Mark scheme
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Examiner's comment
1a(i) Most candidates labelled some of the apparatus correctly and identified the reflux technique. A significant number showed water flowing in the wrong direction and ‘distillation’ was given as the name of the technique. The ‘condenser’ was sometimes labelled incorrectly, e.g. ‘condensation tube, ‘distillation tube’ and ‘water jacket’. Only just over half the candidates were given both marks. 1a(ii) Many diagrams were incomplete and it was comparatively rare for both of the two available marks to be given. Important labels were often missing. Some candidates drew diagrams of other techniques, such as distillation. Many responses were not credited with marks and this question was often omitted. Candidates need practice in recognising practical techniques and in drawing acceptable diagrams. 1b(i) Candidates were expected to explain the different boiling points of three amines. Most candidates linked increased branching with less surface contact between molecules, leading to weaker induced dipole interactions (London forces). Fewer candidates linked the decreasing boiling points to less energy being required to break the intermolecular bonds. The highest performing candidates recognised the large difference between the boiling points of the primary and tertiary amines. They then identified the cause: primary amines form hydrogen bonds but tertiary amines do not. This question was answered reasonably well with fewer candidates than in the past describing relative strengths of covalent bonds, a common misconception. 1(b)(ii) Most candidates rearranged the ideal gas equation correctly to make n the subject. They then substituted correct values for p, V, R and T into the equation, with correct unit conversions. Most candidates then calculated n correctly as 2.32 × 10–3 and combined this value with the mass of 0.202 g to derive the molecular formula as 87. Lower-attaining candidates often made an error in their conversion of cm3 into m3, by multiplying by 10–3 rather than 10–6. This error resulted in a value of n as 2.32 and the unrealistic molecular mass of 8.7 × 10–3, from which a molecular formula is impossible. Candidates in this position are advised to check back at the unit conversions in the working. Very few candidates did not convert 100ºC into 373 K. Candidates with the correct molecular formula of 87 usually suggested C5H13N as the molecular formula. A significant number quoted C5H11NH2. This response was not credited as it is not a ‘molecular’ formula. There are several possible structures of C5H13N with three 13C NMR peaks and any were credited. Error carried forward was applied from a different molecular mass for both the molecular formula and a structure. This emphasises the importance of working within calculation; credit will always be given for a correct method. Instead of using the ideal gas equation, some candidates used the molar gas constant at room temperature and pressure, 24.0 dm3, which gives a molecular mass of 67. This simplified approach could only gain the final 2 marks for this question: a molecular formula (with an error carried forward value of 67, e.g. C4H5N) and a structure of an amine with this molecular formula and 3 peaks in the 13C NMR spectrum. 1(c) Candidates were supplied with information about an unfamiliar reaction of an amino acid and asked to predict a possible equation. Many candidates suggested H2O as one product, being the difference in the formula of the amino acid and the C3H3NO cyclic organic product. Any cyclic structure of C3H3NO that met the bonding rules for C, H, N and O was credited. Examples included a 4-membered ring lactam and substituted cyclopropenes. A significant number of candidates showed an equation for the reaction of two molecules of the amino acid to form 2 H2O and a cyclic dipeptide. Although chemically feasible, the dipeptide could not be credited because the molecular formula was C3H3NO in the question. This error could have been avoided if the information in the question had been used.
Notes from the mark scheme and report
- water in at bottom and out at top AND condenser
- pear-shaped/round-bottom flask AND reflux
- DO NOT ALLOW conical flask, volumetric flask or beaker
Skills: PAG5 Synthesis of an organic liquid
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