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(a)
hydrogen bond
[2]
(b)
hydrogen bonds
[2]
(c) Propanoic acid has a higher boiling point than propan-1-ol. [1] Propanoic acid contains the
carboxyl group,
. [1] Both
and OH groups can participate in hydrogen
bond formation. [1] As a result, it has more extensive intermolecular hydrogen bonds than
propan-1-ol. [1] More energy is needed to separate its molecules during the boiling process. [1]
(d)
[1]
Propyl propanoate [1]
2
(a)
butane [1]
butan-1-ol [1]
2-methylpropane [1]
(b) Butane and 2-methylpropane [1]
(c) 2-methylpropane < Butane < Butan-1-ol < Butanoic acid [1]
Molecules of butanoic acid and butan-1-ol are held together by hydrogen bonds as well as van der
Waals forces. [1] However, butanoic acid has more extensive intermolecular hydrogen bonds than
butan-1-ol because both C=O group and OH group can participate in hydrogen bond formation.
[1] Therefore, more energy is needed to overcome the extensive intermolecular hydrogen bonds
among butanoic acid molecules than that among butan-1-ol molecules. [1] The molecules of
butane and 2-methylpropane are held together by weak dispersion forces only. [1] Since the
strength of hydrogen bonds > dispersion forces, the boiling point of butan-1-ol is higher than that
of butane and 2-methylpropane. [1] 2-methylpropane is a branched-chain alkane which has a
smaller surface area than butane. [1] The dispersion forces between 2-methylpropane molecules
are weaker. [1] Therefore, 2-methylpropane has a lower boiling point than butane.
4
Dimethylamine [1]
Trimethylamine [1]
(c)
hydrogen bonds
[2]
(d)
hydrogen bonds
[2]
[1]
(c) Yes, it is. Because it is made by the reaction of butanoic acid, which is a carboxylic acid. [2]
(d)
water out
water in
pear-shaped flask
a mixture of ethanol, butanoic
acid and conc. H 2 SO 4
anti-bumping granule
heat
Correct set-up [1]
(a) (i)
(ii)
(iii)
(iv)
(b)
[1] or
[1]
(a)
Hex-2-ene [1]
Hexan-3-ol [1]
Hexanal [1]
Hexan-2-amine [1]
(b) Hexan-3-ol, hexanal and hexan-2-amine are soluble in water because they can form hydrogen
bonds with water molecules. [2]
(c) The increasing order of boiling point:
Hex-2-ene < Hexanal < Hexan-2-amine < Hexan-3-ol [1]
The molecules of hexan-2-amine and hexan-3-ol are held together by hydrogen bonds as well as
van der Waals forces while the molecules of hex-2-ene and hexanal are held together by van der
Waals forces only. [2] Therefore, the boiling points of hexan-2-amine and hexan-3-ol are higher
than those of hex-2-ene and hexanal. The molecules of hexanal are held together by dipole-dipole
forces as well as dispersion forces while the molecules of hex-2-ene are held together by
dispersion forces only. [2] Therefore, the boiling point of hexanal is higher than that of hex-2-ene.
Both hexan-2-amine and hexan-3-ol have hydrogen bonds among their molecules. However, the
nitrogen atom on hexan-2-amine is not as electronegative as the oxygen atom on hexan-3-ol, so
hexan-2-amine has a lower boiling point than hexan-3-ol. [1]
9
[1]
Butanoic acid [1]
[1]
2-methylpropanoic acid [1]
10
(a) It contains OH group and CHO group. [2] (Accept ROR group as answer.)
(b) It belongs to aldehydes. [1]
(c) It is soluble in water [1] because it contains OH group and CHO group which can form
hydrogen bonds with water molecules. [1]
(d) It is used as an ingredient in perfume. [1]
12
13
(a) The organic compounds that belong to the same homologous series have the same general formula.
Each member of the same homologous series differs from the next member of the series by a
CH 2 group. [2]
(b) (i) They show a steady variation in physical properties as the number of carbon atoms increases.
