OCR A Jun 2014 Paper 4 Q2

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The following three carbonyl compounds are structural isomers of C5H10O2. OH HO O compound C OH compound D compound E (a) Describe chemical tests that you could carry out in test-tubes to distinguish between compounds C, D and E. Include appropriate reagents and any relevant observations. Also include equations showing structures for the organic compounds involved.[4]OCR 2014<br />
 (b) Aldehydes and ketones are both reduced by NaBH4. When used in the presence of a CeCl 3 catalyst, NaBH4 only reduces ketones. Compound F has the structural formula CH3COCH2CH2CHO. It is reduced by NaBH4 in the presence of a CeCl 3 catalyst to form one of the compounds C, D or E. Show the mechanism for this reduction of compound F and identify the product that is formed. Use curly arrows and show relevant dipoles. You do not need to show the role of the CeCl 3 catalyst. (c) Predict the number of peaks in the 13C NMR spectra of compounds C, D and E. Compound Number of peaks [4] [1]OCR 2014 Turn over<br />
 (d) Ozonolysis is a technique used in organic chemistry to break open a C=C double bond. 10 During ozonolysis, an alkene reacts with ozone, O3. The products are carbonyl compounds, as shown below. R' O3 R' (i) Draw the structures of the products you would expect from the complete ozonolysis of the following alkenes.pent-2-enehexa-2,4-diene (ii) In another ozonolysis reaction, organic compound G reacted hexane-1,6-dial. to form only [3] Compound G has six carbon atoms. Draw the structure of compound G.OCR 2014 [1] [Total: 13]<br />
 11 BLANK PAGE Question 3 begins on page 12 PLEASE DO NOT WRITE ON THIS PAGEOCR 2014 Turn over<br />

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