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H2 CHEMISTRY 9729
Explain why the bond energies of the halogens decreases down the group but the
reverse was observed for the boiling points
o (Concept from lecture notes page 2 – 5)
o The size of the valence orbital of the atoms / size of the atoms increases
down the group from Cl to Br to I
o Hence and this result in a less effective overlap between the orbitals from
Cl2 to Br2 to I2 (as the electron cloud in the valence orbital is more diffused)
Hence, the covalent bond formed between the atom is weaker and has
lower bond energy.
o Cl2 ,Br2 and I2 have simple molecular structures and are non-polar
o Weak instantaneous dipole – induced dipole interactions exist between
the molecules
o [Note: During the boiling process, energy is absorbed to overcome the
intermolecular forces of attraction between the molecules and not the
intramolecular covalent bonds between the atoms.]
o Down the group, the size and polarisability of the electron cloud increases from
Cl2 to Br2 to I2.
o More energy is required to overcome the stronger intermolecular
instantaneous dipole- induced dipole interactions from Cl2 to I2
o Hence boiling point increases down the group.
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 / Teacher’s copy Page 1 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
2. Explain why oxygen is a gas at room temperature whereas sulfur is a solid melting at
130 C.
o (Concept from lecture notes page 5)
o Both oxygen and sulfur have simple molecular structures and are non-polar.
o S8 molecules has a larger electron cloud which is more polarisable than O2
molecules
o More energy is required to overcome the stronger instantaneous dipole – induced
dipole between its molecules. Hence the boiling point / melting point of sulfur is much
higher than that of oxygen.
o Since the boiling point of oxygen is way below room temperature, oxygen a gas at room
temperature; and since the melting point of sulfur is 130C (much higher than room
temperature), it exist as a solid at room temperature.
(Note: Sulfur in the solid state ordinarily exists as cyclic crown-shaped S8
molecules. Sulfur has many allotropes besides S8. Removing one atom from the crown
gives S7, which is responsible for sulfur's distinctive yellow color. Many other rings have
been prepared, including S12 and S18. )
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 2 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
4. Explain why iodine solid is insoluble in water but dissolves in benzene, C6H6.
o (Concept from lecture notes page 19 – 20)
o I2 , C6H6 and H2O have simple molecular structures
o I2 and C6H6 are non-polar.
o Instantaneous dipole – induced dipole interactions exist between I2
molecules and between C6H6 molecules.
o H2O molecules are polar and are able to form hydrogen bonds between its
molecules.
o I2 dissolves in benzene C6H6 because the energy released in forming
instantaneous-dipole – induced dipole interactions between I2 and C6H6
molecules are sufficient to overcome the instantaneous dipole – induced
dipole interactions between I2 and between C6H6 molecules.
o I2 do not dissolves in water as the energy released in forming instantaneous
dipole – induced dipole interactions between I2 and H2O molecules are
insufficient to overcome the hydrogen bonds between H2O molecules and
instantaneous dipole – induced dipole interactions between I2 molecules.
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 3 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
7. The bond energy data and boiling points of the group halogen halides are given below.
bond energy boiling point
HX
(kJ mol1) (C)
HCl 431 85
HBr 366 66
HI 297 34
(a) Compare the trend in bond energy and boiling point of the halogen halides.
(b) Account for the trend in boiling point of the halogen halides.
(a)
o The bond energy decreases from HCl to HBr to HI whereas the boiling point
increases from HCl to HBr to HI.
(b)
o (Concept from lecture notes page 5,6,10)
o HCl, HBr,HI have simple molecular structures and are polar molecules
o Permanent dipole – permanent dipole interactions as well as
instantaneous dipole – induced dipole interactions exist between the
molecules
o The boiling point increases from HCl to HBr to HI as the size and polarisability
of the electron cloud increases from HCl to HBr to HI.
o More energy is required to overcome the stronger intermolecular
instantaneous dipole- induced dipole interactions from HCl to HBr to HI.
o Hence, boiling point increases down the group.
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 4 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
Draw a diagram to show how hydrogen bonding occurs between two molecules of
ethane-1,2-diol.
(Concept from lecture notes page 11)
Hydrogen bond
- +
||||||||||||||
..
+
-
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 5 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
10. Explain why the boiling point of H2O (100 oC) > HF (19.5 oC) > NH3 (−33.5 oC).
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 6 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
O: H O
CH3CH2 C C CH2CH3
O H :O
Hydrogen bond
o Hence the Mr that was measured is double that of a molecule of propanoic acid (Mr =
74.0)
o When dissolved in water, propanoic acid forms hydrogen bonds extensively with
water molecules, and is therefore unable to form dimers.
12. N09/P3/4b
The molecules of ammonia and methane contain the same number of electrons, and have
approximately the same size and mass. Their boiling points differ widely, however.
