AQA Jun 2016 Paper 4 Q4

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do not write outside the box compound x clch cocl is used as a reagent in organic synthesis a the mass spectrum of x contains several molecular ion peaks a i chlorine exists as the isotopes cl and cl in a ratio calculate the m z value of the most abundant molecular ion peak in the mass spectrum of x mark a ii the most abundant fragment ion in the mass spectrum of x has m z draw the displayed formula of this fragment ion mark a iii a molecular ion of x that contains one cl atom and one cl atom undergoes fragmentation to form an ion with m z and one other species write an equation for this fragmentation show which isotope of chlorine is present in each product species marks b one important reaction of x is in the preparation of compound p as shown alcl cl ch c cl ch cl hcl wmp jun chem b i draw the structure of the electrophile formed by the reaction of x with alcl do not write outside the box mark b ii outline the mechanism for the reaction of the electrophile from part b i with benzene in the preparation of p marks c compound q is an alternative product that could be formed when x reacts with benzene cl ch describe how you could distinguish between p and q by a test tube reaction give the reagent used and the observation with each compound marks reagent observation with p observation with q turn over wmp jun chem do not write outside the box d x is also used to make the compound hoch cooh this compound is polymerised to form the polymer known as pga pga is used in surgical sutures stitches d i draw the repeating unit of pga mark d ii production of pga occurs via a cyclic compound two hoch cooh molecules react together to form the cyclic compound and two molecules of water draw the structure of this cyclic compound mark e poly propene is also used in surgical sutures e i draw the repeating unit of poly propene mark wmp jun chem do not write outside the box e ii suggest an advantage of surgical sutures made from pga rather than from poly propene explain your answer marks turn over for the next question turn over wmp jun chem

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