| Date | May 2017 | Marks available | 2 | Reference code | 17M.3.hl.TZ1.25 |
| Level | HL | Paper | 3 | Time zone | TZ1 |
| Command term | Suggest | Question number | 25 | Adapted from | N/A |
Question
Solubility plays an important role in the bioavailability of drugs in the body.
Suggest why aspirin is slightly soluble in water. Refer to section 37 of the data booklet.
A student prepares aspirin from salicylic acid in the laboratory, extracts it from the reaction mixture, ensures the sample is dry and determines its melting point.
Suggest why the melting point of the student’s sample is lower and not sharp compared to that of pure aspirin.
Organic molecules can be characterized using infrared (IR) spectroscopy.
Compare and contrast the infrared peaks above 1500 cm−1 in pure samples of aspirin and salicylic acid using section 26 of the data booklet.
Some mild analgesics contain a solid mixture of acidic aspirin and a non-acidic organic chemical of similar polarity to asprin.
Discuss how acid-base properties and the process of solvent extraction can be used to separate aspirin from the mixture.
The pharmaceutical industry is one of the largest producers of waste solvents.
State a green solution to the problem of organic solvent waste.
Markscheme
presence of «large» benzene/arene ring AND non-polar/hydrophobic
OR
presence of «large» benzene/arene ring AND cannot form H-bond with water
contain COOH/carboxyl/–OH/hydroxyl «and ester group» AND polar/hydrophilic
OR
contain COOH/carboxyl/–OH/hydroxyl «and ester group» AND can form H-bonds with water
Accept “phenyl” for “benzene ring”.
Accept "carboxylic acid" for "carboxyl".
Do not accept "alcohol" for "hydroxyl".
[2 marks]
«student’s» sample impure
lattice disrupted/not uniform «due to presence of impurities»
OR
fewer interparticle/intermolecular forces «due to presence of impurities»
Accept converse arguments.
[2 marks]
One similarity:
peak at 2500–3000 «cm–1»/peak due to O–H/hydroxyl in carboxylic acids
OR
peak at 1700–1750 «cm–1»/peak due to C=O/carbonyl
OR
peak at 2850–3090 «cm–1»/peak due to C–H of arene
One difference:
peak at 3200–3600 «cm–1» in salicylic acid/ peak due to O–H in phenol in salicylic acid
OR
«two» peaks at 1700–1750 «cm–1» in aspirin AND one peak «in the same area» in salicylic acid
Accept “peak at 1600 cm–1 for arene/benzene ring” – not in the data booklet.
Accept “2500–3600 cm–1 «overlapping absorptions of two O–H» in salicylic acid”.
Accept “stronger/broader/split peak at 1700–1750 cm–1 in aspirin”.
[2 marks]
dissolve compounds in an organic solvent
add NaOH(aq)/OH–(aq) «to the mixture» to convert aspirin to its water soluble salt
separate the two «immiscible» layers
convert salt «in aqueous layer» back to aspirin by reacting with acid/H+
«evaporate solvents and dry»
Accept organic solvents immiscible with water such as hexane, ethyl ethanoate, butyl acetate.
Accept any other base.
Need explanation for mark.
[3 marks]
«use of» alternative solvents such as supercritical/liquid CO2
OR
use of water «as solvent»
OR
solvent-free reactions «for example, polymerization of propene»
OR
solid-state chemistry
OR
recycle «waste» solvents
OR
catalysis that leads to better/higher yield
OR
reducing number of steps
Do not accept political/regulatory solutions.
“catalysis” not sufficient for mark.
[1 mark]
Examiners report
Syllabus sections
-
18M.3.sl.TZ1.13c.iv:
State how penicillins may be modified to increase their effectiveness.
-
18M.3.sl.TZ2.16a.ii:
State how penicillins may be modified to increase their effectiveness.
- 17N.3.hl.TZ0.22b: Describe how mild analgesics function.
- 17N.3.sl.TZ0.17a: Aspirin is a mild analgesic derived from salicylic acid found in willow bark. Describe how...
-
17M.3.sl.TZ2.15b.i:
State how aspirin can be converted to water-soluble aspirin.
- 16N.3.sl.TZ0.18d: State why aspirin is described as a mild analgesic with reference to its site of action.
