Report and Analysis of MIChO

Selection Structured Problems

Version 2.0 (June 4, 2012)

Prepared by

Yau Ching Koon

Participated in IChO 2006
 Report and Analysis of MIChO Selection Structured Problems
2012
The marks of the structured problem can be typically breakdown into 13 (inorganic and
analytical), 14 (physical), and 11 (organic).

Part (a)

Only three candidates have correctly drawn the structure of phosphorus molecule. The
Lewis structure of P4 is technically harder than conventional molecules because it
requires a three dimensional visualization of the bonding.

Part (b)

Only eight candidates are able to determine the oxides of phosphorus. Many candidates
does not know that phosphorus has two common oxidation state, i.e. phosphorus(III)
and phosphorus(V). For those eight who knew, half of them wrote the empirical
formula of the oxide P2O3 and P2O5 respectively where a penalty is given. The oxides of
phosphorus are P4O6 and P4O10 respectively.

P4O6 P4O10

2
 Report and Analysis of MIChO Selection Structured Problems
2012

Part (c)

Only a few identified the dibasic acid as H3PO3 but failed to harvest the information
given except of one. As a result the structure of the dibasic acid drawn has three acidic
protons P(OH)3 and not HP(O)(OH)2. Many students know the tribasic acid. The
molecular geometry is tetrahedral for both and not tetrahedron which refers to a Platonic
solid.

H3PO3 H3PO4
tetrahedral tetrahedral

Part (d)

Many candidates could not appreciate the following simple stoichiometric relationship
between elemental phosphorus that is burnt and phosphoric acid formed after the oxide
is dissolved in water.

One mole of P (not one mole of phosphorus molecules) produced one mole of
H3PO4.

Therefore,

0.558
n (H3PO4 ) = n (P) = = 0.0180 mol
30.97

Finally, most candidates failed to express their final answer in 3 s.f. based on the 3 s.f. of
0.558 g. One penalty is given.

3
 Report and Analysis of MIChO Selection Structured Problems
2012
Part (e)

No marks will be deducted for using the wrong answer from (d) in this part. Most
students are able to this part but with two major common mistakes. (1) Some students
failed to interpret mmol as ‘millimole’ and have fatally assumed a typo in the problem
themselves causing their answer to differ by a factor of 1000. (2) Some students did not
read the question carefully. The problem asked for the extra volume of water that
should be added for the dilution but this instruction is not appreciated.

Part (f)

No candidates could answer this problem. Here, I shall just disclosed the answer as pH
= 2.33 and invite the interested ones to prove to themselves.

Part (g)

Only one candidate can draw the structure of the salt correctly. Maybe, the students are
underexposed to polyatomic ions (cations in particular) and knew only the monoatomic
ions such as Na+. This may lead to fear of writing rather unconventional structures or
ions such as the one shown below.

4
 Report and Analysis of MIChO Selection Structured Problems
2012
Part (h)

Only three candidates get the correct answer for this part. The candidates are required
to show a bimolecular nucleophilic substitution SN2 mechanism with proper arrows. An
indirect hint has been given, viz. “Phosphorus is in the same group as nitrogen,” where
a candidate is expected to compare the chemistry of phosphorus compounds (PPh3)
with nitrogen compounds (NH3 or NEt3). That comparison would enable one to
appreciate triphenylphosphine to act as either a weak base or a nucleophile. On a
survey conducted earlier, most candidates are not exposed to organic chemistry yet and
that may attribute to the poor performance.

Part (i)

Only two candidates specify the function of n-butyl lithium as a base.

5
 Report and Analysis of MIChO Selection Structured Problems
2012
Part (j)

No candidates are able to solve the entire synthesis but only two are able to properly
identify the first step as a Grignard reaction and used acetaldehyde / ethanal (X) to
construct the first portion of the required carbon framework.

It was rather unfortunate that the candidates could not link the Wittig reaction
introduced earlier in the problem to this synthesis problem. If they could, they would
have disconnected the double bond of the target molecule.

The two possibility of disconnection can be discriminated by PBr3 (information given)

where one would expect (G) to be the precursor (i.e. an alkyl halide) of the Wittig
reagent (H).

The rest of the total synthesis is available at Lawrence T. Scott et. al., Science 295, 1500
(2002). DOI: 10.1126/science.1068427

6
 Report and Analysis of MIChO Selection Structured Problems
2012
The score and penalty of the candidates are shown in the table below.

Name Institution Score Penalty

Kee Li En KMNS 22 1
Foo Ming Jeat Chong Hwa Independent 17 4
Ong Chern Juin Kolej Tuanku Jaafar (AS Level) 15 3
Muhammad Izzuddin Faiz KMB 13
Cheong See Mun SMJK Chan Wa 11 2
Wong Siew Fern KMB 11 4
Muhammad Farhan b Mokhtar KMB 10 3
Taufiq Hamidi KMB 10 4
Khairom Muslihin PASUM 10 4
Shazard Amani PASUM 8 1
Ashwani PASUM 5
Amani bt Ahmad Mokhtar PASUM 6 2
Chong Zhi Juan KMB 6 2
Nurul Shahidah PASUM 5 1
Yeo Wen Lin KMB 5 2
Muhammad Fkhruddin Ghazali KMB 5 3
Wan Nabilah KMB 4 1
Krishantini KMB 4 1
Mohd Izzat KMB 4 2
Nur Azah KMB 3
Muhamad Zubair KMB 3 1
Nurfarihah KMB 2
Rasyidah bt Rehir PASUM 2
Muhamad Ammar KMB 2
Sofieya Farhana KMB 2 1
Wan Enis Farahaini ? 2 1
Nur Fatihah PASUM 2 1
Tengku Ainul Asma' SMKA Baling 1
Muhammad Farhan Mohd Ali KMB 1
Noor Hanisah PASUM 0
Ariwibawa Kasmani PASUM 0
Ahmad Zuhayri KMB 0
Abdul Karim KMB 0