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 7 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
boiling point
name formula Mr
(C)
pentane C5H12 72 36
butan-1-ol C4H9OH 74 117
propanoic acid C2H5CO2H 74 141
1-aminobutane C4H9NH2 73 78
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 8 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
o In propanoic acid, the presence of another electronegative oxygen atom causes the
+ charge on the H atom directly bonded to the O atom in propanoic acid to be
greater than the + charge on the H atom directly bonded to the O atom in butan-
1-ol.
14. Explain why the boiling points of water (H2O), ethanol (CH3CH2OH) and ethoxyethane
(C2H5OC2H5) are in the reverse order of their molecular masses, unlike those of their
analogous sulfur compounds: H2S, C2H5SH and C2H5SC2H5.
o Both water, ethanol and ethoxyethane are have simple molecular structures and are
polar
o Intermolecular hydrogen bonds exists between water molecules and between
ethanol molecules, whereas only permanent dipole – permanent dipole interactions
exist between ethoxyethane molecules.
o More energy is thus required to overcome the much stronger hydrogen bonds in water
and ethanol, than the permanent dipole – permanent dipole interactions in
ethoxyethane.(even though the instantaneous dipole – induced dipole interactions in
ethoxyethane is the strongest of the 3 compounds due to its largest molecular size.)
o Hence, the boiling point of ethoxyethane is the lowest.
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 9 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
o The hydrogen bonding between water molecules is more extensive than that
formed between ethanol molecules.
o Hence more energy is required to overcome the more extensive hydrogen
bonding between water molecules than that between ethanol, and hence water
has a higher boiling point than ethanol.
o For the sulfur compounds, the trend of boiling point is expected to be: H2S < C2H5SH <
C2H5SC2H5
o H2S ,C2H5SH ,C2H5SC2H5 have simple molecular structures and are polar (Note: The
order of the boiling points is the same as the order of the molecular masses. All three
compounds are polar molecules but are not capable of forming hydrogen bonds,instead
permanent dipole – permanent dipole interaction and instantaneous dipole – induced
dipole interactions exists between the molecules. Difference in boiling point is due to
the difference in strength of the instantaneous dipole – induced dipole interaction since
the Mr and hence size of the electron cloud of each compounds is significantly
different. )
o The Mr of : H2S < C2H5SH < C2H5SC2H5
o C2H5SC2H5 has the largest Mr and hence a larger more polarisable electron than
C2H5SH and H2S.
o Hence, more energy is thus required to overcome the stronger instantaneous dipole
– induced dipole interactions between C2H5SC2H5 molecules than that between
C2H5SH molecules and H2S molecules.
15. DHS/2011/P2/Q4(a),(b)
Group 14 elements progress towards metallic behaviour down the group. The table
below shows selected data for the dioxides from carbon to germanium.
melting point
compound formula
(°C)
carbon dioxide CO2 78
silicon dioxide SiO2 1600
germanium dioxide GeO2 1200
a) State the valence shell electronic configuration of these elements (group 14) ,
and their oxidation state in the above dioxides.
b) Explain in terms of structure and bonding, the difference in melting points
between carbon dioxide and silicon dioxide, with respect to bonding and
structure.
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 10 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 11 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
16. N07/P3/Q4b(i)
The melting point of beryllium nitrate, Be(NO3)2, is 60 °C, whereas that of calcium
nitrate is 561 °C. Use these data to suggest the nature of the bonding in beryllium
nitrate and in calcium nitrate, explaining your answer.
o Be(NO3)2 has a simple molecular structure since it has a low melting point.
o Ca(NO3)2 has a giant ionic lattice structure since it has a high melting point.
o Hence, lesser amount of energy is required to overcome the instantaneous-
dipole induced dipole between the non-polar Be(NO3)2 molecules whereas a
larger amount of energy is required to overcome the stronger electrostatic
forces of attraction between Ca2+ and NO3− ions.
17. N12/P3/Q4c(ii)
Na, Si, P and Cl differ greatly in their melting points.
Describe how their melting points differ and explain this variation
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 12 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 13 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
boiling point
compound Mr
(C)
methanoic acid, HCOOH 46.0 100
ethanol, CH3CH2OH 46.0 78
ethylamine, CH3CH2NH2 45.0 17
o HCOOH, CH3CH2OH and CH3CH2NH2 have simple molecular structures. They are
polar and are capable of forming hydrogen bonds between their molecules.
o HCOOH has the highest boiling point. As the dipole moment of the H−O bond in
methanoic acid, HCOOH, is largest of the three organic compound due to the two
highly electronegative O atoms. Thus more energy is required to overcome the
hydrogen bonding in methanoic acid than in the other two compounds.
o As the dipole moment of the H−O bond is larger than that of the H−N bond (as O is
more electronegative than N), the hydrogen bonds formed between ethanol
molecules are stronger than those between ethylamine molecules. Hence more
energy is required to overcome the hydrogen bonding in ethanol than in ethylamine.
Hence boiling point: methanoic acid > ethanol > ethylamine
20. Arrange the following compounds, CH3CH2CH3, CH3CH2OH, and CH3COCH3, in order
of increasing boiling point and explain your reasoning.