[1]
(ii) They have similar chemical properties. [1]
(c) (i) Functional group:
[1]
It belongs to aldehydes. [1]
(ii) Functional group:
[1]
It belongs to ketones. [1]
(iii) Functional group:
[1]
It belongs to unsubstituted amides. [1]
14
(a)
Fluoromethane
Chloromethane
Bromomethane
Iodomethane
[4]
(a) (i) It is a primary amine because one hydrogen atom in NH 3 is replaced by one alkyl group. [2]
(ii) It is a secondary amine because two hydrogen atoms in NH 3 are replaced by two alkyl
groups. [2]
(iii) It is a tertiary amine because all hydrogen atoms in NH 3 are replaced by three alkyl groups.
[2]
(b) (i) The nitrogen atom is not as electronegative as the oxygen atom. [1]
(ii)
hydrogen bond
[2]
(c) It is because hydrogen bonds are formed between two ethanoic acid molecules to give a dimer. [1]
hydrogen bond
[2]
16
17
(a)
[1]
(b) 2-methylpropanoic acid [1]
(c)
hydrogen bonds
18
[3]
Although both compounds have hydrogen bonds between their molecules, the nitrogen atom is not
as electronegative as the oxygen atom. [1] As a result, the hydrogen bonds between CH 3 COOH
molecules are stronger than that between CH 3 (CH 2 ) 2 NH 2 , more energy is needed to overcome the
stronger hydrogen bonds among CH 3 COOH molecules during boiling. [1]
19
(a) (i)
[1]
(ii) CH 3 C(CH 3 ) 2 CH 3 [1]
(b) (i)
[1]
(ii) CH 2 =CHC(CH 3 )=CH 2 [1]
(c) (i)
[1]
(ii) CH 2 ClCBr=CH 2 [1]
(d) (i)
1]
(ii) CH 3 (CH 2 ) 2 CO 2 H [1]
(e) (i)
[1]
(ii) CH 3 COCH 3 [1]
20
(a)
[1]
[1]
3-methylbutanone
2-methylbutanoic acid
[1]
[1]
2-methylbutan-1-ol
2-methylbutanal
(a)
(b)
(c)
(d)
(e)
(f)
22
(a)
1,3-dichloropropanone [1]
2,2-dichloro-3-formylpropanoic acid [1]
2-fluorobutanedial [1]
Butyl 4-chloropent-2-enoate [1]
1,2-diaminopropane-1,3-diol [1]
Ethanedioic acid [1]
[1]
(b)
[1]
(c)
[1]
(d)
[1]
(e)
[1]
(f)
[1]
23
(a) (i)
(ii)
(iii)
(iv)
(b) (i)
[1]
(ii)
[1]
(iii)
[1]
(iv)
[1]
24
(a) (i)
[1]
(ii) CH 3 CCH 3 =CHCOCH 3 [1]
(b) (i)
[1]
(ii) CH 2 OHCH 2 CH=CHCH 3 [1]
(c) (i)
[1]
(ii) CH 3 COCOCH 3 [1]
(d) (i)
[1]
(ii) NH 2 CHOHCH 2 COCHO [1]
(e) (i)
[1]
(ii) CH 3 CH 2 CH 2 NH 2 [1]
25
CH 3 COOH [1]
CH 3 COCH 3 [1]
CH 3 CH(OH)CH 3 [1]
CHCl 3 [1]
HCHO [1]
(c) The molecules of CH 3 COOH are held together by hydrogen bonds as well as van der Waals forces
while the molecules of HCHO are held together by weak van der Waals forces only. [2] Since the
strength of hydrogen bonds > van der Waals forces, more energy is needed to break the strong
hydrogen bonds among CH 3 COOH molecules during boiling. [2]
26
(a) (i)
[1]
[1]
[1]
[1]
[1] and
[1]
(b) 2,4-dimethylpentenedioic acid exhibits both geometrical isomerism and enantiomerism. [1]
Each doubly-bonded carbon atom is attached to two different atoms or groups of atoms, so
geometrical isomers are possible. [1] Besides, it has a chiral carbon atom, so enantiomers are
possible. [1]
[1] and
[1]
[1] and
[1]
[1] and
28
[1]
geometrical isomers are possible. [1] Besides, it has a chiral carbon atom, so enantiomers are
possible. [1]
[1] and
[1]
(b) CH 3 CH=CHCHCH 3 COOH exhibits both geometrical isomerism and enantiomerism. [1]
Each doubly-bonded carbon atom is attached to two different atoms or groups of atoms, so
geometrical isomers are possible. [1] Besides, it has a chiral carbon atom, so enantiomers are
possible. [1]
[1] and
[1] and
29
[1]
[1]
(a)
[1]
(b) His statement is incorrect. [1]
Since the pair of enantiomers of mecoprop has the same intermolecular forces, they have very
similar physical properties, e.g. boiling point and melting point. [1] Therefore, it is impossible to
distinguish them by simply comparing their boiling points and melting points.
