AQA Jun 2014 Paper 4 Q8

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do not write outside the box this question is about some isomers of c h o a compound h is a cyclic ester that can be prepared as shown on the structure of h two of the carbon atoms are labelled hoch ch ch ch cocl a ch c h c h c h c b o hcl a i name and outline a mechanism for this reaction use table c on the data sheet to give the c n m r value for the carbon atom labelled a and the value for the carbon atom labelled b marks wmp jun chem do not write outside the box a ii hoch ch ch ch cocl can also react to form a polyester in a mechanism similar to that in question a i draw the repeating unit of the polyester and name the type of polymerisation involved marks b state how you could distinguish between compounds j and k by a simple test tube reaction state how you could distinguish between j and k by giving the number of peaks in the h n m r spectrum of each compound marks ch c ch c ch ch c ch ch c o h question continues on the next page turn over wmp jun chem do not write outside the box c draw the structure of each of the following isomers of c h o label each structure you draw with the correct letter l m n p or q l is methyl methylpropenoate m is an ester that shows e z stereoisomerism n is a carboxylic acid with a branched carbon chain and does not show stereoisomerism p is an optically active carboxylic acid q is a cyclic compound that contains a ketone group and has only two peaks in its h n m r spectrum marks end of questions wmp jun chem

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