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Date November 2013 Marks available 1 Reference code 13N.3.hl.TZ0.14
Level HL Paper 3 Time zone TZ0
Command term State Question number 14 Adapted from N/A

Question

A modern method for accurately determining ethanol concentrations in the breath is based on the infrared (IR) spectrum of the molecule.

N13/4/CHEMI/HP3/ENG/TZ0/14

Use Table 17 of the Data Booklet to identify the wavenumber range used in the determination.

[1]
a.i.

State why the absorption in the range 3200 to 3600 \({\text{c}}{{\text{m}}^{ - 1}}\) is not used.

[1]
a.ii.

The concentration of ethanol is determined by passing IR radiation through a breath sample. Outline how the transmittance of IR radiation changes when increased levels of ethanol are present.

[1]
b.

Markscheme

2850 – 3100 \({\text{(c}}{{\text{m}}^{ - 1}}{\text{)}}\);

a.i.

(OH absorption present) in water/air/water vapour;

a.ii.

transmittance decreases / absorbance increasing (with increasing concentration);

No mark for: transmittance/absorbance changes.

b.

Examiners report

Option D was a popular option. The identification of the wavenumber range used in the determination of ethanol lead to many correct answers. However, why the absorption range 3200-3600 \({\text{c}}{{\text{m}}^{ - 1}}\) is not used still eludes a substantial number of candidates. How the transmission of IR radiation changes with increased levels of ethanol was not answered well, showing a poor understanding of transmittance. The question on the mild analgesic was not very well except for being able to identify the amide group in the molecules in question. The physiological effect of the drug as well as the reason for some drugs being less effective when taken orally was both very well answered. The ‘mix and split’ approach to combinatorial chemistry was generally not done well with answers that were weak showing shallow understanding.

The two structural features found in the sympathomimetic drugs were mostly correctly identified. Although many students were able to identify two chiral centers in the two structures given, not as many could identify the three needed for the mark. In the preferred method for the synthesis of optically active drugs, where many scored full marks but the difficulty of separating enantiomers due to their similar physical properties was the least popular explanation given. Surprisingly, the suggestion for increasing the aqueous solubility of an alkaline drug by adding an acid or converting it to its salt was done poorly showing a lack of understanding of acid-base chemistry and bonding.

In one argument for and one against the legalization of cannabis, while many candidates scored at least one mark out of two, some journalistic answers were seen. Description of the bonding changes that occur when the anti-cancer drug cisplatin attaches to the DNA chain was typically not well answered questions with many candidates being able to provide only one of the two ideas, usually the missing one was that \({\text{C}}{{\text{l}}^ - }\) leave \({\text{Pt/P}}{{\text{t}}^{2 + }}\). Why the trans-cisplatin is ineffective in the treatment of cancer elicited fewer correct answers than expected. Question 18 was not on AIDS per se but rather on why viral infections are more difficult to treat than bacterial infections. A significant number of students scored part marks thus illustrating shallow understanding and deserves further attention in class. Very often marks were lost due to incomplete arguments.

a.i.

Option D was a popular option. The identification of the wavenumber range used in the determination of ethanol lead to many correct answers. However, why the absorption range 3200-3600 \({\text{c}}{{\text{m}}^{ - 1}}\) is not used still eludes a substantial number of candidates. How the transmission of IR radiation changes with increased levels of ethanol was not answered well, showing a poor understanding of transmittance. The question on the mild analgesic was not very well except for being able to identify the amide group in the molecules in question. The physiological effect of the drug as well as the reason for some drugs being less effective when taken orally was both very well answered. The ‘mix and split’ approach to combinatorial chemistry was generally not done well with answers that were weak showing shallow understanding.

The two structural features found in the sympathomimetic drugs were mostly correctly identified. Although many students were able to identify two chiral centers in the two structures given, not as many could identify the three needed for the mark. In the preferred method for the synthesis of optically active drugs, where many scored full marks but the difficulty of separating enantiomers due to their similar physical properties was the least popular explanation given. Surprisingly, the suggestion for increasing the aqueous solubility of an alkaline drug by adding an acid or converting it to its salt was done poorly showing a lack of understanding of acid-base chemistry and bonding.

In one argument for and one against the legalization of cannabis, while many candidates scored at least one mark out of two, some journalistic answers were seen. Description of the bonding changes that occur when the anti-cancer drug cisplatin attaches to the DNA chain was typically not well answered questions with many candidates being able to provide only one of the two ideas, usually the missing one was that \({\text{C}}{{\text{l}}^ - }\) leave \({\text{Pt/P}}{{\text{t}}^{2 + }}\). Why the trans-cisplatin is ineffective in the treatment of cancer elicited fewer correct answers than expected. Question 18 was not on AIDS per se but rather on why viral infections are more difficult to treat than bacterial infections. A significant number of students scored part marks thus illustrating shallow understanding and deserves further attention in class. Very often marks were lost due to incomplete arguments.

a.ii.

Option D was a popular option. The identification of the wavenumber range used in the determination of ethanol lead to many correct answers. However, why the absorption range 3200-3600 \({\text{c}}{{\text{m}}^{ - 1}}\) is not used still eludes a substantial number of candidates. How the transmission of IR radiation changes with increased levels of ethanol was not answered well, showing a poor understanding of transmittance. The question on the mild analgesic was not very well except for being able to identify the amide group in the molecules in question. The physiological effect of the drug as well as the reason for some drugs being less effective when taken orally was both very well answered. The ‘mix and split’ approach to combinatorial chemistry was generally not done well with answers that were weak showing shallow understanding.

The two structural features found in the sympathomimetic drugs were mostly correctly identified. Although many students were able to identify two chiral centers in the two structures given, not as many could identify the three needed for the mark. In the preferred method for the synthesis of optically active drugs, where many scored full marks but the difficulty of separating enantiomers due to their similar physical properties was the least popular explanation given. Surprisingly, the suggestion for increasing the aqueous solubility of an alkaline drug by adding an acid or converting it to its salt was done poorly showing a lack of understanding of acid-base chemistry and bonding.

In one argument for and one against the legalization of cannabis, while many candidates scored at least one mark out of two, some journalistic answers were seen. Description of the bonding changes that occur when the anti-cancer drug cisplatin attaches to the DNA chain was typically not well answered questions with many candidates being able to provide only one of the two ideas, usually the missing one was that \({\text{C}}{{\text{l}}^ - }\) leave \({\text{Pt/P}}{{\text{t}}^{2 + }}\). Why the trans-cisplatin is ineffective in the treatment of cancer elicited fewer correct answers than expected. Question 18 was not on AIDS per se but rather on why viral infections are more difficult to treat than bacterial infections. A significant number of students scored part marks thus illustrating shallow understanding and deserves further attention in class. Very often marks were lost due to incomplete arguments.

b.

Syllabus sections

Options » D: Medicinal chemistry » D.9 Drug detection and analysis (HL only)
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