OCR A Jun 2016 Paper 4 Q5

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5 A chemistry teacher carries out an experiment to synthesise 2-aminopropan-1-ol, CH3CH(NH2)CH2OH. 12 (a) The teacher asks a university chemistry department to test the 2-aminopropan-1-ol using proton NMR spectroscopy and mass spectrometry. (i) For the 1H NMR analysis, the sample was dissolved in D2O. Complete the table to predict the 1H NMR spectrum of CH3CH(NH2)CH2OH after dissolving in D2O. 1H NMR spectrum for CH3CH(NH2)CH2OH, dissolved in D2O Chemical shift,/ ppm Relative peak area Splitting pattern (ii) The mass spectrum for CH3CH(NH2)CH2OH is shown below. [3] 100 relative intensity 80 60 40 20 peak 2 peak 1 25 50 m / z 75 100OCR 2016<br />
 Give the formulae for the species responsible for peak 1 and peak 2 in the mass spectrum. 13 peak 1 peak 2 (b) The teacher synthesises 2-aminopropan-1-ol, CH3CH(NH2)CH2OH, from 2-chloropropan-1-ol, CH3CHCl CH2OH. [2] (i) State the reagents and conditions required for this synthesis.[1] (ii) The sample prepared by the teacher from 2-chloropropan-1-ol is not pure. It also contains compound D. Compound D has a molecular formula of C6H15NO2. Suggest the structure of compound D. Compound D [1]OCR 2016 Turn over<br />
 (c) In a separate experiment, the chemistry teacher prepares compound E from 2-aminopropan-1-ol. 14 OH NH OH compound E (i) One of the functional groups in compound E is a phenol. Name the other functional groups in compound E.[1] (ii) Draw the structures of the two organic products formed when compound E is heated under reflux with dilute hydrochloric acid. [2] [Total: 10]OCR 2016<br />
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