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NOV2005 P3

Suggested Answers and Comments

N05/III/1
1 (a)(i) Rate = k[NO]2[O2]

Comments:
Note that N2O2 is an intermediate and it cannot appear in the rate
equation.

The following is using sequential logic to derive the rate equation.

Since (A) 2NO → N2O2 (fast)


(B) N2O2 + O2 → 2NO2 (slow)

Substituting equation (A) into (B) (since N2O2 comes from 2NO), thus,
(C) (2NO) + O2 → 2NO2

Thus, it appears that the slow step constains two molecules of NO and
1 molecule of O2. Hence rate equation is rate = k[NO]2[O2]

(a)(ii) Rate constant:


The rate constant is represented by the symbol ‘k’ in the rate equation
in (a)(i) and it is affected by temperature and size of activation energy,
and it is independent of the concentration of the reactants.

Order of reaction:
It is given with respect to a given reactant and it is defined as the power
to which the concentration of that reactant raised to in the
experimentally determined rate equation. Using the above rate
equation, the order of the above reaction would be 2 + 1 = 3.

Rate determining step:


If the reaction progresses in a series of steps, the slowest step will be
the rate determining step.

Comments:
Instead of explaining these terms from scratch, it is easier to explain
them with the aid of a rate equation, which you have given in (a)(i).

(b)(i)
Enthalpy/ kJ mol-1
Transition state

Ea = + 79 kJ mol-1

H2O2

Ho = - 98 kJ mol-1

H2O + 1/2O2

Reaction coordinate / progress of reaction

Comments:
All the necessary details in this question are illustrated by the above
diagram. In addition, they are also bolded.

Kwok YL 1
NOV2005 P3

(b)(ii) Activation energy is the minimum amount of energy the reactants need
to possess to enable a chemical reaction to occur.

Comment:
Activation energy isn’t the amount of energy to “kick start” a reaction.
To ‘kick start’ a reaction implies that it is the factor which initiates the
reaction and then the reaction will just run by itself.

Activation energy is the one of the criteria that causes a reaction to run
by it self. Thus, it doesn’t “kick start” the reaction.

(b)(iii) The catalyst participates in the reaction by looking for another reaction
pathway which has a lower activation barrier.

This results in more number of reactants, at the same temperature, to


have possessed the minimum energy for reaction to proceed. The
number of effective collisions increase and hence rate increases.

Comments:
A catalysed reaction is faster not only because the energy barrier of the
reaction is lowered. More importantly, more molecules possess that
minimum energy requirement for the reaction to proceed.

(b)(iv) The rate constant will increase.

Since, using the catalyst the reaction rate becomes faster, despite the
concentration of reactants remains the same. Hence, using the rate
equation, the rate constant increases.

Ea

In addition, with reference to the Arrhenius equation: k = Ae RT
, the
smaller the Ea, the larger the k value.

Comments:
Having the knowledge of Arrhenius equation will conveniently assist you
in answering this question.

If you cannot remember this equation, you can use the rate equation
and logically deduce that the rate constant would increase when Ea
decreases.

N05/III/2
2 (a)(i) Formula Mass of NaClO3 = 23 + 35.5 + 3(16) = 106.5

n(NaClO3) = 1 x 106/106.5 = 9389 ≈ 9390 moles


Since ClO3- ≡ 6 e-
n(e-) = 6 x 9389 = 56338 ≈ 56 300 moles
Q = It
56 338 x 96500 = I x (24 x 60 x 60)
I = 6.29 x 104 A

Comments:
Students need to remember to do convert time from day to seconds. A
step wise manner to calculate this answer is needed for coherence of
answer.

Kwok YL 2
NOV2005 P3

(a)(ii) Since current passing through the cathode is the same as the anode.

n(e-) = 56 338 moles


H2 ≡ 2 e-
n(H2) = 0.5 x 56 338 = 28 169 ≈ 28 200 moles
volume of H2 = 28 169 x 24 ≈ 6.76 x 105 dm3

Comments:
The same amount of current passing through the cathode and anode.
Therefore, this enables them to know the amount of electrons flowing
from cathode and anode. Thus enable the calculation of the volume of
H2 produced.

In addition, do remember that at room temperature pressure, which is


25 oC and 1 atm, the molar volume of gas is 24 dm3.

It is at 273 K and 1 atm, where the molar volume of the gas is 22.4 dm3.