(c) His statement is partly correct. [1]
The plane of polarized light is not rotated by the mixture of the pair of enantiomers of mecoprop
only if they are present in the same amount. [1]
30
[2]
(c) The enantiomers of tartaric acid can rotate the plane of polarized light to different directions. [1]
Therefore, they can be distinguished by measuring their optical activities using a polarimeter. [1]
31
[1]
(e) Trans-glutaconic acid has a higher melting point. [1] It has a more regular and symmetrical
structure than cis-glutaconic acid. [1] Therefore, it has a higher packing efficiency in the solid
state. [1] The intermolecular forces holding the molecules together are thus stronger. [1] More
energy is needed to overcome these intermolecular forces during the melting process.
(f) Trans-glutaconic acid is more soluble in water. [1] For trans-glutaconic acid, the two carboxyl
groups are pointing to the opposite directions. Intermolecular hydrogen bondings are formed
between trans-glutaconic acid molecules and water molecules. [1]
Intermolecular hydrogen
bonds
[2]
On the contrary, for cis-glutaconic acid, due to the close proximity of the two carboxyl groups,
intramolecular hydrogen bonds can be formed readily. [1] Less intermolecular hydrogen bonds can
be formed between cis-glutaconic acid molecules and water molecules.
[2]
32
[1]
(d) The enantiomers of compound A were present in the same amount, so the optical activity of each
enantiomer was cancelled out. [2]
33
(i)
[1]
and
[1]
Trans-hex-3-ene [1]
Cis-hex-3-ene [1]
(ii)
[1] and
[1]
(c)
[1]
34
(a) The reaction should be carried out in the presence of sunlight. [1]
(b) (i)
[1]
1-bromobutane [1]
and
[1]
2-bromobutane [1]
(ii) C 4 H 9 Br exhibits position isomerism. [1] 1-bromobutane and 2-bromobutane are position
isomers. [1] Besides, it exhibits enantiomerism. [1] The C-2 carbon atom in 2-bromobutane is
attached to four different atoms or groups of atoms, so it has a chiral carbon atom in the
molecule and exhibits enantiomerism. [1]
(c)
[1] or
35
[1]
[1] and
[1]
[1] and
[1]
(c) Since the pair of enantiomers can rotate the plane of polarized light to different directions, [1] it is
possible to distinguish them by measuring their optical activities using a polarimeter. [1]
37
(a) Isomers are compounds with the same molecular formula but different arrangements of atoms in
space. [1]
(b) (i)
[1]
[1]
[1]
(ii)
[1] and
[1]
38
[1]
[1]
[1]
[1]
[1]
39
[1]
(b) The amino acid molecule exhibits enantiomerism [1] because it has a chiral carbon atom. [1]
(c)
[1] and
[1]
(d) Since the enantiomers of the amino acid can rotate the plane of polarized light to different
directions, [1] they can be distinguished by measuring their optical activities using a polarimeter.
[1]
40
(a) (i)
[2]
(ii) 3-methylpent-1-yne could exhibit enantiomerism [1] because it has a chiral carbon atom. [1]
(b) (i)
[2]
(ii) 2-methylbutanal could exhibit enantiomerism [1] because it has a chiral carbon atom. [1]
(c) (i)
[2]
(ii) 3-methylpentan-2-one could exhibit enantiomerism [1] because it has a chiral carbon atom.
