Edexcel Jan 2012 Paper 6 Q1

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Answer ALL the questions. Write your answers in the spaces provided. PMT 1 Three compounds A, B and C are subjected to a series of chemical tests. Some information about these compounds is given below. (cid:120)(cid:3) The three compounds are isomers with molecular formula C3H6O.A and B contain only one functional group, but C contains two separate functional (cid:3) (cid:3) (cid:3) groups. (cid:120)(cid:3) None of the three compounds contains a ring of atoms. In each of the three compounds the oxygen atom is bonded to only one carbon atom. (cid:120)(cid:3) (a) (i) A and B are tested separately with 2,4-dinitrophenylhydrazine solution and both give an orange precipitate. When A and B are heated separately with a mixture of potassium dichromate(VI) and dilute sulfuric acid, the solution containing B turns from orange to green. The solution containing A remains orange. Use these results and the information at the start of the question to deduce displayed formulae for A and B. (2) *P35988A0216*<br /> (ii) PMT PPM State whether this is the nmr spectrum of A or B. Justify your answer. Explain how the nmr spectrum of the other isomer will differ. (2)*P35988A0316* Turn over<br /> (b) (i) C does not react with 2,4-dinitrophenylhydrazine. When C is heated with acidified potassium dichromate(VI), the solution turns from orange to green. When C is shaken with bromine water, the bromine water quickly turns colourless. Name the two functional groups present in C. PMT (2)(ii) State two observations you would expect to make when a small piece of sodium is added to C. (2)(iii) Draw two possible displayed formulae for C which are consistent with the above information. (2) (Total for Question 1 = 10 marks) *P35988A0416*<br />

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