(b)(i) Sr(IO3)2 (s) Sr2+(aq) + 2IO3-(aq)

Ksp = [Sr2+][IO3-]2

Units: mol3 dm-9

Comments:
Calculation of units:
Units of concentration = mol dm-3

Units of Ksp = (mol dm-3)(mol dm-3)2


= (mol dm-3)(mol2 dm-6)
= mol3 dm-9

The Kc expression is not suitable because it includes a concentration of


Sr(IO3)2 solid, which is a constant. Thus, re-writing the expression
would give the Ksp expression.

(b)(ii) Let solubility of Sr(IO3)2 be x


Therefore, this implies that [Sr(IO3)2 (aq)] = x. [Sr2+] = x, [IO3-] = 2x

1.1 x 10-9 = x(2x)2 = 4x3


=> x = [Sr2+] = 6.5 x 10-9 mol dm-3

Comments:
I have obtain the concentration of [Sr2+] and [IO3-] by the following:
2+
Sr(IO 3)2 (s) Sr (aq) + 2IO 3 (aq)

i / mol dm -3 0 0
-3
e / mol dm x 2x

Where x is solubility of Sr(IO3)2

Note 1: All aqueous ionic compounds will fully dissociate into its
component ions.

Kwok YL 3
NOV2005 P3

N05/III/3 Either
3E (a) Lattice energy is the energy evolved when 1 mole of solid ionic
compound is formed from its respective component gaseous ions when
the ions are infinitely apart.

Comments:
This question calls for the definition of lattice energy. Do note that it is
for 1 mole of ionic compound formed.

Do not be confused with using the following equation and answer:


q+q−
LE ∝
r+ + r−

Lattice energy measures the strength of the ionic bond between


opposite charge ions. The larger the charges (represented by the letter
q) of the respective ions and smaller the radius (represented by the
letter r) of the respective ions, the stronger the ionic bond.

This is the answer when you are asked about the factors affecting LE.

(b)(i) Mg2+ (g) + O2-(g) → MgO (s)

Comments:
Question implies a chemical equation. Take note of state symbols as
well, since it is an equation for a thermochemistry question.

(b)(ii) Mg (s) + ½O2 (g) → MgO (s)

Comments:
Take note of the state symbols of the reactants and products. Do
remember that enthalpy change of formation is the heat change due to
the formation of 1 mole of MgO.

(c) LE
Mg2+ (g) + O2-(g) MgO (s)

2nd Ionisation Energy of Mg 2nd Electron Affinity


of O

Mg+ (g) + O-(g)


1st Electron Affinity
st
1 Ionisation Energy of Mg of O ∆Hf (MgO)

Mg (g) + O (g)

∆Hatm (Mg) ½ Bond Energy (O=O)

Mg (s) + ½O2 (g)


LE = ∆Hf (MgO) - ∆Hatm (Mg) - ½ Bond Energy (O=O) – (1st + 2nd IE) –
(1st + 2nd Ea)
= (-602) – (+148) - ½(+496) – (+736 + (+1450)) – (-140 + (+798))
= - 3840 kJ mol-1

Kwok YL 4
NOV2005 P3

Comments:
Note that you are not given the ∆Hatm (O). But this is equivalent to the
½ Bond Energy (O=O). Do note that O2 exists as a double bond linking
two O atoms.

(d) Ca2+ and Mg2+ has the same charge, but Ca2+ has a larger radius than
Mg2+

Using the relationship below,

q+q−
LE ∝
r+ + r−

Thus, the larger the cation the smaller the lattice energy. Hence, MgO
as a larger lattice energy than CaO.

Comments:
Do note that the correct comparison is to compare the ionic radius and
NOT the atomic radius.

(e) MgO is being used as a furnace lining due to its high melting point.

Comments:
You are to use the effect of high lattice energy of Group II oxides on
their physical property. The only logical physical property that can be
related to lattice energy is melting point.

You shouldn’t be discussing about chemical properties, as it doesn’t


relate to the lattice energy. Neither should you be talking about ease of
thermal decomposition as it is not one of a relevant uses of Group II
oxide.

Kwok YL 5
NOV2005 P3

N05/III/3 Or
3O (a) The energy required to break one mole of a given bond into it
component gaseous atoms/molecules.

Comments:
It is important to stress that it is the energy which breaks 1 mole of a
given bond. It is not the energy needed to convert 1 mole of compound
into its component gaseous atoms.

