Edexcel Jan 2017 (IAL) Paper 4 Q22

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22 This question is about the isomers P and Q. P Q CH3COCH(CH3)2 CH3CH2COCH2CH3 (a) Identify the reagent used in a test to show that P and Q are both carbonyl compounds. Give the positive result of the test. (2) ReagentResult(b) Identify the reagents used in a test which gives a positive result with P but not with Q. Give the positive result of the test and identify the organic product which is observed. (3) ReagentsResultIdentity of organic product(c) Name the organic product formed when P reacts under suitable conditions with lithium tetrahydridoaluminate(III). (1)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 *P48372RA01528* 15 Turn over<br /> (d) The proton nmr spectra of P and Q were compared. Complete the table. (4) CH3COCH(CH3)2 CH3CH2COCH2CH3 Number of peaks in the low resolution nmr spectrum Number of H atoms producing peak with the greatest area in low resolution nmr spectrum Splitting pattern of the peak with greatest area in the high resolution nmr spectrum (e) A sequence of reactions was carried out with Q. CH3CH2COCH2CH3 HCN in the presence of NaCN Compound R reagent A OH CH3CH2CCH2CH3 COOH Compound S heat with an acid catalyst Polymer T 16 *P48372RA01628* 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 /> (i) Complete the mechanism for the reaction of Q with HCN in the presence of NaCN, showing relevant curly arrows, lone pairs, charges and dipoles. CH3CH2CCH2CH3 C N (ii) Identify the reagent A used to convert compound R to compound S. (4) (1)(iii) Draw the displayed formula of two repeat units of polymer T. (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 *P48372RA01728* 17 Turn over (Total for Question 22 = 17 marks)<br />

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