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 14 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 15 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
22. VJC/2010/P2/Q4(b)
Sulfur dichloride oxide (thionyl chloride), SOCl2, is a useful reagent in organic
synthesis, converting −OH groups into −Cl groups.
R−OH + SOCl2 RCl + HCl + SO2
(i) Draw a dot-and-cross diagram of SOCl2.
(ii) Suggest the size of the bond angle around the sulfur atom in SOCl2.
(iii) Methanol, CH3OH, and thionyl chloride, SOCl2, differ in their boiling points
boiling point
compound
(C)
CH3OH 65
SOCl2 75
Account for the difference in the boiling point of these two compounds in terms of
relevant intermolecular forces.
(i)
(ii)
o (Not required according to the phrasing of the question: As there are 3 bond pairs and
1 lone pairs of electrons around the central sulfur atom, to minimise the repulsion, the
electron pairs will space themselves out as far apart as possible, and the electronic
geometry would be tetrahedral. However, as the lone pair − bond pair repulsion is
stronger than bond pair – bond pair repulsion, the bond angle would be smaller than
the standard angle of a regular tetrahedron - 109)
o 107
(iii)
o CH3OH and SOCl2 have simple molecular structures and are polar.
o Hydrogen bonds exist between CH3OH molecules, while permanent dipole –
permanent dipole interactions exist between SOCl2 molecules.
o (Note: Hydrogen bond are stronger than permanent dipole – permanent dipole
interactions if the size of the electron cloud of both molecules are similar. i.e. similar Mr.
In this question, Difference in boiling point is due to the difference in strength of the
instantaneous dipole – induced dipole interaction since the Mr and hence size of the
electron cloud of each compounds is significantly different. )
o SOCl2 contains significantly more electrons and hence have a significantly
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 16 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
larger, more polarisable electron cloud than CH3OH (as seen from the Mr: CH3OH –
32.0; SOCl2 – 118.1). Hence, more energy is required to overcome the stronger
instantaneous dipole – induced dipole interactions between SOCl2 molecules
than the hydrogen bonding between CH3OH molecules.
23. PJC/2010/P3/Q5(a),(b)
(a) Hydrazine, N2H4, has an ammonia-like odour and is derived from the same
industrial chemical processes that manufacture ammonia. In some cases
hydrazine behaves like ammonia in chemical reactions. For example, hydrazine
is able to form a product when it reacts with boron trifluoride, BF3, in a mole ratio
of 1 : 1.
(i) Draw the ‘dot-and-cross’ diagram of a molecule of N2H4. Use the electron pair
repulsion theory to predict the shape and state the H-N-H bond angle of this
molecule.
(ii) Draw a diagram to show the shape of the product formed when hydrazine
reacts with BF3, in a mole ratio of 1 : 1.
(b) Ethene, C2H4, and hydrazine, N2H4, are hydrides of elements which are adjacent
in the Periodic Table.
The boiling point of hydrazine is much higher than that of ethane. Account for this
difference in terms of their structure and bonding.
(a)(i)
As there are 3 bond pairs and 1 lone pairs of electrons around the central nitrogen atom, to
minimise the repulsion, the electron pairs will space themselves out as far apart as
possible, and hence the shape of the molecule (around each central N atom) is trigonal
pyramidal.
(Not required according to the phrasing of the question: As the lone pair − bond pair
repulsion is stronger than bond pair – bond pair repulsion, the bond angle would be smaller
than the standard angle of a regular tetrahedron - 109)
107
(ii)
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 17 of 18
JC1 Chemistry Tutorial 6: Intermolecular Forces YISHUN JUNIOR COLLEGE
(b)
o C2H4 and N2H4 have simple molecular structures.
o C2H4 is non-polar while N2H4 is polar.
o Instantaneous dipole – induced dipole interactions exist between C2H4
molecules, while hydrogen bonds exist between the polar N2H4 molecules.
o (Note: the strength of the instantaneous dipole – induced dipole interaction in the two
compounds are similar, as both compounds have similar Mr)
o More energy is required to overcome the stronger hydrogen bonding that exist
between N2H4 molecules than the weaker instantaneous dipole – induced dipole
interactions between C2H4 molecules
24. Radioactive CsCl has high a rather high toxicity to humans and animals due to the
137
radioactive caesium ion. Spread of solid CsCl powder from a 93-gram container in
1987 in Goiania, Brazil, resulted in one of the worst-ever radiation spill accidents killing
four and directly affecting more than 100,000 people who consumed the contaminated
water. Describe the structure and bonding of CsCl and draw a simple labelled diagram
to explain why aqueous caesium ions are found in the water.
Solid CsCl has a giant ionic lattice structure with strong electrostatic forces of
attraction between the oppositely charged Cs+ and Cl- ions.
In water
|||||||
Cs+
|||||||
||||||| |||||||
|||||||
|
||||||||
||||||||
|||||||
Ion – dipole
interaction
“Ninety-nine percent of failures come from people who have the habit of making excuses.” George Washington Carver
Jacqueline Lim / YJC / 2016 /solutions Page 18 of 18