CIE Mar 2017 v2 Paper 4 Q9

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This question is about compound T, CxHyOz. 22 PMT (a) Part of the mass spectrum of T is shown. The peak heights of the M and M+1 peaks are 33.9 and 3.4 respectively. 100 80 60 40 20 relative intensity 50 75 125 150 100 m / e (i) Calculate x, the number of carbon atoms present in T. (ii) Deduce the molecular formula of T.[1] x =[2] (iii) The mass spectrum has a peak at m / e = 119. Identify the fragment lost from T to produce this peak.[1]UCLES 2017 9701/42/F/M/17<br /> PMT (b) The infra-red spectrum of T is shown. 23 100 transmittance 50 0 4000 3000 2000 1500 wavenumber / cm1 1000 500 Identify the type of bond responsible for each of the peaks V and W. Use the Data Booklet to help you. VW[1] (c) The proton NMR spectrum of T in CDCl 3 is shown. 3H 3H 4H 11 10 5/ ppm (i) Complete the table for the proton NMR spectrum of T. Use the Data Booklet to help you. type of proton/ ppm 3.9 7.27.9UCLES 2017 9701/42/F/M/17 [1] [Turn over<br /> PMT 24 (ii) The peak at= 2.4 ppm is due to a proton attached to a saturated carbon atom. State the two possible types of proton. 1.2.[1] (iii) Adding D2O to T does not change its proton NMR spectrum. What does this tell you about the functional groups present in T?[1] (d) Use the information to draw two possible structures of T which are functional group isomers of each other. [2] [Total: 10] Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the publisher will be pleased to make amends at the earliest possible opportunity. To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at www.cie.org.uk after the live examination series. Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge.UCLES 2017 9701/42/F/M/17<br />

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