AQA Jun 2015 Paper 4 Q10

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the following five isomers p q r s and t were investigated using test tube reactions and also using n m r spectroscopy do not write outside the box ch ch c c ch ch ch ch c c ch ch h c oh h c c c ch ch ch oh ch a a simple test tube reaction can be used to distinguish between isomers p and s identify a reagent or combination of reagents you could use state what you would observe when both isomers are tested separately with this reagent or combination of reagents marks wmp jun chem b a simple test tube reaction can be used to distinguish between isomer q and all the other isomers do not write outside the box identify a reagent or combination of reagents you could use state what you would observe when q is tested with this reagent or combination of reagents marks c state which one of the isomers p q r s and t has the least number of peaks in its h n m r spectrum give the number of peaks for this isomer marks d write the molecular formula of the standard used in c n m r spectroscopy give two reasons why this compound is used marks question continues on the next page turn over wmp jun chem do not write outside the box e figure and figure show the c n m r spectra of two of the five isomers figure figure ppm ppm the structures of the five isomers are repeated to help you answer this question ch ch c c ch ch ch ch c c ch ch h c oh h c c c ch ch ch oh ch wmp jun chem do not write outside the box state which isomer produces the spectrum in figure and which isomer produces the spectrum in figure explain your answer you do not need to identify every peak in each spectrum use table c on the data sheet to answer the question marks f u and v are other isomers of p q r s and t the h n m r spectrum of u consists of two singlets v is a cyclic alcohol that exists as optical isomers draw the structure of u and the structure of v marks turn over wmp jun chem

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