Edexcel Jan 2010 Paper 2 Q18

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PMT 18 Butan-1-ol and three other alcohols, X, Y and Z, are isomers. (a) (i) Give TWO observations you would make when any one of the alcohols reacts with sodium. (2)(ii) Give the molecular formula of the organic product of the reaction. (1)(b) Isomer X does not react with a mixture of potassium dichromate(VI) and sulfuric acid. Draw the displayed formula of X and name it. (2) Name(c) When isomer Y is heated under reflux with a mixture of potassium dichromate(VI) and sulfuric acid, it forms 2-methylpropanoic acid. Deduce the structural formula of the alcohol Y. (1) 14 *N35692A01424*<br /> PMT (d) (i) Isomer Z reacts with a mixture of potassium dichromate(VI) and sulfuric acid to form a compound Q, which does not react with Fehlings or Benedicts solution. Deduce the structural formula of the alcohol Z. (ii) What would be the principal difference between the infrared spectrum of Q and the infrared spectrum of 2-methylpropanoic acid? You are not expected to quote absorption values. (1) (1)(e) One of the isomers, X, Y or Z can be converted to 2-chlorobutane. What reagent would you use to carry out this conversion? (1)(f) (i) 2-chlorobutane reacts with silver nitrate in a mixture of ethanol and water as a solvent. What would you see when the reaction occurred? (1)*(ii) Both ethanol and water contain hydrogen bonds. By considering the hydrogen bonding on these two solvents, suggest why 2-chlorobutane is more soluble in ethanol than in water. (2)(Total for Question 18 = 12 marks) *N35692A01524* 15 Turn over<br />

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