IBDP Official Exam Material
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Topic 21: Measurement and Analysis
For HL students only
A. Boiling and melting points
1. [1 mark]
What information can be deduced about a compound through X-ray crystallography?
A. Boiling and melting points
B. Bond angles
C. Bonds that will break during fragmentation
D. Ionization energy
2. [1 mark]
Which organic compound has the 1H NMR shown?
A. Methanal
B. Ethanoic acid
C. Methyl ethanoate
D. Propanoic acid
3. [1 mark]
Which compound produces the following 1H NMR spectrum?
A. propanal
B. propanone
C. propane
D. methlypropane
4. [1 mark]
Which substance has the following 1H NMR spectrum?
A. Propane
B. Propanal
C. Butanoic acid
D. Ethyl ethanoate
5a. [3 marks]
A 4.406 g sample of a compound containing only C, H and O was burnt in excess oxygen. 8.802 g of CO2 and 3.604 g of H2O were produced.
Determine the empirical formula of the compound using section 6 of the data booklet.
5b. [1 mark]
Determine the molecular formula of this compound if its molar mass is 88.12 g mol−1. If you did not obtain an answer in (a) use CS, but this is not the correct answer.
5c. [3 marks]
The following spectrums show the Infrared spectra of propan-1-ol, propanal and propanoic acid.
Identify each compound from the spectra given, use absorptions from the range of 1700 cm−1 to 3500 cm−1. Explain the reason for your choice, referring to section 26 of the data booklet.
5d. [2 marks]
Predict the number of 1H NMR signals, and splitting pattern of the –CH3 seen for propanone (CH3COCH3) and propanal (CH3CH2CHO).
5e. [1 mark]
Predict the fragment that is responsible for a m/z of 31 in the mass spectrum of propan‑1‑ol. Use section 28 of the data booklet.
6. [1 mark]
Which compound produces the following 1H NMR spectrum?
A. Propane
B. Propanone
C. Propanal
D. 2,2-dimethylpropane
7. [1 mark]
What information can be deduced from the splitting pattern of 1H NMR signals?
A. total number of hydrogen atoms in a compound
B. number of hydrogen atoms on adjacent atom(s)
C. functional group on which hydrogen atoms are located
D. number of hydrogen atoms in a particular chemical environment
8. [1 mark]
Which compound with the molecular formula C4H8O has this high resolution H1 NMR?
A. but-3-en-2-ol, CH2=CHCHOHCH3
B. butanal, CH3CH2CH2CHO
C. butanone, CH3COCH2CH3
D. but-3-en-1-ol, CH2=CHCH2CH2OH
9. [1 mark]
Which is the 1H NMR spectrum of tetramethylsilane, TMS, (CH3)4Si?
10. [1 mark]
X-ray crystallography of a metal crystal produces a diffraction pattern of bright spots.
Using X-rays of wavelength 1.54 × 10−10 m, the first bright spots were produced at an angle θ of 22.3° from the centre.
Calculate the separation between planes of atoms in the lattice, in meters, using section 1 of the data booklet.
11. [1 mark]
Which can be identified using infrared (IR) spectroscopy?
A. functional groups
B. molar mass
C. 3-D configuration
D. bond angle
12a. [1 mark]
Benzoic acid, C6H5COOH, is another derivative of benzene.
Identify the wavenumber of one peak in the IR spectrum of benzoic acid, using section 26 of the data booklet.
12b. [1 mark]
Identify the spectroscopic technique that is used to measure the bond lengths in solid benzoic acid.
12c. [1 mark]
Outline one piece of physical evidence for the structure of the benzene ring.
13a. [1 mark]
The structures of morphine, diamorphine and codeine are given in section 37 of the data booklet.
Methadone is used to treat heroin addiction. 1H NMR spectroscopy can be used to study its structure.
Predict the number of different hydrogen environments in the molecule ignoring the benzene rings.
13b. [2 marks]
Predict the chemical shift and the splitting pattern seen for the hydrogens on the carbon atom circled in the diagram. Use section 27 of the data booklet.
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