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PAPER 2 – STRUCTURED QUESTIONS

Question 1
a)
i)

H H
xx xx
H O C C O H
xx xx
H H
Comments:
1. Ensure that the O-H bonds are shown. Becareful when you draw the display formula
of the following types of organic compounds: (A) Alcohol, (B) Carboxylic Acid, (C)
Amines and (D) Amides.
2. Do ensure that the lone pairs are drawn. If the question asked for it, please give as
mark will be allocated. Usually, we do not include the lone pairs when we draw the
display formula.

ii)

H Correct O-H bond

xx Lone pair in correct place in H-Bond
R C O H Use of dipoles at coordination
xx
H H
H O C R
δ+ δ−
H
Comments:
1. This is a straight-forward diagram with numerous details to take note of. When
including the partial charges, they must come from a pair of atoms that is linked together
by a bond. Do NOT show the partial charges of two atoms which are not linked together
by a bond.

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b)
i) C2H4
Comments:
1. Do not be surprised that the question states a gas. Ethene with just two carbons and 4
hydrogen atoms is a non-polar molecule. It has only id-id interactions as IMF. Thus, it
should not be surprising that it exists as a gas in room temperature.

ii) KMnO4 is decolourised

c) Phenol ; Alcohol; Amine;

Classification of functional groups e.g. Secondary alcohol / primary amine
Comments
1. This is a 4 marks question. Each type of functional group is worth one mark. Hence,
we need to be specific and talk about 1o, 2o or 3o to get the 4th mark.
2. Using hydroxyl as functional group is inappropriate. This is because hydroxyl refers
to alcohols and phenols; these compounds have different reactions.

d) (Structures are not drawn)

i) All 3 H atoms on the phenyl substituent are replaced by Br
Comments:
1. “Suitable” solvent may be deemed ambiguous. Since Br2(aq) would result in multiple
substitutions while Br2 (in CCl4) would result in mono-substitution. However, the
question gives us EXCESS Br2. This implies that regardless of the solvent used, multiple
substitutions will happen.

ii) Both phenolic –OH groups become –O-

Comments:
1. A gentle reminder – alcohols do not react with NaOH. They are pretty much neutral
in nature.

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iii) Side-chain –CHOH– becomes –CO–

Comments:
1. If you have protonated the N in –NH–CH3, that is a good practice but it is not given a
mark in this question. – If this part has an additional mark, you will definitely need to
protonate the N.
2. Take note that K2Cr2O7/H+ does not oxidize the side chain of benzene.

iv) Protonation of N in –NHCH3

Extra notes for question 1:

1. Avoid writing in pencil. Especially when drawing the structure of the molecules
2. When a blatantly wrong structure is drawn, all the marks will be removed
3. Remember that you shouldn’t make a mistake whereby there is one night or one
wrong. Because benefit of doubt is not given

Question 2

a)
i) Ksp = [Ag+] [Br-]
ii) [Ag+] = [Br-] [AgBr]
Ksp = 7.1 x 10-7 x 7.1 x 10-7 = 5.041 x 10-13
Gives Ksp = 5.0 x 10-13 (to 1 d.p.)
Comments
1. The question wants the numerical answer to be in one d.p. Hence you will need to do
that for the entire question.

b)
i) ΔGpptӨ = -55314.2262 J mol-1 = -55.3 kJ mol-1
Comments:
1. It is very important to include the appropriate signs in the values of ∆G, ∆H and ∆S.

ii) ΔGpptӨ = ΔHpptӨ - T ΔSpptӨ => ΔSpptӨ = -10.7 / 298 = -35.9 J mol-1 K-1
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iii) Entropy decreases

Ordered solid lattice formed
Comments:
1. You will need to use one of the following to explain the sign on ∆S. (A) Change in
temperature, (B) Change in phase, (C) Change in the number of gas particles after a
chemical reaction, (D) Mixing occurs.
2. In this situation, it is due to formation of the precipitate, and the reaction shows a
change in phase, from an aqueous state to a solid state. This results in the system to
become more ordered and hence entropy decreases.

c) ΔGpptӨ = + 14.81 (use formula)

= +14.8 J mol-1
Precipitation will not occur.
AgCl is soluble.
Comments:
1. A positive ∆G tells us that the reaction which we are considering is not feasible.
Since, the reaction we are considering is the precipitation of AgCl, when this ∆G > 0, this
will implies that the precipitation reaction is not feasible. – Hence, does not occur.
2. If precipitation does not take place, this implies that the AgCl is soluble.

