Review questions

ow fast? rates

Answers

Answers to Topic 1 Review questions

1 a) Labelled axes (1); accurate plot (1); smooth curve (1).
b) Three half-lives = 40 103s (2); half-life of first order reaction independent of
initial concentration (1).
c) Method of calculating gradient (1); values for gradients (2); units: moldm3s1
(1).
d) Axes (1); accurate plot with straight line (1).
k = 1.8 105 (1); s1 (1).
2 a) Axes (1); plot and curve (1).
Half-life from 20 103moldm3: 3.6 103s (1)
Half-life from 12 103moldm3: 7.6 103s (1)
Lower starting concentration high half-life (1).
b) Tangents drawn (1); gradients calculated (1); concentration units included (1).
c) Options:
Plot a concentrationtime graph and take a series of readings from the graph to
show that it takes the form y = x2
plot 1/[A]t against time to get a straight line if the reaction is second order,
where [A]t is the concentration at time t
plot log(rate) against log(concentration) to get a graph with gradient 2.
Choice of method (1); plot (2); explanation (2).
3 a) H2O2(aq) + 2H+(aq) + 2I(aq) 2H2O(l) + I2(aq) (1).
b) Rate = k[H2O2(aq)][I(aq)] (2)
c) Second order (1)
d) The first step (1); which includes the two species which feature in the rate
equation (1).
4 a) i) Changing [X] does not affect the rate (1); zero order (1).
ii) Rate quadruples if [Y] doubles (1); second order (1).
b) Rate = k[Y]2 (2)
c) k =

(1 104 moldm3 s1 )
(1 101moldm 3 )2

= 1 102 (1)dm3mol1s1 (1)

d) Rate-determining step involves two Y molecules (1).
Y + Y Y2
slow (1)
Y2 + X XY2 fast (1)
e) Range of answers possible (1 mark for each point made up to 5). Such as:
rate equations help to deduce reaction mechanisms; this information can inform
methods of chemical synthesis, understanding enzyme action and other
biochemical processes, and hence guide drug design and development
rate measurements are important in controlling chemical changes in laboratory
and industrial processes; chemical engineers use rate data when designing
chemical plants.
5 a) The clock procedure measures the initial rate in this case by finding the time
taken for a small, fixed amount of iodine to form (1). At first the thiosulfate ions
immediately turn the iodine back to iodide ions (1); but once all the thiosulfate is

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used up the iodine produces a deep blue-black colour with the starch indicator
(1).

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b) Completion of table (3):

Temperature, T/K

288

292.5

299

308

315

Time, t, for the blue colour to appear/s

10.0

7.0

5.0

3.5

2.5

ln (1/t)

2.30

1.95

1.61

1.25

0.92

0.00347

0.00342

0.00334

0.00325

0.00318

1/T /K

Plot of graph of ln(1/t) against 1/T with appropriate scales and accurate linear plot
(3).
Gradient = 4180K (1) =

Ea
R

Ea = 35kJmol1 (1)
c) The catalyst provides an alternative reaction pathway with a lower activation
energy (1). One possible alternative route is that when the catalyst is present the
iron(III) ions oxidise iodide ions to iodine (1) and that peroxodisulfate( VI) ions then
oxidise the resulting iron(II) ions back to iron(III) thus regenerating the catalyst.
(1). Perhaps the negative peroxodisulfate( VI) ions react more readily with positive
iron(II) ions than with negative iodide ions (1).

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Answers to Topic 2 Review questions

1 a) At 0K water is solid and the atoms
are highly ordered. (1); The crystals
are not disrupted by molecular
movement (1).
b) The rises in entropy at T1 and T2
correspond to the changes of state:
melting and vaporisation (1).
There is a greater increase in
disorder when molecules separate
from a liquid and turn to gas than
when molecules melt (1); because of
the much greater freedom of
movement of molecules in the gas
phase (1).
c) Water and steam are in equilibrium
(1);
at 373K and 1 atmosphere pressure
so there is no tendency for the
change to go in either direction (1).
d) Stotal = Ssystem + Ssurroundings (1)
Since Stotal = 0kJmol1 and
Ssurroundings = H/T (1)
it follows that Ssystem = H/T (1)
41.1kJmol1
Ssystem =
(1)
373K
= 0.110kJmol1K1
= 110Jmol1K1 (1)
2 a) Al2O3(s) + 3C(s) 2Al(s) + 3CO(g)
(1)
b) Total enthalpy change of formation of
products = 3 (111kJmol1)
= 333kJmol1 (1)
Total enthalpy change of formation of
reactants = 1669kJmol1 (1)
Overall enthalpy change for the
reaction
= (333kJmol1) (1669kJmol1)
= +1336kJmol1 (1)
c) Total entropy of products
= (2 28.3Jmol1 K1) + (3 198J
mol1K1)
= 651Jmol1K1 (1)
Total entropy of reactants