(b)(i) C8H18 (l) + 12½O2 (g) → 8CO2 (g) + 9H2O (l)

Comments:
Generally: Alkanes with 1 – 4 carbons are gases in room temperature.
While alkanes with 5 – 10 carbons are liquid.

(b)(ii) C8H18 + 12½O2 → 8CO2 + 9H2O

Bond broken: Bonds formed:


7 C–C 16 C = O
18 C – H 18 H – O
12½ O = O

∆HC (C8H18) = 7(+350) + 18(+410) + 12½(+496) – 16(+740) – 18(+460)


= (+16030) – (+20120)
= - 4090 kJ mol-1
Comments:
Remember that enthalpy change of combustion is the heat evolved
when one mole of substance is completely burnt.

Note 1: Formation of CO is due to incomplete combustion!

Note 2: Bond energy for O=O is represented by this equation:


O=O (g) → 2O (g). The reactants are in gaseous state, since you only
want to break the covalent bond and not the IMF.

Note 3: Using bond energies to calculate gives inaccurate enthalpy


change because 1) they are averages and 2) the heat required to
change the reactants to gaseous state is not accounted for.

(c)(i) 1) The bond energies used in the data booklet are averages. Hence, it
results in the difference in the calculated value in (b)(ii) and the table in
(c).

2) The ∆HC of the experiment data refer to enthalpy change of


combustion at standard conditions, which implies that H2O exists as a
liquid. However, the use of bond energies to calculate enthalpy change
of combustion, we have taken H2O to be a gas. Thus, the energy
released due to the formation of strong H-bonding in water is not
accounted for.

3) The C = O bond strength in CO2 is stronger than the C = O that is


quoted in the data booklet.

Choose any one of the three as answer.

Kwok YL 6
NOV2005 P3

Comments:
1) The bond energies in the data booklet are average. The strength of
a covalent bond is also dependent on the type of atom that surrounds
the molecule. Hence, we would expect the C – H bond CH4 to differ
from C2H4. But this is not reflected in your data booklet.

2) To obtain the bond energy of O – H from H2O, H2O must be in


gaseous state. If liquid H2O is used, additional energy would be
required to overcome the hydrogen bonding between H2O molecules.

3) If the C = O bond in CO2 is stronger, it would explain for why the ∆HC
in (c) is more exothermic than your calculation in (b)(ii)

4) I have left out accounting for heat required to vaporize octane


because the bond energy calculation is less exothermic than the
enthalpy change of combustion given by the question.

(c)(ii) The increase in ∆HC from C7H16 to C8H18 to C9H20 is regular.


Approximately, the increase is by a magnitude of 654. Hence, this
value represents the ∆HC of a CH2 unit.

(d) In 1.0 dm3 of ethanol:

Mass of ethanol = 0.79 x 1000 = 790g

n(ethanol) = 790/(2(12) + 6(1) + 16) = 17.2 moles

Heat produced by complete combustion of 1.0 dm3 of ethanol


= 17.2 x 1367 ≈ 23. 5 x 103 kJ (3 S F)

In 1.0 dm3 of octane:

Mass of octane = 0.70 x 1000 = 700g

n(Octane) = 700 / (8(12) + 18(1)) = 6.14 moles

Heat produced by complete combustion of 1.0 dm3 of octane


= 6.14 x 5470 ≈ 33.6 x 103 kJ (3 S F)

Comments:
Care is required when doing conversion of units. The units of density is
given in g cm-3, whereas volume is given in dm3.

Take note that the enthalpy change of combustion is the combustion of


one mole of organic substance (C8H18 and CH3CH2OH)

Kwok YL 7
NOV2005 P3

N05/III/4
4 (a) Elements which forms an ion or compounds with a partially-filled d-
orbital.

Comments:
Students may be tempted to describe the physical properties of
transition elements as a means to define transition elements. Hence, to
state that transition elements merely have variable oxidation states
and/or colours are not suitable definitions. For example, lead has 3
different oxidation states, 0, 2 and 4, but lead is not a transition element.
In addition, I2, Br2, and Cl2 all exhibit colours but neither are any of them
a transition element.

(b)(i) Cr: 1s22s22p63s23p63d54s1

Comments:
Despite 4s is being filled before 3d, do remember that Cr prefers the half
filled d orbitals instead of having 3d44s2.

(b)(ii) Cr3+: 1s22s22p63s23p63d3

Comments:
4s electrons are removed before the 3d.

