The reaction between 1-chloro-1-phenylethane and hydroxide ions to produce 1-phenylethanol is: C₆H₅CH(Cl)CH₃ + OH⁻ → C₆H₅CH(OH)CH₃ + Cl⁻ 1-chloro-1-phenylethane 1-phenylethanol The rate of this reaction can be studied by measuring the amount of hydroxide ions that remain in solution at a given time. The reaction can effectively be stopped if the solution is diluted with an ice-cold solvent.

1. (a)Describe a suitable method for studying the rate of this reaction at a temperature of 40°C, given the following. • a solution of 0.10 mol dm⁻³ 1-chloro-1-phenylethane, labelled A • a solution of 0.10 mol dm⁻³ sodium hydroxide, labelled B • 0.10 mol dm⁻³ HCl • volumetric glassware • ice-cold solvent • stopclock • access to standard laboratory equipment and chemicals[4]
2. (b)(i)The rate of this reaction was measured at different initial concentrations of the two reagents. The table shows the results obtained. ``` experiment [C₆H₅CH(Cl)CH₃] /mol dm⁻³ [OH⁻] /mol dm⁻³ relative rate 1 0.05 0.10 0.5 2 0.10 0.20 1.0 3 0.15 0.10 1.5 4 0.20 0.15 to be calculated ``` Deduce the order of reaction with respect to each of [C₆H₅CH(Cl)CH₃] and [OH⁻]. Explain your reasoning. order with respect to [C₆H₅CH(Cl)CH₃] ______________ order with respect to [OH⁻] ______________[2]
3. (b)(ii)Write the rate equation for this reaction, stating the units of the rate constant, k. rate = ______________ mol dm⁻³ s⁻¹ units of k = ______________[1]
4. (b)(iii)Calculate the relative rate for experiment 4. relative rate for experiment 4 = ______________[1]
5. (c)(i)Use your answers in (b)(i) to help you to draw the mechanism for the reaction of 1-chloro-1-phenylethane with hydroxide ions, including the following. • all relevant lone pairs and dipoles • curly arrows to show the movement of electron pairs • the structures of any transition state or intermediate[3]
6. (c)(ii)This reaction was carried out using a single optical isomer of 1-chloro-1-phenylethane. Use your mechanism in (i) to predict whether the product will be a single optical isomer or a mixture of two optical isomers. Explain your answer.[1]
7. (d)The proton NMR spectrum of a sample of 1-phenylethanol shows four peaks: a multiplet for the C₆H₅ protons and three other peaks as shown in the table. When the sample is shaken with D₂O and the proton NMR spectrum recorded, fewer peaks are seen. Complete the table for the proton NMR spectrum of 1-phenylethanol, C₆H₅CH(OH)CH₃. Use of the Data Booklet might be helpful. [Figure X.X][4]

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