= 50.9Jmol1K1 + (3 5.7 Jmol1

K1)
= 68Jmol1K1 (1)
Overall entropy change of the system
= 651Jmol1K1 68Jmol1 K1 (1)
= 583Jmol1K1

d) i) Entropy change of the

surroundings
1336000J mol1
=
298K
= 4483Jmol1K1 (1)
The total entropy change
= 583Jmol1K1 4483Jmol1
K1 (1)
= 3900Jmol1K1
ii) The reaction is not feasible at 298
K because the total entropy
energy change is negative (1).
e) The reaction becomes feasible when:
Ssystem

Hreaction
>0
T

TSsystem > Hreaction (1)

This just happens when T =
1336
kJmol1
0.583
kJmol1 K 1

= 2292K (1)
f) Reactions between solids are slow.
The reaction has to be very high for
it to proceed at a measurable rate
(1).
519000J mol1
3 a) i) Ssurroundings =
298K
= +1742Jmol1K1 (1)
Stotal
= + 82Jmol1K1 +
1
1742Jmol K1
= +1824Jmol1K1 (1)
ii) The total entropy change is
positive so the reaction is feasible
(1).
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iii) At 298K the activation energy of

the reaction is too high (the bonds
in the molecules are too strong)
(1) and the energy of collisions
between molecules too low for the
reaction to happen at a
measurable rate (1).
b) In the reaction forming CO and
steam, 2.5mol gases react to form 3
mol of gas (1). This increases
disorder so that the entropy change
is substantially positive (1).
In the reaction forming soot, 2mol
gases react to form an ordered solid
and 2mol gas (1). Overall there is
little change in entropy (1).

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4 a)

b) Hsolution[CaCl2(s)]
= (2258kJmol1) 1657kJmol1
+ (2 340kJmol1) (1)
= 79kJmol1
(1) for 79; (1) for sign and units
c) The Ca2+ ion has a higher charge and a larger radius than Li +. The higher charge
will tend to make its electron density greater than Li+ (1); but its larger radius will
tend to make its electron density less than Li+ (1).
d) Water molecules are polar with a + charge between the H atoms and a charge
on the O atom (1). The + charge attracts anions and the attracts cations (1);
so hydration is an exothermic process and the hydration enthalpies of both anions
and cations are negative (1).

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Answers to Topic 3 Review questions

1 a) Kc =

(0.07
moldm3 )2
(1)
3
(0.01
moldm ) (0.01
moldm 3 )
= 49 (1); no units (1)
b) i) The quantity of iodine that has
reacted
= 0.003moldm3
This reacts with 0.003moldm3
hydrogen and produces 0.006mol
dm3 HI.
So the new concentrations are:
[H2(g)] = 0.017moldm3 (1); and
[HI(g)] = 0.076moldm3 (1).
ii) Substituting in the expression for
Kc gives

c)

2 a)

b)

c)

(0.076
moldm3 )2
(0.017
moldm3 ) (0.007
moldm3 )
(1)
= 48.5
This is very close to the value for
Kc calculated in a). The system is
again at equilibrium (1).
Doubling the hydrogen concentration
causes a shift in the position of
equilibrium to the right giving more
HI and less iodine (1); some, but not
all, of the added hydrogen reacts (1).
17
Concentration =
0.50 mol dm3
10
(1)
= 0.85moldm3 (1)
6.0
Concentration =
0.01mol
10
dm3 (1)
= 0.006moldm3 (1)
0.85moldm3
Kc =
= 140 (1); no
0.006
moldm 3
units (1)