-
17M.3.sl.TZ1.19c:
A student prepares aspirin from salicylic acid in the laboratory, extracts it from the reaction mixture, ensures the sample is dry and determines its melting point.
Suggest why the melting point of the student’s sample is lower and not sharp compared to that of pure aspirin.
-
17M.3.hl.TZ1.25c:
Organic molecules can be characterized using infrared (IR) spectroscopy.
Compare and contrast the infrared peaks above 1500 cm−1 in pure samples of aspirin and salicylic acid using section 26 of the data booklet.
-
20N.3.sl.TZ0.11a:
Deduce the structural formula of the by-product of this reaction.
-
19M.3.sl.TZ2.15a:
Predict one absorption band present in an infrared (IR) spectrum of aspirin, using section 26 of the data booklet.
- 18N.3.sl.TZ0.12a: State the internal bond angles in the β-lactam ring and the expected bond angles for the same...
- 18N.3.sl.TZ0.12d: State how the structure of penicillin can be changed to combat this effect.
- 18N.3.sl.TZ0.12e: Suggest why human cells are not affected by penicillin.
- 18N.3.hl.TZ0.16d: Suggest why human cells are not affected by penicillin.
- 18N.3.hl.TZ0.16a: State the internal bond angles in the b-lactam ring and the expected bond angles in sp2 and...
- 18N.3.hl.TZ0.16c: State how the structure of penicillin can be modified to combat the effect of...
- 18N.3.hl.TZ0.16b: Explain how the open β-lactam ring kills bacteria.
- 18N.3.sl.TZ0.12b: Explain how the open β-lactam ring kills bacteria.
-
18M.3.sl.TZ2.16c:
Explain why aspirin is not stored in a hot, humid location.
- 17N.3.sl.TZ0.21: Molecules of antibiotics often contain a beta-lactam ring. Explain the importance of the...
-
19M.3.sl.TZ1.15b(i):
The widespread use of penicillin and its derivatives has led to the appearance of resistant S. aureus strains.
Outline how these bacteria inactivate the antibiotics.
-
19M.3.sl.TZ1.15b(ii):
Outline how the structure of penicillin has been modified to overcome this resistance.
-
16N.3.sl.TZ0.16a:
(i) Outline what is meant by the term “ring strain”.
(ii) On the diagram above, label with asterisk/s (*) the carbon atom/s that experience ring strain.
-
17M.3.sl.TZ1.19b:
Formulate an equation for the conversion of aspirin to a more water soluble derivative.
-
19M.3.sl.TZ2.15d:
State why aspirin should not be taken with alcohol.
-
19M.3.sl.TZ1.15a:
Identify the feature in penicillin responsible for its antibiotic activity.
-
17M.3.hl.TZ2.20a.iv:
State two techniques, other than IR spectroscopy, which could be used to confirm the identity of aspirin.
-
18M.3.sl.TZ1.13c.i:
Compare and contrast the IR spectrum of aspirin with that of salicylic acid, using section 26 of the data booklet.
- 19N.3.hl.TZ0.25a: Explain how the beta-lactam ring is responsible for the antibiotic properties of penicillin....
-
18M.3.sl.TZ2.16a.i:
Describe how penicillin combats bacterial infections.
- 19N.3.sl.TZ0.17a: Suggest one reactant used to prepare aspirin from salicylic acid.
-
19M.3.sl.TZ2.15b(ii):
Determine the percentage purity of the synthesized aspirin.
-
17M.3.sl.TZ1.19d:
Organic molecules can be characterized using infrared (IR) spectroscopy.
Compare and contrast the infrared peaks above 1500 cm−1 in pure samples of aspirin and salicylic acid using section 26 of the data booklet.
-
19M.3.hl.TZ1.19a:
Unreacted salicylic acid may be present as an impurity in aspirin and can be detected in the infrared (IR) spectrum.
Name the functional group and identify the absorption band that diff erentiates salicylic acid from aspirin. Use section 26 of the data booklet.
Name:
Absorption band:
-
19M.3.sl.TZ1.14:
Aspirin can be obtained from salicylic acid.
Unreacted salicylic acid may be present as an impurity in aspirin and can be detected in the infrared (IR) spectrum.
Name the functional group and identify the absorption band that differentiates salicylic acid from aspirin. Use section 26 of the data booklet.
