AQA Jun 2011 Paper 4 Q5

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do not write outside the box items softened with plasticisers have become an essential part of our modern society compound s shown below is commonly known as phthalic acid esters of phthalic acid are called phthalates and are used as plasticisers to soften polymers such as pvc poly chloroethene cooh cooh a give the iupac name for phthalic acid mark b draw the displayed formula of the repeating unit of poly chloroethene mark question continues on the next page turn over wmp jun chem do not write outside the box c the ester diethyl phthalate dep is used in food packaging and in cosmetics c i complete the following equation showing the formation of dep from phthalic anhydride cooch ch cooch ch dep marks c ii deduce the number of peaks in the c n m r spectrum of dep mark c iii one of the peaks in the c n m r spectrum of dep is at ppm table on the data sheet can be used to identify a type of carbon atom responsible for this peak draw a circle around one carbon atom of this type in the structure below cooch ch cooch ch d the mass spectrum of dep includes major peaks at m z the molecular ion and at m z write an equation to show the fragmentation of the molecular ion to form the fragment that causes the peak at m z mark marks wmp jun chem do not write outside the box e because of their many uses phthalates have been tested for possible adverse effects to humans and to the environment the european council for plasticisers and intermediates is an organisation that represents the manufacturers of plasticisers the text below is taken from a document written by the organisation research demonstrates that phthalates at current and foreseeable exposure levels do not pose a risk to human health or to the environment experimental evidence shows that phthalates are readily biodegradable and do not persist for long in the environment e i hydrolysis of dep in an excess of water was found to follow first order kinetics write a rate equation for this hydrolysis reaction using dep to represent the ester mark e ii suggest what needs to be done so that the public could feel confident that the research quoted above is reliable marks extra space turn over wmp jun chem

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