4
2
2
[Sn
(aq)][Fe
(aq)]
3 a) i) Kc =
(2)
2
3
2
[Sn
(aq)][Fe
(aq)]

ii) Kc has no units (1); the

concentration terms cancel (mol
dm3)3 appears on the top and the
bottom of the expression for Kc
(1).
b) i) The reciprocal of the value given
in the question (1): Kc = 1 1010
(1).
ii) The square root of the value given
in the question (1): Kc = 1 105
(1).
4 a) At equilibrium the forward and
backward reactions happen at the
same rate so that overall there is no
change (1). Nitrogen and hydrogen
react to form ammonia as fast as
ammonia decomposes back to
nitrogen and hydrogen (1).
b) i) Mole fractions: NH3, 0.137 (1);
H2, 0.655 (1); N2, 0.209 (1)
ii) Partial pressures: NH3, 1.37atm;
H2, 6.55atm; N2, 2.09atm (2)
iii) Kp =

( pNH3 )2
pN2 ( pH2 )3

(1)

= 3.20 103 (1); atm2 (1)

c) Stotal =Ssystem

Hreaction
(1)
T

H is negative and so the total

entropy change gets smaller as T
rises (1).
Stotal =R ln K (1)
This means that Kp gets smaller as T
rises (1).
As a result, the mole fraction of
ammonia decreases and the mole
fractions of nitrogen and hydrogen
increase as T rises (1).

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Answers to Topic 4 Review questions

1 a) Kc =

[PCl3(g)][Cl
2(g)]
(1)
[PCl5(g)]

1
= 125 (1) (1)
8 10 moldm3
dm3mol1

b) Kc =

2 a)

c) [PCl3(g)] = [Cl2(g)] = x (1)

x2
= 8 103mol
2
3
5 10 moldm
dm3 (1)
x = 2 102moldm3 (1)
d) i) Some, but not all, of the added
PCl5 decomposes (1) and
increases the concentrations of
PCl3 and chlorine (1).
ii) Increasing the pressure causes
the equilibrium to shift in the
direction that gives fewer moles
of gas (1); so the concentration of
PCl5 increases while the
concentrations of PCl3 and
chlorine decrease (1).
iii) Raising the temperature causes
the equilibrium to shift in the
direction that is endothermic (1);
so the concentration of PCl5
decreases while the
concentrations of PCl3 and
chlorine increase (1).
e) i) Changing concentrations does not
affect the value of Kc (1).
ii) Changing the pressure does not
affect the value of Kc (1).

b)

c)

d)

iii) Kc increases (1). For an

endothermic reaction the value of
Kc gets larger as the temperature
rises (1).
Chemical equilibrium is dynamic (1);
on a molecular scale there is
constant change with opposing
reactions cancelling each other out
(1). However, the overall
macroscopic effect is that nothing
appears to be changing when the
system is at equilibrium (1).
Kc does not vary with concentration
(1). However, it is true that adding
more of a reactant to a system at
equilibrium means that the mixture
is no longer at equilibrium (1); some
of the added chemical reacts and
more products form until the system
is again at equilibrium (1).
Adding a catalyst does not affect the
value of Kc (1). At a constant
temperature, the yield of product at
equilibrium is not changed by adding
a catalyst (1); however, many
processes are so slow that they never
reach equilibrium in the absence of a
catalyst, so in that sense an added
catalyst increases the yield by
enabling the reaction mixture to
reach equilibrium (1).
This is true if the reaction to make
products is endothermic (1). If the
reaction is exothermic, then the
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equilibrium yield of product falls as

the temperature rises (1). However,
as with catalysts, raising the
temperature can increase the yield of
a product by allowing a reaction
mixture to reach equilibrium that
reacts too slowly at room
temperature (1).
e) A reaction is feasible in the
thermodynamic sense if the total
entropy change for the process is
positive (1). Adding a catalyst
speeds up the rate of reaction but
cannot change the feasibility of a
reaction at a particular temperature
(1). Only if the reaction is not going
because it is kinetically inert can a
catalyst enable a reaction to happen
at a particular temperature (1).
3 a) Kp =

pCO ( pH2 )3
pCH4 pH2O

(2)

b) i) Kp does not change (1).

