Edexcel Jun 2017 Paper 4 Q17

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(3) (2) 17 Ethanol reacts with a carboxylic acid, P, to produce an ester, Q. (a) Carboxylic acid P contains 58.8 % carbon and 9.8 % hydrogen by mass. The mass spectrum of compound P has the molecular ion peak at m / e = 102. Use all these data to confirm that the molecular formula of P is C5H10O2 . (b) Draw the displayed formulae of the four possible structures of carboxylic acid P. Carboxylic acid 1 Carboxylic acid 2 Carboxylic acid 3 Carboxylic acid 4 20 *P48082A02028* D O N O T W R I T E I N T H I S A R E A D O N O T W R I T E I N T H I S A R E A D O N O T W R I T E I N T H I S A R E A<br /> (c) The mass spectrum of carboxylic acid P has a major peak at m / e = 43. Draw the structures of two species that could give this peak. (d) Use your answers to (b) and (c) to identify which two of the carboxylic acids you have drawn in (b) could be carboxylic acid P. (e) Draw the displayed formulae of the two possible ethyl esters that could be Q. (2) (1) (2) A E R A S I H T N I E T I R W T O N O D A E R A S I H T N I E T I R W T O N O D A E R A S I H T N I E T I R W T O N O D *P48082A02128* 21 Turn over<br /> (f) Information from the high resolution proton nmr spectrum of ester Q is given. Peak Chemical shift,/ ppm for TMS Splitting pattern Relative area below peak 0.96 1.26 2.10 2.20 4.13 doublet triplet split into 9 doublet quartet Use the data from the table to determine the displayed formula of ester Q. Draw the formula below and on it label the protons responsible for the peaks A to E. Explain the splitting pattern in peak B. (5) Displayed formula of Q Explanation of splitting pattern in peak B(Total for Question 17 = 15 marks) TOTAL FOR SECTION B = 48 MARKS 22 *P48082A02228* D O N O T W R I T E I N T H I S A R E A D O N O T W R I T E I N T H I S A R E A D O N O T W R I T E I N T H I S A R E A<br />

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