[1]
41
(a) Enantiomerism occurs when there are two isomers that are mirror images of one another but are
non-superimposable. [2]
(b) The 2,4-dichloro-1,5-difluoropentan-3-one molecule has two chiral carbon atoms. [1]
(c)
[3]
(d)
[1] and
42
[1]
(a)
1-chloropropan-1-ol [1]
2-chloropropan-1-ol [1]
3-chloropropan-1-ol [1]
1-chloropropan-2-ol [1]
2-chloropropan-2-ol [1]
Referring to the above structural formulae, 1-chloropropan-1-ol, 2-chloropropan-l-ol and
1-chloropropan-2-ol could exhibit enantiomersim because they have chiral carbon atoms in their
molecules. [1]
44
(a) 3-bromobut-1-ene and but-2-enoic acid could undergo addition reactions [2] because both of them
have carbon-carbon double bonds. [1]
(b) (i) But-2-enoic acid and 1-chloropropan-1-ol [2]
(ii) CH 3 CH=CHCOOH + CH 3 CH 2 CHClOH
CH 3 CH=CHCOOCHClCH 2 CH 3 + H 2 O [1]
(c) But-2-enoic acid could exhibit geometrical isomerism. [1]
Each doubly-bonded carbon atom is attached to two different atoms or groups of atoms, so
geometrical isomers are possible. [1]
The structural formulae of the cis and trans isomers of but-2-enoic acid are shown as follows:
[1] and
[1]
[1] and
45
(a)
(b)
(c)
(d)
46
(a) (i)
[1]
Markovnikovs rule states that when a molecule of HX is added to an alkene, the hydrogen
atom is added to the carbon atom of the carbon-carbon double bond that already carries the
larger number of hydrogen atoms. [2]
(ii) The major product is 2-iodopropane [1] and the minor product is 1-iodopropane. [1]
(b) (i) Compound X is propan-2-ol. [1]
(ii) CH 3 CHICH 3 + NaOH CH 3 CH(OH)CH 3 + NaI [1]
(iii) Reagent Y is concentrated sulphuric acid. [1]
47
(a) (i)
Ethanol is mixed with acidified potassium dichromate solution and the reaction mixture is
heated under reflux gently. [2]
(ii) The reaction mixture changes from orange to green. [1]
The orange dichromate ions are reduced to green chromium(III) ions. [1]
(b) Ethanol is mixed with acidified potassium dichromate solution. [1] The reaction mixture is
warmed to a temperature that is above the boiling point of ethanal but below that of ethanol. [1]
Ethanal is distilled out as soon as it is formed, preventing it from further contact with the oxidizing
agent. [1]
48
49
(a) It was because propan-1-ol was first oxidized to propanal and it was then further oxidized to
propanoic acid. [1]
(b) The reaction mixture of propan-1-ol and acidified potassium dichromate solution was warmed to a
temperature that is above the boiling point of propanal but below that of propan-1-ol. [2] Propanal
was distilled out as soon as it was formed, avoiding any further contact with the oxidizing agent.
[1]
(c) Acidified potassium permanganate solution [1]
51
(a) Mix the two compounds with bromine solution (dissolved in an organic solvent) in darkness
respectively. [1]
Only propene could decolorize bromine solution while propane could not. [1]
(b) Mix the two compounds with acidified potassium dichromate solution respectively. [1]
Only propanal could change acidified potassium dichromate solution from orange to green while
propanone could not. [1]
(c) Mix the two compounds with acidified potassium dichromate solution respectively. [1] Then, heat
the mixture gently under reflux. [1]
Only butan-2-ol could change acidified potassium dichromate solution from orange to green while
2-methylpropan-2-ol could not. [1]
52
(a) (i)
53
55
(a)
[1] and
[1]
(a) The two compounds are heated with acidified potassium dichromate solution respectively. [1]
Butan-2-ol reacts with acidified potassium dichromate solution and changes the reaction mixture
from orange to green. [1] However, 2-methylpropan-2-ol does not react with acidified potassium
dichromate solution. It does not cause any colour change. [1]
(b) The two compounds are heated with acidified potassium dichromate solution respectively. [1]
Propanal reacts with acidified potassium dichromate solution and changes the reaction mixture
from orange to green. [1] However, propanone does not react with acidified potassium dichromate
solution. It does not cause any colour change. [1]
(c) The two compounds are mixed with sodium hydroxide solution and then followed by acidified
silver nitrate solution respectively. [2] Chloroethane gives a white precipitate [1] while
bromoethane gives a creamy precipitate. [1]
57
(c) The propan-2-ol molecules are held together by hydrogen bonds while the propanone molecules
are held together by dipole-dipole forces and dispersion forces. [2] Since the strength of hydrogen
bonds > dipole-dipole forces > dispersion forces, more energy is needed to separate propan-2-ol
molecules during the boiling process. [2]
(d) Propanone can be separated from the mixture by distillation. [1] The mixture is warmed to a
temperature that is above the boiling point of propanone but below that of propan-2-ol. [2]
58
59
(a) (i)
(ii)
(iii)
(b) (i)
(ii)
60
(a) (i)
61
(a) Compound A can react with sodium carbonate solution, so it has a COOH group. It is a
carboxylic acid. [1]
(a) Compound A was propene. [1] It reacted with bromine to form 1,2-dibromopropane which was
colourless. [1]
Compound B was propanoic acid. [1] It reacted with sodium carbonate solution to give colourless
carbon dioxide gas. [1]
Compound C was propan-1-ol. [1] It reacted with neither bromine nor sodium carbonate solution.