ii) Kp increases (1).
iii) Kp does not change (1).
the reactor and hence the mass of
product produced in a given time
from a given piece of plant (1).
(The chosen pressure also depends
on the price of platinum. Working at
higher pressures increases the wear
on the catalyst and shortens the life
of the catalyst gauzes.)
d) The gases flow through the solid
catalyst gauzes and so the catalyst is
used continuously and does not have
to be recovered from the reaction
mixture (1).
e) The gases flow through the catalyst
gauzes so the mixture of product and
unchanged reactants is only in
contact with the catalyst for a short
time (1); as soon as the gases flow
away from the catalyst reaction stops
the mixture has time to approach

c) i) Concentration of products
decreases and the concentration
of reactants increases (1).
ii) Concentration of products
increases and the concentration of
reactants decreases (1).
iii) Composition of the equilibrium
mixture does not change (1).
4 a) 4NH3(g) + 5O2(g)
4NO(g) +
6H2O(g) (2)
b) In theory the yield of NO at
equilibrium is high if the
temperature is low (1) and the
pressure low (1); adding excess
oxygen also favours the conversion of
ammonia to NO (1).
c) There is an excess of oxygen (even
though only a fifth of the air is
oxygen) (1). The temperature has to
be high because reaction only
happens at a practicable rate if the
catalyst is hot (1). Raising the
pressure compresses the gases and
this increases the mass of material
flowing through
equilibrium but not reach
equilibrium (1).
f) The hot gases flow though a heat
exchanger where they turn water to
hot steam (1); that can be used in
other processes or to generate
electricity (1).

5 a) In a simple addition reaction two

chemical combine to form a single
product (1); so all the reactant
molecules end up in the product the
atom economy is 100% (1); example
(1).
In any substitution reaction there is
at least one other chemical formed in
addition to the desired product (1);
example (1).
b) The yield of a reaction measures the
amount of product made compared

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with the amount expected according

to the balanced chemical equation
(1); the calculation of yield takes no
account of the other products of the
reaction. (1); it is possible to have a
very high yield from a reaction with a
low atom economy (1); example used
to distinguish yield from atom
economy (2).
c) Changes in temperature affect both
the rate of reaction (1); and the

composition of the equilibrium

mixture (1); reactions have to go fast
enough to produce product from a
chemical plant at an economic rate
(1); in practice this can mean that
the temperature has to be higher
than would otherwise be chosen to
maximise the percentage of product
in the equilibrium mixture. (1);
example explained (1).

Answers to Topic 5 Review questions

1 a) HX(aq)
b) Ka

H+(aq) + X(aq) (1)

[H (aq)][X
(aq)]
(1)
[HX(aq)]

c) i) As the temperature rises the equilibrium shifts in the direction that is

endothermic. So the acid ionises more as the temperature rises and this is
because the value of Ka increases (1).
ii) Since the acid ionises more as the temperature rises, the hydrogen ion
concentrations rises and the pH decreases (1).
iii) Ka will not change. Ka is a constant and only varies if the temperature changes
(1).
2 a) A buffer solution evens out the large swings in pH which can happen without a
buffer (1).
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A typical buffer mixture consists of a solution of a weak acid and one of its salts,
for example a mixture of ethanoic acid and sodium ethanoate (1); there must be
plenty of both the acid and its salt in the buffer mixture (1).
Adding a small amount of strong acid temporarily increases the concentration of
H+(aq) so the equilibrium shifts to the left to counteract the change (1); adding a
small amount of strong alkali temporarily decreases the concentration of H +(aq) so
the equilibrium shifts to the right to counteract the change (1).
The pH of blood, for example, is closely controlled by buffers within the narrow
range 7.35 to 7.45. Chemists use buffers when they want to investigate chemical
reactions at a fixed pH (1).
b) i) [H+(aq)]
=
3
0.08mol
(1)dm
1.7 105moldm3
0.04moldm 3
= 3.4 105 mol dm3
pH = 4.5 (1)
ii) [H+(aq)]
= 1.7 105moldm3

0.06moldm3
(1) = 1.7 105 mol dm3
3
0.06moldm

pH = 4.8 (1)