Hence, 1 electron is removed from 4s and 2 are removed from 3d.


Therefore, providing the above electronic configuration.

(c)(i) The following are the steps:


1. Dissolve the tablet in a 150 cm3 of HCl solution.

2. Pipette out 25.0 cm3 of the solution created in (1) into a conical flask.

3. Add one or two drops of the indicator into the conical flask.

4. Fill the burette with the standard solution of K2Cr2O7. Titrate it until
the solution changes from red to blue.

5. Repeat the titration steps for unit consistent readings are obtained.

6. Calculate the average volume of K2Cr2O7 used.

7. Using this equation


Cr2O72- + 14H+ + 6Fe2+ → 2Cr3+ + 6Fe3+ + 7H2O
Calculate the number of moles of Fe2+ present in 25 cm3 of solution.

8. Calculate the number of moles of Fe2+ that is originally present in the


150 cm3 solution.

Comments:
You have to ensure that the solution is acidified as potassium
dichromate acts as an oxidising agent in acidified medium.

Remember the titration has to be repeated so as to obtain a set of


consistent readings.

Kwok YL 8
NOV2005 P3

(c)(ii) Cr2O72- + 14H+ + 6Fe2+ → 2Cr3+ + 6Fe3+ + 7H2O

n(Cr2O72-) used = (10.50/1000) x 0.025 = 2.625 x 10-4 moles

n(Fe2+) present = 2.625 x 10-4 x 6 = 1.575 x 10-4 moles

n(Fe) = n(Fe2+) = 1.575 x 10-4 moles

Mass of Fe present = 1.575 x 10-4 x 55.8 ≈ 0.0879g (3 S F)

N05/III/5 Either
5E (a) When concentrated H2SO4 is added to:

KCl, white fumes appears.


KBr, brown fumes appears.
KI, purple fumes appears.

Down the group, Cl2, Br2 and I2, the reducing strength decreases.
Hence, this results in I- to be most easily oxidised and Cl- the least.

As a result, concentrated H2SO4 is strong enough to oxidised I- to I2.


It is marginally strong enough to oxidise Br- to Br2, but HBr still remains.
But HBr is white in colour, hence we still see the brown fumes. While,
it is unable to oxidised Cl-, thus is only able to protonate Cl- to give HCl.

KCl + H2SO4 → HCl + KHSO4

KBr + H2SO4 → HBr + KHSO4


2HBr + H2SO4 → Br2 + SO2 + 2H2O

KI + H2SO4 → HI + KHSO4
8HI + H2SO4 → 4I2 + H2S + 4H2O

Comments:
1) Do remember the trend of ease of oxidation. When a species is
more willing to be reduced, it is more difficult to be oxidised.

2) Ease of oxidation is not the same as thermal stability.

3) Do note that in these set of equations, in order to oxidise the halide


ions, they are first converted into acid halide first.

4) You need to remember the equation to show the oxidation of the


hydrogen halides. YOUR DATA BOOKLET IS UNABLE TO HELP YOU
WITH THIS ONE!

(b)(i) Na Br O
% mass 15.2 53.0 31.8
% mass/Ar 15.2/23 = 0.66 53/79.9 = 0.66 31.8/16 =1.98
Ratio 1 1 3

Formula of salt: NaBrO3

Comments:
For ionic compounds, their formula is an empirical formula. Hence, this
calculation would be sufficient.

Kwok YL 9
NOV2005 P3

(b)(ii) Let oxidation number of Br be x


(+1) + (x) + 3(-2) = 0
x–5=0
x = +5
Thus oxidation number of Br is +5.

Comments:
Oxidation number must have a positive or negative sign which precedes
a number.

(b)(iii) 3Cl2 + NaBr + 6NaOH → NaBrO3 + 6NaCl + 3H2O

Comments:
Workings:
Cl2 is passed into alkaline Br-. NaBrO3 is formed, hence Br- is oxidised
while Cl2 is reduced.

By writing the respective half equation:


Equation 1: Cl2 + 2e → 2Cl-
Equation 2: Br- +6OH- → BrO3- + 6e + 3H2O
(Note: Oxidation using OH- because it is in alkaline condition)

Equation 2 + (3 x equation 1) = answer.