[1]
(b) (i) Propanoic acid [1] and propan-1-ol [1]
(ii) Concentrated sulphuric acid [1] and heating under reflux [1]
(iii) Propyl propanoate [1]
63
(a) Hydrolysis is a chemical reaction in which a compound is broken down by reaction with water. [1]
(b) (i) Sodium hydroxide solution [1]
(ii) It acts as a catalyst to speed up the hydrolysis. [1]
(c) The products are propan-1-ol and sodium methanoate. [2]
(d) It is used to make soaps. [1]
64
(a) (i) Compound A is propanoic acid and compound B is ammonium ion. [2]
(ii) Reaction 1 is an acid hydrolysis. [1]
(b) (i) Reagent C is lithium aluminium hydride in dry ether. [1]
Reagent D is dilute sulphuric acid/dilute hydrochloric acid. [1]
(ii) Reaction 2 is a reduction. [1]
65
(a) Compound A:
[1]
Compound B:
[1]
Compound C:
[1]
(b) Reaction 1 is an oxidation. [1]
Reaction 2 is an acid hydrolysis. [1]
Reaction 3 is an esterification. [1]
66
##
(a) (i) Concentrated sulphuric acid at 180C [2]
(ii) Acidified potassium dichromate solution and heating [2]
(iii) Thionyl chloride [1]
(b) (i)
[1] and
[1]
(ii)
[1]
67
[2]
[2]
[2]
(c) Hydrolysis is a chemical reaction in which a compound is broken down by reaction with water. [1]
[3]
68
[1]
(b) The two products are sodium propanoate [1] and ammonia. [1]
69
(a)
[5]
(b)
[5]
(c)
[7]
70
(a)
[7]
(b)
[7]
71
(a)
[3]
(b)
[3]
(c)
[3]
(d)
[3]
(e)
[3]
72
[6]
(b) (i) 2-chloropropane [1]
(ii)
[4]
73
(a)
[3]
(b) (i) SOCl 2 and NH 3 [2]
(ii) 2-oxopropanamide [1]
74
(ii)
[1]
and
[1]
76
(a) It is an optically active compound, so one of the carbon atoms is attached to four different atoms or
groups of atoms. [1]
The structure of compound A is
[1]
(b) (i)
(ii)
[1]
[1]
[1]
(c) (i) Oxidation [1]
(ii) Acidified potassium dichromate solution and heating under reflux [2]
(d) Compound B < Compound C < Compound A [1]
The molecules of compound A are held together by hydrogen bonds as well as van der Waals
forces. [1] The molecules of compound B are held together by dispersion forces only. [1] The
molecules of compound C are held together by dipole-dipole forces as well as dispersion forces.
