This reaction also yields an isomer of 4-nitromethylbenzene as a side-product. Draw the structure of this side-product.
Write an equation for the reaction between $\text{HNO}_3$ and $\text{H}_2\text{SO}_4$ that produces the electrophile for this reaction.
Describe how the structure and bonding of the six-membered ring in intermediate T differs from that in methylbenzene.
Give the systematic name of compound W.
Suggest the reagents and conditions for steps 1-5.
Suggest how the basicity of benzocaine would compare to that of ethylamine. Explain your answer.
Predict the number of peaks that would be observed in the carbon-13 NMR spectrum.
Suggest why $ CDCl$_3$ and not $ CHCl$_3$ is used as the solvent when obtaining a proton NMR spectrum.
Use the Data Booklet and the spectrum in (d)(ii) to complete the table for the proton NMR spectrum of benzocaine. The actual chemical shifts, $\delta$, for the four absorptions have been added.
Explain the splitting pattern for the absorption at $\delta = 1.2\,\text{ppm}$.
The proton NMR spectrum of benzocaine dissolved in D$_2$O was recorded. Suggest how this spectrum would differ from the spectrum in (d)(ii). Explain your answer.
Suggest the reagents used for step 1.
Suggest structures for compounds R and S and draw them in the boxes.