Describe a suitable method for investigating the rate of this reaction at $40^\circ\text{C}$, using the following: • a $0.10\,\mathrm{mol\,dm^{-3}}$ solution of 1-chloro-1-phenylethane, labelled A • a $0.10\,\mathrm{mol\,dm^{-3}}$ solution of sodium hydroxide, labelled B • $0.10\,\mathrm{mol\,dm^{-3}}$ HCl • volumetric glassware • ice-cold solvent • stopclock • access to standard laboratory equipment and chemicals
Deduce the order of reaction with respect to each of $[\mathrm{C_6H_5CHClCH_3}]$ and $[\mathrm{OH^-}]$. Explain your answer.
Write the rate equation for this reaction, and state the units of the rate constant, $k$.
Calculate the relative rate for experiment 4.
Use your answers in (b)(i) to help you draw the mechanism for the reaction of 1-chloro-1-phenylethane with hydroxide ions, including: • all relevant lone pairs and dipoles • curly arrows to indicate electron-pair movement • the structures of any transition state or intermediate
A single optical isomer of 1-chloro-1-phenylethane was used in this reaction. 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.
A proton NMR spectrum of 1-phenylethanol contains four peaks: a multiplet for the $\mathrm{C_6H_5}$ protons and three additional peaks as listed in the table. After the sample is shaken with $\mathrm{D_2O}$ and the proton NMR spectrum is taken again, fewer peaks are observed. Complete the table for the proton NMR spectrum of 1-phenylethanol, $\mathrm{C_6H_5CH(OH)CH_3}$. Use the Data Booklet might be helpful.