Edexcel Jun 2012 Paper 6 Q2

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2 This question is about some reactions of phenol and cyclohexanol. OH OH phenol cyclohexanol (a) Give two observations you would make when bromine water is added, drop by drop, to an aqueous solution of phenol. (2)(b) (i) What is observed when cyclohexanol is warmed with a mixture of aqueous potassium dichromate(VI) and sulfuric acid? (1)(ii) Give the skeletal formula of the organic product of the reaction in (b)(i). (iii) What change, if any, is observed when the organic product of the reaction in (b)(i) is mixed with the following reagents? 2,4-dinitrophenylhydrazine solution (1) (2)Tollens reagent(c) Both phenol and cyclohexanol react with ethanoyl chloride to produce steamy fumes and an ester. Phenol behaves like an alcohol in this reaction. (i) How could you show that the steamy fumes were due to the presence of a hydrogen halide, which in this case is hydrogen chloride? (2)*P39311A0416*<br /> (ii) The infrared spectrum below is for the ester produced in the reaction of ethanoyl chloride with phenol. 100 Transmittance / % 50 0 4000 Bond C H O H C O C C C O 3000 2000 1500 1000 500 Wavenumber / cm1 Group alkanes arenes alcohols and phenols Wavenumber range / cm1 29622853 3030 37503200 ethanoates benzoates arenes ketones esters 12501190 13101250 and 11501100 1600, 1580, 1500, 1450 17001680 17701715 Identify the bond and group which cause each of the absorptions X and Y. (2) XY*P39311A0516* Turn over<br /> (iii) Draw the structural formula of the ester produced in the reaction of ethanoyl chloride with phenol. (1) (Total for Question 2 = 11 marks) *P39311A0616*<br />

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