[1] Since the strength of hydrogen bonds > dipole-dipole forces > dispersion forces, the boiling
point of compound A > compound C > compound B. [1]
77
(a)
[3]
(b)
[3]
(c)
[3]
78
(a) (i)
(ii)
(iii)
(b) (i)
(ii)
(iii)
79
(a)
[3]
(b)
[3]
80
(a) (i)
[1]
(ii) 2CH 3 CH 2 COOH(aq) + Na 2 CO 3 (aq) 2CH 3 CH 2 COONa(aq) + H 2 O(l) + CO 2 (g) [2]
(b) (i)
[1]
(ii) Ethanoic acid and methanol [2]
(c) (i)
[2]
(ii) 2-oxopropanoic acid [1]
81
(a)
[3]
(b)
[3]
82
(a)
[5]
(b)
[3]
(c)
[3]
83
(a) (i)
Compound A [1]
Compound B [1]
(ii) They are position isomers. [1]
(b) (i)
Compound C is propanoic acid. [1] It contains COOH group which can react with
Na 2 CO 3 (aq) to give carbon dioxide. [1]
Compound D is propanone. [1] It does not contain COOH group, so it does not react with
Na 2 CO 3 (aq). [1]
[6]
85
(a)
[3]
(b)
[3]
86
(a)
[3]
(b) Percentage yield of a product =
68.0% =
117.2 g
100% [1]
theoretical mass of the product obtained
172.4 g
(12.0 5 1.0 10 79.9 2) g mol1
60.0 g
(12.0 3 1.0 8 16.0) g mol 1
= 1 mol [1]
From the equation, the mole ratio of propan-1-ol to propene is 1 : 1,
no. of moles of propene obtained = 1 mol
Theoretical mass of propene obtained = 1 mol (12.0 3 + 1.0 6) g mol1
= 42.0 g [1]
21.0 g
100% = 50% [1]
The percentage yield of propene =
42.0 g
88
(a)
compound X [1]
aspirin [1]
(b) (i)
[2]
(ii) Esterification [1]
(iii) Compound Y is a colourless volatile liquid and immiscible with water. [2]
(c) The overall equation is
8.0 g
(12.0 7 1.0 6 16.0 3) g mol 1
(a)
[3]
(b) (i) Concentrated sulphuric acid and heating under reflux [2]
(ii) The ester is ethyl propanoate. [1]
(c) The overall percentage yield = 70% 67% 42% = 19.7% [1]
90
[2]
(c)
water out
water in
pear-shaped flask
a mixture of methanol,
propanoic acid and conc.
anti-bumping granule
heat
Correct drawing [2]
Correct labelling [1]
(d) Increase the amount of methanol. [1] Since the reaction is reversible, when there is an increase in
the concentration of methanol, the equilibrium position will shift to the product side, more
compound A can be obtained. [1]
(e) (i) Sodium carbonate reacts and removes any acidic substances, e.g. unreacted propanoic acid in
(f)
91
water in
pear-shaped flask
butan-2-ol + acidified potassium
dichromate solution
anti-bumping granule
heat
Correct drawing [2]
Correct labelling [1]
92
(a) The direction of water in and water out was reversed. [1]
There was no anti-bumping granule. [1]
The condenser should not be stoppered. [1]
(b) (i)
[2]
(ii) Propyl methanoate [1]
(c) The overall equation is
2.0 g
(12.0 1 1.0 2 16.0 2) g mol 1
= 0.0435 mol
2.5 g
= 0.0417 mol
No. of moles of propan-1-ol =
(12.0 3 1.0 8 16.0) g mol 1
From the equation, the mole ratio of methanoic acid to propan-1-ol = 1 : 1,
propan-1-ol is the limiting reagent.
From the equation, the mole ratio of propan-1-ol to propyl methanoate = 1 : 1,
no. of moles of propyl methanoate obtained = 0.0417 mol [1]
Theoretical mass of propyl methanoate obtained
= 0.0417 mol (12.0 4 + 1.0 8 + 16.0 2) g mol1
= 3.67 g [1]
2.0 g
100% = 54.5% [1]
Percentage yield of propyl methanoate =
3.67 g
93
(a) A mixture of propan-1-ol and excess acidified potassium dichromate solution is heated under
reflux for 20 to 30 minutes. [2]
(b) CH 3 CH 2 CH 2 OH + 2[O] CH 3 CH 2 COOH + H 2 O [1]
(c) Propanoic acid is separated from the product mixture by distillation. [1] Then, the distillate which
contains an aqueous solution of propanoic acid is redistilled and the fraction that boils between
140C and 142C is collected. [2]
(d) The overall equation is
3CH 3 CH 2 CH 2 OH + 2Cr 2 O 7 2 + 16H+ 3CH 3 CH 2 COOH + 4Cr3+ + 11H 2 O
The mass of propan-1-ol used = 20.0 cm3 0.8 g cm3 = 16.0 g
16.0 g
No. of moles of propan-1-ol used =
(12.0 3 1.0 8 16.0) g mol 1
= 0.267 mol [1]
From the equation, the mole ratio of propan-1-ol to propanoic acid is 1 : 1,
no. of moles of propanoic acid obtained = 0.267 mol
Theoretical mass of propanoic acid obtained
= 0.267 mol (12.0 3 + 1.0 6 + 16.0 2) g mol1
= 19.8 g [1]
Percentage yield of propanoic acid =
94
14.5 g
100% = 73.2% [1]
19.8 g
(a) Assume there were 100 g of maltose, then there would be 42.1 g of carbon, 6.4 g of hydrogen and
51.5 g of oxygen.
