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

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 tetrahedral

H3PO4 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,

n (H3PO4 ) = n (P) =

0.558 = 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.

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.

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.

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

Report and Analysis of MIChO Selection Structured Problems 2012 The score and penalty of the candidates are shown in the table below.
Name Kee Li En Foo Ming Jeat Ong Chern Juin Muhammad Izzuddin Faiz Cheong See Mun Wong Siew Fern Muhammad Farhan b Mokhtar Taufiq Hamidi Khairom Muslihin Shazard Amani Ashwani Amani bt Ahmad Mokhtar Chong Zhi Juan Nurul Shahidah Yeo Wen Lin Muhammad Fkhruddin Ghazali Wan Nabilah Krishantini Mohd Izzat Nur Azah Muhamad Zubair Nurfarihah Rasyidah bt Rehir Muhamad Ammar Sofieya Farhana Wan Enis Farahaini Nur Fatihah Tengku Ainul Asma' Muhammad Farhan Mohd Ali Noor Hanisah Ariwibawa Kasmani Ahmad Zuhayri Abdul Karim Institution KMNS Chong Hwa Independent Kolej Tuanku Jaafar (AS Level) KMB SMJK Chan Wa KMB KMB KMB PASUM PASUM PASUM PASUM KMB PASUM KMB KMB KMB KMB KMB KMB KMB KMB PASUM KMB KMB ? PASUM SMKA Baling KMB PASUM PASUM KMB KMB Score Penalty 22 1 17 4 3 15 13 11 2 11 4 10 3 10 4 10 4 8 1 5 6 2 6 2 5 1 5 2 5 3 4 1 4 1 4 2 3 3 1 2 2 2 2 1 2 1 2 1 1 1 0 0 0 0