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6 Stereochemistry

1 1014 mol2 dm6

0.02moldm 3
= 5.0 1012 mol dm3 (1)
pH = 11.3 (1)
iv) The change of pH is very much less when adding the alkali to a buffer solution
than when adding it to water (1).
Strong acid ionises completely in aqueous solution (1). An example is
hydrochloric acid: HCl(aq) H+(aq) + Cl(aq) (1)
A weak acid only ionises to a slight extent in solution (1). An example is ethanoic
acid:
CH3COOH(aq)
H+(aq) + CH3CO2(aq) (1)
i) 2 (1)
ii) [OH(aq)] = 0.01moldm3
1 1014 mol2dm6
[H+(aq)]
=
0.01moldm 3
12
= 1 10 moldm3 (1)
pH = 12 (1)
(1.5
105 0.02)
moldm3 (1)
i) [H (aq)]
pH = 3.3 (1)
ii) Line of sketch graph rises at first from pH = 3.3; partly levels off through buffer
region (1); then rises to give a steeply rising curve when the titre is 25cm 3 (1)
; half-way up the steeply rising portion is above
pH 7 (1); the curve then levels off at about
pH 12 (1).
iii) Thymolphthalein (1) full colour change must take place within the steeply
rising part of the curve (1).
i) HClO(aq)
H+(aq) + ClO(aq) (1)
iii) [H+(aq)]

3 a)

b)

c)

4 a)

Answers

ii) Ka =

[H (aq)][ClO
(aq)]
(1)
[HClO(aq)]

b) [H+(aq)] = 107.43 (1) = 3.7 108moldm3 (1)

(3.7 108 moldm3 )(0.050

moldm3 )
Ka =
(1)
0.050
moldm 3
= 3.7 108 mol dm3 (1); pKa = 7.4 (1)

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6 Stereochemistry

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Answers to Topic 6 Review questions

1 a) Two structural isomers with the
same functional groups (1);
structures of
1-chloropropane and
2-chloropropane (1).
b) Six structural isomers/EZ isomers:
one with F on the C atom with H,
one with the Cl on that atom, and
one with the Br on that atom. Then
each of these can have EZ isomers
(6).
c) Two EZ isomers: the E isomer has
the Br and Cl on opposite sides of
the double bond (1), while the Z
isomer has them on the same side
of the double bond (1).
2 a) A chiral centre is typically a carbon
atom with four different groups
around it (1); in general a molecule
is chiral if it is asymmetric.
b) The mirror image forms or a chiral
molecule cannot be superimposed
on one another (1); they have
opposite effects as they rotate the
plane of plane-polarised light (1).
c) Only CH3CHOHCOOH is chiral and
can exist as two optical isomers
(1); the other two compounds both
have two hydrogen atoms on the
central carbon atom .
d) A racemic mixture contains equal
amounts of the two optical isomers
(1); the two isomers rotate the
plane of plane-polarised light
equally but in opposite directions
so their effects cancel (1).
e) i) C13H21O3N (1)
ii) There is one chiral carbon atom:
(1)

3 Stereoisomerism involves molecules

with the same molecular formula (1);
and the same structural formula (1);
but different three-dimensional
shapes (1); in which their atoms
occupy different positions in space
(1).
There are two forms of
stereoisomerism.
EZ (cis/trans) isomerism (1); which
occurs principally in alkenes and
other compounds with C=C double
bonds (1).
In EZ isomerism, the Z-isomer has
atoms, attached to the C atoms of the
double bond, with higher atomic
number (1) on the same side of the
double bond (1).
In the E-isomer, atoms attached to the
C atoms of the double bond with
higher atomic number are on opposite
sides of the double bond (1). An
example of EZ isomerism is 1,2dibromoethene.
Named structures of the E and Z
isomers (2).
Optical isomerism (1) involves nonsuperimposable mirror images (1). In
most cases, this requires the
molecules to possess a C atom with
four different atoms or groups
attached to it (1).
These mirror images are labelled (+)
and () forms (1).
The (+) form rotates plane-polarised
light clockwise (1) and the () form
rotates plane-polarised light
anticlockwise (1).
A named example of optical
isomerism (1); e.g. alanine or
bromochlorofluoromethane.
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Diagram showing structures of the

optical isomers of the example
suggested as mirror images (1).