N05/III/5 Or
5O (a) The ease of the thermal decomposition of Group II nitrates decrease
down the group.
M(NO3)2(s) ∆ MO(s) + 2NO2(g) + ½O2(g)

This is because the down the group, the M2+ ion gets larger and hence
it becomes less polarizing. Therefore, the larger NO3- becomes less
polarised by the cation. Hence, when the anion is less polarised, the
ease of decomposition to form the metal oxide decreases.

Comments:
There are three marks to this question and there are three components
to this question, 1) Describe, 2) Explain and 3) Equation.

Another reason for the ease of decomposition to decrease, would be


that the formation of MO is not as stable as we progress down the
group as cation ion size becomes larger and lattice energy decreases.

Hence, this results in the decomposition reaction to become less


exothermic. Therefore, the incentive for M(NO3)2 is decompose to the
corresponding MO decreases.

(b) MgCl2 (s) → Mg2+ (aq) + 2Cl- (aq)

MgCl is an ionic compound. Thus, MgCl2 dissolves in water to produce


the respective hydrated ions.

Mg, being a relative small cation with a relatively high charge, is


slightly polarising. It polarises a water molecule and causes the water
to dissociate, releasing H+ ion. Therefore, partial hydrolysis occurs
and hence MgCl2 dissolves in water to give a slightly acidic solution of

Kwok YL 10
NOV2005 P3

pH > 6.5.

The way SiCl4 reacts with water is different from how MgCl2 reacts with
water. This is because SiCl4 is a covalent compound and exists as a
simple discrete molecule. Si being a period 3 element has available d-
orbital to accept lone pair of electrons from water to cause hydrolysis.

Therefore, the hydrolysis of SiCl4 produces HCl to appear (as seen in


the equation below), and since SiCl4 undergoes full hydrolysis hence
creating a strongly acidic solution.

SiCl4 + 2H2O → SiO2 + 4HCl

Comments:
It is important to link the structure of the two different chloride and
account for the difference in observation when both react with water.

Some common misconception is to assume that SiCl4 is a giant


covalent structure (on the pretext that SiO2). This is not true. A giant
covalent structure of SiO2 would not be able to interact with water, and
hence if SiCl4 possess such a structure, it will not be able to undergo
hydrolysis in water.

Note that SiCl4 produces a more acidic solution because it undergoes


full hydrolysis.

(c)(i) Ba O
% mass 81.1 18.9
% mass/Ar 81.1/137 = 0.59 18.9/16 = 1.18
Ratio 1 1.18/0.59 = 2

Formula of the oxide: BaO2

Comments:
Please show by means of calculation to show the formula. Since, this
is an ionic compound obtaining formula by this means will be suffice.

(c)(ii) BaO2 + 2H2O → Ba(OH)2 + H2O2


A solution of Ba(OH)2 and H2O2 is obtained. This solution is acidified
before KI being added.

Since I- will be oxidised to I2 by the acidified solution, thus, the solution


contains an oxidising agent. Therefore, the oxidising agent is H2O2.
H2O2 + 2H+ + I- → 2H2O + I2

The acidification is done to enable reduction of H2O2 which works in an


acid medium. In addition, it is done to remove Ba(OH)2.

Comments:
Since BaO2 is added to water to give Ba(OH)2 and another compound.
You should write the equation and balance the elements. In the
identity of the other compound would be H2O2, which can act as either
an oxidising agent or reducing agent. Since adding KI produces I2, it
implies that H2O2 functions as an oxidising agent in this case.

Kwok YL 11
NOV2005 P3

N2005/III/8 either
8E (a)(i) Cracking is a process where a larger hydrocarbon is broken into
smaller fragments: Breaking of a larger alkane molecule into smaller
alkane or alkene fragments.

Comments:
Please remember such definition questions. Other definition questions
include “relative atomic, isotopic, molecular mass” and “strong (or
weak) acid”. You might be call to define or explain jargon (chemistry
terms) which you have taken for granted its meaning.

(a)(ii) Heat and catalyst such as Pt is being used.

Comments:

(a)(iii) C10H22 → C2H4 + C8H18

Comments:
You need to show a smaller molecule is being produced from the
larger molecule. Therefore, ensure that the number of C and H is
balanced.

(a)(iv) Large molecules in crude oil can be converted to more usefully smaller
molecules such as ethene, which can be used to produce polymer and
various other useful products.

Comments:
Usually students tend to forget about the purpose of a reaction, hence
they will face difficulties in answering this question. Therefore, it is
quite important to remember a few reactions which are applicable to
industries, e.g. cracking, Haber Process, Contact Process.