Extra notes for question 2:

1. Just stating ΔS > 0, saying entropy increases is good enough
2. When they said reaction is feasible when ΔG > 0 is a contradiction. Hence
penalty is given
3. 1 mark penalty for d.p. error

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Question 3
CO2H

CH3
CHCO2H

a) CH3 CO2H

b)
i) EcellӨ = +1.52 – (+0.70V) = + 0.82 V

ii) 5 C6H6O2 + 2 MnO4- + 6 H+ Æ 5 C6H4O2 + 2 Mn2+ + 8H2O

iii) H2 or SO2
EӨ is less positive than +0.7 V
Comments:
1. For a redox reaction to be spontaneous, EӨcell > 0. This value can be calculated using
the formula: EӨcell = EӨreduction half-cell - EӨoxidation half-cell.. - Since EӨreduction half-cell. = +0.70V,
for the EӨcell > 0; the substance’s oxidised form’s reduction potential (or electrode
potential) must be smaller than +0.70V, so that the substance can be oxidised by quinone.

c) NaBH4 or LiAlH4
Comments:
1. H2 or Catalyst is not suitable.

d)
i) 2,4 DNPH (Spell in full)
Red / orange precipitate
ii) Na
Gas produced creates a pop sound when a burning splint is passed into it. (H2
produced)
iii) Br2
Br2 decolourised or white precipitate formed.

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Extra notes for question 3:

Stating Ecell > 0 to explain that the reactiontakes place would be good even if calculation
is not shown, except for difficult questions

Question 4
a) Cu: 1s22s22p63s23p63d104s1 Cu2+: 1s22s22p63s23p63d9

b)
i) B = Ag(NH3)2Cl
Comment:
1. Giving AgCl is insufficient and giving Ag(NH3)2+ is also not sufficient.
2. Since compound B is formed upon the addition of NH3 to the white precipitate, this
implies that both cation and anion are present in B. In this case, B’s cation is a complex
ion.

ii) CuCl2 contains [Cu(H2O)6]2+

C contains [Cu(NH3)4(H2O)2]2+ (actual correct answer) but allow [Cu(NH3)4]2+

c)
i) D: CuCl2 + 2HCl Æ H2CuCl2
E: CuCl2 + Cu + 2HCl Æ 2HCuCl2
Comments:
1. The clue is found in the question. 2 mole of HCl is required in the reaction and hence
in the balanced equation we should see that.

ii) D: [CuCl4]2- E: [CuCl2]-

iii) Ligand exchange
Comment:
1. Using the answer given in (b) (ii) will help you obtain the answer. In aqueous
solution Cu2+ exists as a complex ion and it exists as [Cu(H2O)6]2+.

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iv) D = tetrahedral (or square planar)

Comments:
1. Although you do need to know the rules to decide where a complex ion is tetrahedral
or square planar. Usually, Cu complexes with 4 ligands exist as tetrahedral.

v) +1
Comment:
1. Cu (I) complex is formed.

d)
i) Reduction / Redox ii) CuCl

e)
i) Cu : F : K = 1 : 6 : 3
CuF6K3 or K3CuF6
ii) +3

f)
i) Cu(I) has no empty / half-filled d-orbitals
no d-d transition possible
Comments:
1. The above answer is the main points to account for why Cu+ is colourless.

ii) Cu(III) is 3d5 and has empty d orbital

There is also available electrons at the d orbital with lower energy hence, d-d
transition is possible

Extra notes for Question 4:

1. Sometimes we need the full answer. It depends on the question
2. When the empirical formula is given, the order where the elements are placed is
not crucial.

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