AQA Jun 2012 Paper 4 Q4

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do not write outside the box a acyl chlorides and acid anhydrides are important compounds in organic synthesis outline a mechanism for the reaction of ch ch cocl with ch oh and name the organic product formed mechanism name of organic product marks b a polyester was produced by reacting a diol with a diacyl chloride the repeating unit of the polymer is shown below o c ch ch c o ch ch ch ch ch b i name the diol used mark b ii draw the displayed formula of the diacyl chloride used mark wmp jun chem do not write outside the box b iii a shirt was made from this polyester a student wearing the shirt accidentally splashed aqueous sodium hydroxide on a sleeve holes later appeared in the sleeve where the sodium hydroxide had been name the type of reaction that occurred between the polyester and the aqueous sodium hydroxide explain why the aqueous sodium hydroxide reacted with the polyester type of reaction explanation marks c i complete the following equation for the preparation of aspirin using ethanoic anhydride by writing the structural formula of the missing product cooh oh h c h c cooh aspirin ch mark c ii suggest a name for the mechanism for the reaction in part c i mark c iii give two industrial advantages other than cost of using ethanoic anhydride rather than ethanoyl chloride in the production of aspirin advantage advantage marks question continues on the next page turn over wmp jun chem do not write outside the box d complete the following equation for the reaction of one molecule of benzene dicarboxylic anhydride phthalic anhydride with one molecule of methanol by drawing the structural formula of the single product ch oh e the indicator phenolphthalein is synthesised by reacting phthalic anhydride with phenol as shown in the following equation mark oh conc h so heat oh c oh h o phenol phenolphthalein e i name the functional group ringed in the structure of phenolphthalein mark e ii deduce the number of peaks in the c n m r spectrum of phenolphthalein mark e iii one of the carbon atoms in the structure of phenolphthalein shown above is labelled with an asterisk use table on the data sheet to suggest a range of values for the peak due to this carbon atom in the c n m r spectrum of phenolphthalein mark wmp jun chem do not write outside the box f phenolphthalein can be used as an indicator in some acid alkali titrations the ph range for phenolphthalein is f i for each acid alkali combination in the table below put a tick in the box if phenolphthalein could be used as an indicator acid alkali tick box sulfuric acid sodium hydroxide hydrochloric acid ammonia ethanoic acid potassium hydroxide nitric acid methylamine f ii in a titration nitric acid is added from a burette to a solution of sodium hydroxide containing a few drops of phenolphthalein indicator give the colour change at the end point mark marks turn over for the next question turn over wmp jun chem

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