(b) Electrophilc addition


d+ d-
Br Br -
Br Br
Br Br
H H fast
slow + H C C H
C C H C C H

H H H H
H H

Comments:
This is an electrophilic addition reaction. The electrophile is the d+ on
Br-Br molecule. This d+ is generated as the Br2 molecules moves
towards the double bond. Once the d+ is generated, the π electrons
would be attracted to Br with the d+, therefore causing the flow of
electrons pairs as denoted by the curly arrows.

It is important to take note of the partial charges. They are crucial for
the electrophilic addition reaction.

Besides showing the carbocation as the intermediate (product of the


slow step), you could also show the bromonium ion.

Kwok YL 12
NOV2005 P3

(c)(i) H OH

H3C C C CH3

CH3 CH3

Comments:
The reagents used are similar to saying an alkene into steam and
H3PO4 at 300 oC and 70 atm. Therefore, it is the formation of an
alcohol.

To form a diol, you would have to use cold, dilute alkaline KMnO4.

(c)(ii) H H H H O
O

C C C C C C
HO OH
H H H H

Comments:
The reagent used for this question is that for vigorous oxidation. Thus,
there is a cleavage of the C=C. Since, the alkene fragments are both
in the generic form of RHC=, where R = rest of the molecule, the
double bond would be cleaved to form a carboxylic acid (-COOH).

Since both alkene fragment’s R is linked (we are dealing with a


cyclohexene), therefore, we will only obtain one product.

This is a very useful reaction to remember. Not only you have only one
product formed, your final product contains the same number of carbon
atoms as your reactants.

N2005/III/8 or
8O (a)(i) PBr3

Comments:
Nucleophilic substitution reaction has occurred.

(a)(ii) K2Cr2O7, heat and distill.

Comments:
Do not use K2Cr2O7 and heat under reflux. This is because the alcohol
will be fully oxidsed to give carboxylic acid. (Note: aldehyde can be
oxidised to form carboxylic acids).

Hence, slight warming would be good enough and distillation will help
to take out the aldehyde.

Note: Aldehyde has a lower boiling point than alcohol. Hence, using
distillation will enable the aldehyde to be removed from an aqueous
solution containing the excess alcohol and oxidising agent.

Kwok YL 13
NOV2005 P3

(a)(iii) Concentrated H2SO4, 170 oC.

Comments:
Elimination reaction has occurred.

(b) Nucleophilic substitution

H H H
d+ d- d+ d-

NC xx
H C d-
Br NC C Br d-
d+
C H
+ Br xx
NC
H3C CH3
H CH3

transition state

Comments:
Remember than in the cyanide ion, the lone pair of electron lies on the
carbon atom. In addition, the charge on the ion is also on the carbon
atom.

Ensure that the charges are properly shown. Include the partial
charges as they are required for nucleophilic substitution.

(c)(i) H3C H

C C
H3C H

Comments:
Using ethanolic OH-, we will obtain the alkene. The usage of aqueous
OH-, we will have nucleophilic substitution of Br for OH.

Extra information:
• Using aqueous hydroxide will only produce the alcohol.
• Using ethanolic hydroxide will generally produce the alkene but you
may get the alcohol or even a nucleophilic substitution of Br with the
solvent (ethanol).

The reason to why aqueous medium only produce one product is


because elimination reaction requires a much higher Ea and hence
doesn’t occur, we use OH- in ethanol because that is more reactive
that OH- in water.

Having said all that the main point of questions like (c)(i), we actually
state the MAIN product. Therefore, the formation of alkene is the
answer.

Kwok YL 14
NOV2005 P3

(c)(ii) H H O

H3C C CN H3C C C OCH2CH3

CH3 K CH3 L

Comments:
In the second step, ethanol and concentrated H2SO4 is added.
Therefore, this is an esterification step.

(c)(iii) H H

H3CH2CHN C C NHCH2CH3

H H
M

Comments:
There are two C – Br bonds. Both would undergo nucleophilic
substitution with CH3CH2NH2.

Since excess CH3CH3NH2 is used, it will ensure that the two Br are
being substituted. In addition, excess amines would prevent multiple
substitutions on N (thus prevent the formation of 2o and 3o amines).

Note that amines are more nucleophilic than NH3 because of alkyl
group which are electron donating. Hence, 2o and 3o would be even
more nucleophilic.

Kwok YL 15

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