Name:
Absorption band:
-
18M.3.sl.TZ1.13b.ii:
Outline how the bioavailability of aspirin may be increased.
-
17M.3.hl.TZ1.25a:
Suggest why aspirin is slightly soluble in water. Refer to section 37 of the data booklet.
-
17M.3.sl.TZ2.15a.iii:
State two techniques which could be used to confirm the identity of aspirin.
- 19N.3.sl.TZ0.18c: The discovery of penicillins contributed to the development of antibiotics. Explain how the...
-
19M.3.hl.TZ1.20b(i):
The widespread use of penicillin and its derivatives has led to the appearance of resistant S. aureus strains.
Outline how these bacteria inactivate the antibiotics.
-
18M.3.sl.TZ2.16b:
State the type of reaction used to synthesize aspirin from salicylic acid.
-
19M.3.hl.TZ2.22d:
State why aspirin should not be taken with alcohol.
-
19M.3.hl.TZ2.22b(ii):
Determine the percentage purity of the synthesized aspirin.
-
19M.3.hl.TZ2.22c:
Outline how aspirin can be chemically modified to increase its solubility in water.
-
19M.3.hl.TZ1.20b(ii):
Outline how the structure of penicillin has been modified to overcome this resistance.
-
19M.3.sl.TZ2.15b(i):
Determine the mass of aspirin which reacted with 16.25 cm3 of 0.100 mol dm−3 NaOH solution.
-
19M.3.hl.TZ1.20a:
Identify the feature in penicillin responsible for its antibiotic activity.
-
18M.3.sl.TZ1.13c.ii:
Describe how penicillin combats bacterial infections.
-
19M.3.hl.TZ2.22b(i):
Determine the mass of aspirin which reacted with 16.25 cm3 of 0.100 mol dm−3 NaOH solution.
-
18M.3.sl.TZ1.13a:
Aspirin is often taken to reduce pain, swelling or fever. State one other use of aspirin.
-
19M.3.hl.TZ2.22a:
Predict one absorption band present in an infrared (IR) spectrum of aspirin, using section 26 of the data booklet.
-
19N.3.sl.TZ0.17b:
Aspirin, C6H4(OCOCH3)COOH, is only slightly soluble in water.
Outline, including an equation, how aspirin can be made more water-soluble. Use section 37 in the data booklet.
-
16N.3.sl.TZ0.16b:
(i) Some antibiotic-resistant bacteria produce a beta-lactamase enzyme which destroys penicillin activity. Suggest how adding clavulanic acid to penicillin enables the antibiotic to retain its activity.
(ii) Populations of antibiotic-resistant bacteria have increased significantly over the last 60 years. Outline why antibiotics such as penicillin should not be prescribed to people suffering from a viral infection.
-
19M.3.sl.TZ2.15c:
Outline how aspirin can be chemically modified to increase its solubility in water.
- 20N.3.hl.TZ0.15b: Aspirin crystals are rinsed with water after recrystallization to remove impurities.Suggest...
-
20N.3.hl.TZ0.15c:
The solubility of aspirin is increased by converting it to an ionic form. Draw the structure of the ionic form of aspirin.
-
17M.3.sl.TZ1.19a:
Suggest why aspirin is slightly soluble in water. Refer to section 37 of the data booklet.
- 20N.3.sl.TZ0.11b: Aspirin crystals are rinsed with water after recrystallization to remove impurities.Suggest...
-
20N.3.hl.TZ0.15a:
Deduce the structural formula of the by-product of this reaction.
-
20N.3.hl.TZ0.19b(ii):
Explain, with reference to the action of penicillin, why new penicillins with different side-chains need to be produced.
-
20N.3.hl.TZ0.15e:
Explain how IR spectroscopy can be used to distinguish aspirin from salicylic acid.
- 20N.3.sl.TZ0.14b(i): Circle the side-chain in penicillin on the structure below.
-
20N.3.sl.TZ0.14b(ii):
Explain, with reference to the action of penicillin, why new penicillins with different side-chains need to be produced.
- 20N.3.hl.TZ0.19b(i): Circle the side-chain in penicillin on the structure below.
-
20N.3.sl.TZ0.11c:
The solubility of aspirin is increased by converting it to an ionic form. Draw the structure of the ionic form of aspirin.