[Any 15 of these or other legitimate

points]

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Answers to Topic 7 Review questions

1

Reactant

CH3CH2CHO

Reagent

Organic product
Name

Tollens reagent

Displayed formula

propanoic acid (1)

(1)

CH3CH2CHO

Cr2O72/H+ (1)

propanoic acid
(1)

CH3CH2CHO

LiAlH4

propan-1-ol (1)
(1)

2 a) C10H16O (1)
b) i) Carboncarbon double bond as in an alkene (1); aldehyde group (1).
ii) Ketone group (1).
c) i) The blue reagent gives an orange-brown precipitate (1) with citral; but not
with -ionone (1).
ii) The reagent gives a bright orange precipitate (1); with citral and with -ionone
(1).
iii) The reagent gives a pale yellow precipitate (1) with -ionone; but not with
citral (1).
d) i) The structure stays the same except that the ketone group is reduced to a
secondary alcohol; the side chain attached to the ring becomes
CH=CHCHOHCH3 (1).
ii) The structure stays the same except that the aldehyde group is oxidised to a
carboxylic acid group COOH (1).
e) i) Both compounds have EZ isomers (1).
ii)

(1)

Z-citral (1)
iii) Neither compound has a chiral centre and so neither has optical isomers (1).
3 a) W: empirical formula CH2, molecular formula C4H8 (1); could be but-1-ene or but2-ene (1); because both give 2-bromobutane when they add HBr.
X: 2-bromobutane (1); because it hydrolyses to butan-2-ol (1).
Y: butan-2-ol (1); a secondary alcohol because it oxidises to a ketone (1).
Z: butanone (1); a ketone because it does not react with Benedicts reagent (1).

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b) CH3CH=CHCH3(l) + HBr(g) CH3CH2CHBrCH3(l) (1).

CH3CH2CHBrCH3(l) + NaOH(aq) CH3CH2CHOHCH3(l) (1).
CH3CH2CHOHCH3(l) + [O] CH3CH2COCH3 (l) (1).
4) Equations to describe the mechanism of addition to C=C and C=O (2 2)
Propene with bromine

HCN with propanone

Addition reaction

Similarities

Heterolytic bond breaking

Two-step process (any 2)

Differences

Electrophilic reagent

Nucleophilic reagent

Attacks electron-rich bond

Attacks + end of polar C=O bond

Intermediate is a positive ion (any 2)

Intermediate is a negative ion (any 2)

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8 Carboxylic acids and their derivatives

Answers

Answers to Topic 8 Review questions

1 Butane is non-polar. The only
intermolecular forces are weak London
forces. It has the lowest boiling
temperature: 273K (1).
Propanal has a polar C=O bond and so
there are attractions between
permanent dipoles as well as London
forces. It boils at a higher temperature
than butane: 322K (1).
Hydrogen bonding is the strongest type
of intermolecular force. Hydrogen
bonding is possible between the
molecules of ethanol and between the
molecules of ethanoic acid (1).
There is greater scope for hydrogen
bonding in ethanoic acid with the OH
group and O atom in the carboxylic acid
group. Hence both compounds boil at a
higher temperature than propanal, but
ethanoic acid boils at a higher
temperature (391K) than ethanol (371
K) (1).
2 a) Propanoyl chloride, CH3CH2COCl (1)
b) Butan-1-ol, CH3CH2CH2CH2OH (1)
c) Pentan-1-ol, CH3CH2CH2CH2CH2OH
(1); and sodium ethanoate
CH3COONa (1)
d) Calcium ethanoate, (CH3COO)2Ca (1)
e) Methylethyl ethanoate,
CH3COOCH(CH3)2 (1)
3 a) Step 1: Heat under reflux with dilute
hydrochloric acid (1).
Step 2: React with PCl5 at room
temperature (1).
b) CH3CH2CH2COCl (1), butanoyl
chloride (1)
c) Butanamide (1)

(1)
4 a) Possible answers:
reaction with magnesium (1);
colourless flammable gas given off as

b)

5 a)
b)

c)

6 a)

metal disappears (1); reaction much

faster with hydrochloric acid (1).
or
reaction with sodium carbonate
solution (1); colourless gas given off
which turns limewater milky (1);
effervescence much more vigorous
with hydrochloric acid (1).
Acid solutions react in a similar way
because they contain H+(aq) ions
(1).
Mg(s) + 2H+(aq) Mg2+(aq) + H2(g)
(1)
CO32(s) + 2H+(aq) CO2(g) +
H2O(l) (1)
HCl(aq) is a strong acid and so fully
ionised (1); while ethanoic acid is a
partially ionised weak acid (1).
The reactions with HCl(aq) are much
faster because of the higher
concentration of hydrogen ions (1).
C13H18O2 (1).
The carboxylic acid group can form
hydrogen bonds with water (1). The
hydrocarbon part of the molecule is
non-polar and cannot easily break
into the hydrogen-bonded structure
of water (1). The large hydrocarbon
part of the molecule, including a
benzene ring, means that ibuprofen
is only likely to be very sparingly
soluble in water (1).
i) The same as the structure shown
in the question but with the
carboxylic acid group turned into
a sodium salt: COONa+ (1).
ii) The same as the structure shown
in the question but with the
carboxylic acid group turned into
an ethyl ester: COOC2H5 (1).
The saturated fatty acid molecules
have a more regular shape (1); so
they pack together more easily with
a large area in contact for London
forces (1). The double bond in the
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G. Hill and A. Hunt 2009 Edexcel Chemistry for A2

