OCR A Jun 2013 Paper 4 Q2

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4-Aminophenol is an organic compound that can behave as an acid and a base. NH2 OH 4-aminophenol (a) State how 4-aminophenol can behave as a base.[1] (b) 4-Aminophenol is produced by the reduction of 4-nitrophenol. Write an equation to show the production of 4-aminophenol from 4-nitrophenol. Use [H] to represent the reducing agent. (c) 4-Nitrophenol can be produced from 4-bromophenol.Complete the mechanism for this reaction.Use +NO2 as the electrophile. Include any intermediate and the products.In the mechanism for this reaction, NO2 substitutes for Br on the ring. Br OHOCR 2013 [1] [4]<br />
 (d) The flowchart below shows some reactions of 4-aminophenol. NH3 +ClOH NH2 Br Br reaction I NH2 OH Na reaction III reaction II 4-aminophenol OH (i) Identity the reagent in reaction I.[1] (ii) Name the organic product of reaction II.[1] (iii) Write the equation for reaction II. (iv) In the box on the flowchart, draw the structure of the organic compound formed by reaction III. [1] [1]OCR 2013 Turn over<br />
 (e) The Sandmeyer reaction can be used to replace a diazonium group, N2 +, with a halogen atom, X, on an aromatic ring. The reagent used for the reaction is a copper(I) halide, CuX. N2 CuX Compound C, shown below, can be synthesised using only 4-aminophenol and other standard laboratory reagents. The flowchart on the next page shows this synthesis. (cid:44) HO OH compound C (i) State a possible use for compound C.[1] (ii) On the flowchart on the next page: state the reagents and conditions used for reaction 1 suggest the structure of compound B suggest the reagent used for reaction 2 state the conditions used for reaction 3. [5]OCR 2013<br />
 NH2 OH 4-aminophenol reaction 1 reagentsconditionsN2 reaction 2 reagentOH compound A compound B reaction 3 conditions(cid:44) HO OH compound COCR 2013 [Total: 16] Turn over<br />

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