C
42.1
6.4
51.5
42.1
3.5
12.0
6.4
6.4
1.0
51.5
3.2
16.0
3.5
1.1 [1]
3.2
6.4
2 [1]
3.2
3.2
1 [1]
3.2
Masses (in g)
[1]
(iii) There are 4 chiral carbon atoms in a glucose molecule. [1]
[1]
95
(a)
glucose [1]
(b)
(c)
(d)
(e)
fructose [1]
The aldehyde group of glucose is oxidized by acidified potassium dichromate solution and the
solution changes from orange to green. [1] However, there is no reaction between fructose and
acidified potassium dichromate solution and thus no observable changes are made. [1]
96
(a) (i)
If the hydrocarbon chain of the fatty acid contains no carbon-carbon double bond, it is a
saturated fatty acid. [1]
If the hydrocarbon chain of the fatty acid contains one or more carbon-carbon double bonds,
it is an unsaturated fatty acid. [1]
(ii) Palmitic acid is a saturated fatty acid. [1]
(iii)
[1]
(b) The carbon-carbon double bonds in animal fats adopt trans configuration. [1] This causes the
triglyceride molecules to pack more efficiently. [1] As a result, animal fats have higher melting
points and are usually solids at room temperature. [1]
97
(a) Linoleic acid is an unsaturated fatty acid because its hydrocarbon chain contains carbon-carbon
double bonds. [2]
(b) The mole ratio of glycerol to linoleic acid is 1 : 3. [1]
(c)
[1]
(d) Add bromine water to the triglyceride mentioned in (b). [1] If the bromine water is decolorized, the
triglyceride molecules should be unsaturated. [1]
(e) The carbon-carbon double bonds in corn oil adopt the cis configuration. [1] This causes the
triglyceride molecules to pack less efficiently. [1] As a result, corn oil has a lower melting point
and is a liquid at room conditions. [1]
98
99
[1]
[1]
[1]
[1]
(d) (i)
[1]
(ii)
[1]
100
[1]
[1]
[1]
(d)
[1]
There is no chiral carbon atom in the amino acid molecule, so it does not exhibit enantiomerism.
[1]
101
(a)
[3]
(b) The functional groups of aspirin include benzene ring, carboxyl group and ester group. [3]
(c) Aspirin has an anti-inflammatory effect and an anti-platelet effect. [2]
(d) Stomach upset and ulcer [1] or increased bleeding [1]
102
(a)
[1]
(b) Dilute hydrochloric acid/Dilute sulphuric acid [1]
(c) The overall yield of the conversion = 70% 95% = 66.5% [1]
(a)
[1]
(b)
[2]
(c) It has an anti-inflammatory effect and an anti-platelet effect. [2]
(d) Since aspirin is acidic, large dosage will cause stomach upset and ulcer.
Magnesium hydroxide is used to neutralize the acidity. [2]
104
105
[1]
(c) Any TWO of the following:
Carboxyl group [1]
Ester group [1]
Benzene ring [1]
(d) Any TWO of the following:
Relieving pain [1]
Reducing inflammation and fever [1]
Reducing the risk of heart attack [1]
(e) Any TWO of the following:
106
(a)
[2]
(b) Ester linkage [1]
(c) (i) If the hydrocarbon chain contains no carbon-carbon double bond, it is a saturated fatty acid.