8 Carboxylic acids and their derivatives

Answers

unsaturated compound puts a kink in

d) i) Hydrogen adds across the double
the molecules, which means that
bond to form octadecanoic acid
they do not pack so well and melt at
(1).
a lower temperature (1).
ii) In the cis compound the two
b) A solution of bromine (in water or
hydrogen atoms in the CH=CH
preferably an organic solvent) (1);
are on the same side of the double
turns from orange to colourless (1);
bond with both hydrocarbon
when shaken with unsaturated cischains on the other side (1); in
octadec-9-enoic acid (1); there is no
the trans compound the two
change with the saturated acid.
hydrogen atoms are on opposite
c) It is an ester of propane-1,2,3-triol
sides of the molecule (1).
(1); with three fatty acids (1).
iii) During partial hydrogenation some of the cis unsaturated acids turn to the
trans form (1). There is some evidence that trans acids raise the level of the
harmful form of cholesterol in the blood; the form that can increase the risk of
heart disease. (1)
7 a) A condensation reaction is one in which molecules join together by splitting off a
small molecule, such as water, from two functional groups, such as a carboxylic
acid group and an alcohol group (1); condensation polymers are produced by a
series of condensation reactions between the functional groups of the monomers,
where each monomer has at least two of the reactive functional groups (1).
b) A molecule with two carboxylic acid groups

(1)
A molecule with two alcohol functional groups.

(1)
c) Polyester is used to make fibres and fabrics for clothing and other uses (1).
Polyesters can be melted and spun into fibres which are strong. The fibres in
polyester fabrics do not stretch or shrink (1).

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G. Hill and A. Hunt 2009 Edexcel Chemistry for A2

8 Carboxylic acids and their derivatives

Answers

Answers to Topic 9 Review questions

1
Type of
chromatography

Method of
separation:
adsorption or
relative solubility

Example of an
application

Advantages

Limitations

HPLC

Adsorption (1)

Studying the
metabolism of
drugs in the
body

Can be used to
analyse ionic salts
and also large
biological molecules

Relatively expensive

(1)

Can give quantitative

as well as qualitative
results (1)

Columns cannot be too long

or the pressure needed to
force the liquid through
them is too high and this
can limit the degree of
separation achieved
(1)

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G. Hill and A. Hunt 2009 Edexcel Chemistry for A2

8 Carboxylic acids and their derivatives

GC

Answers

Either adsorption or
relative solubility,
depending on the
type of column
(1)

Investigation
arson,
detecting
pollutants of
water, air and
food
(1)

Very versatile
technique with a
range of types of
column for different
applications
Very sensitive can
analyse very small
samples
Can give quantitative
as well as qualitative
results
(1)

Can only be used to analyse

volatile compounds that do
not decompose in the hot
column
Similar compounds have
similar retention times
making it hard to identify
components unless
combined with MS
Unknowns cannot be
identified because of the
lack of reference data (1)

2 a) i) Three environments (1)

ii) From the integration trace data: 3
: 3 : 2 (1)
b) Peak at = 1.0: RCH3 (1); peaks at
= 2.1 and 2.5: consistent with
H3CCO and RCH2CO (1).
c) Peak at = 1.0: triplet two protons
on an adjacent carbon atom (1).
Peak at = 2.5: quadruplet three
protons on an adjacent carbon atom
(1).
d) The compound is a carbonyl
compound (1). It is a ketone and not
an aldehyde (1). There is no OH
group in the molecule so it is not an
alcohol or acid (1).
e) Butan-2-one

(1)
3 a) Pentan-2-one
one

pentan-3-

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G. Hill and A. Hunt 2009 Edexcel Chemistry for A2