CH2CH2CH3

C RbCl KCl

D

2 The concepts of bond energy, bond length and bond polarity are useful when comparing

the behaviour of similar molecules.

Compared with the HCl molecule, the bond __X__ of the HI molecule is __Y__.

Which pairs of words correctly complete the above sentence?

X Y

1 energy greater

2 length greater

3 polarity less

3 In which of the following reactions is the bond angle in the product greater than that in the

reactant?

1 H2O (l) + H+ (aq) ! H3O

+ (aq)

2 C2H4 (g) + H2 (g) ! C2H6 (g)

3 CO2 (g) + OH- (aq) ! HCO3

- (aq)

C

O

OH

OHC

O

OH

OH


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4 Carbon forms double bonds with each of the Group VI elements oxygen, sulfur and

selenium. In each case, the double bond is polar.

In the molecules CO2, COS and COSe, the polarities of these double bonds do not

necessarily cancel.

Overall polarity of molecule

CO2 0

COS 0.71

COSe 0.73

Which factors could account for these observations?

1 The C=S bond is more polar than the C=Se bond.

2 The C=O bond is more polar than the C=S bond.

3 The C=Se bond is more polar than the C=O bond.

5 In 1985, a molecular form of carbon, C60, called buckerministerfullerene, was discovered in

the products formed when graphite was vapourised. The structure proposed for the

molecule is a roughly spherical collection of atoms in the shape of hexagons and

pentagons, very much like a soccer ball.

Which of the following properties is expected of buckerministerfullerene?

1 It dissolves in various organic solvents.

2 It has a high melting and boiling point.

3 It can conduct electricity.

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6 When magnesium is burnt in air, a mixture of the ionic solids magnesium oxide, MgO,

and magnesium nitride, Mg3N2, is formed.

a) Explain why magnesium metal is deformed by an applied force, whereas magnesium

oxide is shattered.

Mg has a giant metallic lattice with strong metallic

bonds between cations and the sea of delocalised electrons. MgO has a giant ionic

lattice of cations and anions with strong ionic bonds between ions.

When a force is applied to Mg, the cation layers slide past one another, but the sea

of delocalised electrons move to prevent repulsion between the cations. Hence, the

metal is deformed.

When a force is applied to MgO, the lattice is displaced slightly and the ions with

similar charge come together and repel. Hence, the lattice breaks apart and shatters.

b) Use a dot-and-cross diagram to describe the bonding in Mg3N2.

c) State the factors that affect the magnitude of the lattice energy of an ionic

compound.

!

q qLattice energy | |

r r

+

+ +!

(proportional to product of the ionic charge and inversely proportional to the sum of

the ionic radii)!

q+ and q- represent the charges on the cation and anion, and r+ and r- the ionic

radius of the cation and anion.

d) How would you expect the magnitudes of the lattice energies of the oxides of the

Group!II elements to vary down the group?

Down group II, the ionic radius of the group II cations increases due to increasing

number of filled electron shells.

The sum of the ionic radii increases and the magnitude of the lattice energy

decreases.

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e) Suggest how the magnitude of the lattice energy of Mg3N2 might compare to that of

MgO. Explain your answer.

The magnitude of the lattice energy will increase as N3- is triply charged and the

product of the ionic charge will increase. (Charge is a more important factor than

ionic radius.)

7 Antimony, Sb, is in Group V of the Periodic Table. It forms a series of salts which contain

the SbF5n anion, the structure of which is a square-based pyramid.

Deduce the total number of electrons around the antimony atom, the value of n and the

oxidation number of Sb in this ion. [2]

Total number of electrons around Sb = 12.

(1 lone pair and 5 bond pairs ard Sb since the shape is square pyramidal.)

n = 2, Oxidation number of Sb = +3

8 Hydrogen cyanide, HCN, is a weak acid that is extremely poisonous and volatile. A

hydrogen cyanide concentration of 300 mg/m3 in air will kill a human within 1060 minutes.

a) Draw the dot and cross diagram for HCN and predict its shape.

linear about C

b) Draw the structural formula of the cyanide anion formed upon dissociation of HCN in

water. Do you notice anything unusual about it?

The negative charge is on the less electronegative C.

(Explain that the cyanide ion is a special case.)

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Page 14 of 18

c) Explain why HCN is so volatile.

HCN has a simple molecular structure with pd-pd interactions between molecules.

These interactions are weak and require little energy to overcome, so low bp, high

volatility.

d) HCN, N2 and CO are isoelectronic. The bond energy of the nitrogen-nitrogen bond in

the nitrogen molecule is 944kJ mol1, whereas the bond energy of the carbon-oxygen

bond in the carbon monoxide molecule is 1074 kJ mol1. Explain this observation.

The NN bond is non polar but the CO bond is polar.

There is extra attraction due to partial charges in the

bond.

9 a) Draw structures and state the bond angles for the following particles.

(i) NO2+ (ii) NO3

(iii) N2O5

180 120 120 about N and 105 about O

b) NO2 has a bond angle of 134 and NO2 has a bond angle of 115, although VSEPR

theory predicts that both bond angles should be 120.

Explain.

(Both 2 bp, 1 lp.)

When there are have 3 electron pairs around the central atom, the shape should be

trigonal planar, bond angle 1200.

For NO2-, lp lp repulsion is greater than that of bp bp repulsion. The bond pairs are

forced to go closer to each other, causing the angle to be smaller than 120o.

There is only 1 lone electron on N in NO2 (instead of a lp). 1 lone electron will not exert

as large a repulsion on the bond pairs as compared to a bond pair. Hence, the angle is

smaller than 120o.

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Page 15 of 18

10 It is known that AlCl3 and NH3 react readily.

a) Draw the dot-and-cross diagram of the product of this reaction. Predict the likely shape

of the product.

tetrahedral about Al and N

b) Explain why these two molecules form a product when they react in a molar ratio of

1:1.

NH3 has a lone pair available for donation. AlCl3 is electron deficient and has an

empty, energetically accessible orbital to accept electrons.

c) Similar products may be obtained when the following compounds are reacted together.

Suggest the structures and shapes of their products.

(i) BeC!2 and NH3

tetrahedral about Be and N

(ii) BF3 and NaF

tetrahedral about B

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11 In 1886, Henri Moissan succeeded in obtaining fluorine by the electrolysis of molten

potassium difluoride, KHF2, which is an ionic compound containing one cation and one

anion.

a) Write the formulae of the ions present in KHF2.

K+, HF2

b) Suggest a structure for the anion and state what types of bonding occur within it.

c) Explain why KHF2 has a melting point of 239 C, but that of KF and HF are 858 C and

84 C respectively.

KHF2 and KF have giant ionic lattice structure with strong ionic bonds between ions.

HF has a simple molecular structure with hydrogen bonds between molecules.

A lot more energy is required to overcome strong ionic bonds compared to hydrogen

bonds. So HF has the lowest boiling point.

The ionic bond between K+ and F- is stronger than that between K+ and HF2- as the

size of the HF2 ion is larger. More energy is required to overcome, higher boiling

point.

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Section C: Assignment (15 marks)

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1 Nitrate, NO3-, and phosphate, PO4

3-, are oxoanions of nitrogen and phosphorus

respectively.

a) Draw dot-and-cross diagrams to show the bonding in NO3- and PO4

3-. Hence, deduce

the shapes and state the bond angles around the nitrogen and phosphorus atom. [4]

![1] [1]

Trigonal planar, 120 [1] Tetrahedral, 109 [1]

b) Explain why it is not possible for nitrogen to form an oxoanion with a formula of NO43-.

[1]

Nitrogen has no empty and energetically accessible 3d orbitals to expand its octet.

2 This question is on the properties of halogens and their compounds.

a) Halogens like Cl2 and I2 are soluble in the non-polar solvent CCl4. However, the

interhalogen compound, ICl, is insoluble in CCl4. Explain why. [2]

Cl2 and I2 are soluble in CCl4 as they can form van der Waals interactions with CCl4.

[1]

ICl is insoluble in CCl4 as the energy released during the formation of vdW interactions

with ICl is not enough to overcome the permanent dipole permanent dipole

interactions between ICl molecules (and vdW forces between CCl4 molecules). [1]

The hydrogen halides undergo thermal decomposition according to the following

equation.

2HX ! H2 + X2 (where X represents the halogen)

b) Why is the rate of thermal decomposition of hydrogen fluoride slower than that of

hydrogen iodide? [2]

The HF bond is shorter than the HI bond. [1] There is less degree of orbital overlap

and less energy is required to break the bond. [1]

15


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Page 18 of 18

3 Ethanoic acid, CH3COOH, is the main component of vinegar.

a) Explain, with illustrations, why ethanoic acid is soluble in water. [2]

Soluble as they can form hydrogen bonds with water [1]

Drawing showing at least 1 H-bond (with +, -, lone pairs, hash lines) [1]

b) Ethanoic acid (Mr = 60.0) is a liquid while magnesium fluoride (Mr = 62) is a solid at

r.t.p. Explain. [2]

Ethanoic acid has simple molecular structure with

hydrogen bonds between molecules.

Magnesium fluoride has giant ionic lattice with Mg2+ and

F- ions held together by strong ionic bonds. [1]

More energy is required to overcome the stronger ionic bond so MgF2 has a higher

melting point and is a solid at rtp, while ethanoic acid is a liquid. [1]

c) Ethanoic acid undergoes neutralisation with sodium hydroxide to form sodium

ethanoate.

CH3COOH + NaOH ! CH3COO-Na+ + H2O

Is sodium ethanoate soluble in water? Draw a diagram to explain. [2]

Soluble. Sodium ethanoate dissociates into its ions in water. These ions can form ion-

dipole interactions with water. [1]

[1]

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2014 chem bonding tut (students)

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