[1] If the hydrocarbon chain contains one or more carbon-carbon double bonds, it is an
unsaturated fatty acid. [1]
(ii) Stearic acid is a saturated fatty acid. [1]
(d) (i) CH 3 (CH 2 ) 16 COONa+ [1]
(ii) It is a soapy detergent. [1]
107
(a) (i)
Stearic acid is a saturated fatty acid because its hydrocarbon chain contains no carbon-carbon
double bond. [2]
(ii)
[1]
(b) (i) Sodium hydroxide solution [1] and boiling [1]
(ii) Add the detergent into a solution containing calcium ions or magnesium ions. [1] If lather is
observed, the detergent is a soapless detergent. [1] If scum is observed, the detergent is a
soapy detergent. [1]
108
[1]
(iii) Water [1]
(b) (i) Coconut oil is boiled with sodium hydroxide solution. [1]
(ii)
[2]
109
A detergent enables water to wet the object thoroughly. [1] The hydrophobic tails of detergent anions
dissolve in grease. [1] Water molecules attract the hydrophilic heads of detergent anions, lifting up the
grease from the surface. [1] By stirring, the grease is broken down into tiny droplets, forming an
emulsion. [1]
110
foam
tiny oil droplets
emulsion
Correct drawing [1]
Correct labelling [1]
(d) Yes, it can. It is because soapless detergent will not combine with Ca2+ ions or Mg2+ ions to form
scum in sea water. [2]
111
(a)
[2]
(b) (i)
[1]
(ii)
[2]
(c) (i)
Soapy detergents are made from fats or oil while soapless detergents are derived from
petroleum. [2] Soapy detergents are sodium/potassium salts of long-chain carboxylic acids
while soapless detergents are sodium salts of long-chain alkylbenzenesulphonate or
alkylsulphate. [2]
(ii) The detergent formed in (b)(ii) is a soapy detergent. [1]
(iii) The detergent enables water to wet the clothes thoroughly. [1] The hydrophobic tails of
detergent anions dissolve in grease. [1] The hydrophilic heads of detergents anions are
attracted by water molecules, then the grease is lifted off from the surface of clothes. [1] By
stirring, the grease forms tiny droplets which disperse throughout water to form an emulsion.
[1] The lather produced when mixing detergent and water also helps to suspend grease which
can then be easily washed away. [1]
(iv) No, it does not. [1] It is because the detergent anions form insoluble substance with calcium
and/or magnesium ions. [1]
112
113
(a) A detergent is a substance which helps water to clean things better. [1]
(b) Animal fats and vegetable oils. [2]
(c) A soapy detergent particle contains an ionic group (the head)/a carboxylate group [1] and a
hydrocarbon chain (the tail). [1]
The ionic group is hydrophilic/water-loving/soluble in water. [1]
The hydrocarbon chain is hydrophobic/water-hating/insoluble in water/soluble in oil. [1]
(d) The ionic heads (usually negatively charged) will dissolve in water and the hydrocarbon tails will
dissolve in oil. [1] Therefore, the surfaces of all oil droplets are negatively charged. [1] The oil
droplets repel each other and cannot join together. [1]
114
(a) (i)
Compounds A and C are soapy detergent particles. [2] Because both of their ionic heads are
(a) (i)
Hard water is water that contains considerable concentrations of calcium and/or magnesium
ions. [1]
(ii) It is because soapy detergent anions form insoluble substances with calcium and/or
magnesium ions. [1] Therefore, they will lose their cleaning action.
Ca2+(aq) + 2CH 3 (CH 2 ) 16 COO(aq) (CH 3 (CH 2 ) 16 COO) 2 Ca(s) [1]
(iii) Washing soda contains carbonate ions which react with calcium ions to form insoluble
calcium carbonate. [1] Therefore, calcium ions are removed and the hardness of water is
reduced. [1]
118
(a) It is a soapy detergent. [1] Because its ionic head is carboxylate group. [1]
(b) The ionic head of the detergent particle is hydrophilic [1] while the hydrocarbon tail is
hydrophobic. [1]
(c) His suggestion is incorrect. [1] Since sea water contain considerable concentrations of calcium
ions and/or magnesium ions, the soapy detergent anions can form insoluble scum with these ions.
[1] Therefore, the soapy detergent will lose its cleaning power. [1]
119
(a) Z should be a soapy detergent. [1] It is the only one which forms scum with magnesium ions. [1]
Only soapy detergents form scum with magnesium ions. [1]
(b) X could cause skin allergies. [1] It has a low pH value of 3. It is too acidic for our skin. [1]
(c) Y. [1] It has a pH value of 7 which is as neutral as water. It could not cause skin allergies. [1] It
does not form scum in hard water, so it can work well in hard water. [1] It is biodegradable, so it
causes less environmental problems. [1]
120
[1]
[1] OR
[1]
##
(a) The general repeating unit of nylon: