Edexcel Jan 2016 (IAL) Paper 2 Q21

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SECTION B Answer ALL the questions. Write your answers in the spaces provided. 21 Cyclopentene is a cyclic alkene and cyclopentanol is a cyclic alcohol. (a) Some reactions involving cyclopentene and cyclopentanol are shown in the flowchart. Complete the displayed formulae in the boxes to show the compounds A, B and C, which are the organic products of the reactions. (3) H H cyclopentanol K2Cr2O7(aq) with H2SO4(aq) heat under reflux H H cyclopentene H2(g) with Ni(s) catalyst Br2(l) compound A compound B compound C 10 *P46938A01024* 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 />
 (b) Give the colour change that would be observed in the reaction between liquid bromine, Br2, and excess cyclopentene. Fromto(c) Bromocyclopentane reacts when heated with aqueous sodium hydroxide solution, according to the following equation. CH2 CH2 H2C CH2 + NaOH H2C CH2 + NaBr H2C CHBr H2C CHOH (i) Complete the mechanism for this reaction on the following diagram. Use curly arrows where necessary and show any relevant dipoles. (1) (3) CH2 CH2 H2C CH2 H2C CH2 +H2C Br H2C CHOH HO (ii) Classify both the type of reaction and mechanism shown in (c)(i). (2) Type of reaction:Mechanism:(iii) What type of bond fission occurs in this reaction? (1)(Total for Question 21 = 10 marks) 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 *P46938A01124* 11 Turn over<br />

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