As a side-product, this reaction also produces an isomer of 4-nitromethylbenzene. Draw the structure of that side-product.
Write an equation for the reaction of $\text{HNO}_3$ with $\text{H}_2\text{SO}_4$ that generates the electrophile for this reaction.
Describe the ways in which the structure and bonding of the six-membered ring in intermediate T are different from those in methylbenzene.
Give the systematic name for compound W.
Suggest the reagents and conditions needed for steps 1-5.
Suggest how the basicity of benzocaine compares with that of ethylamine. Explain your answer.
Predict how many peaks would appear in the carbon-13 NMR spectrum.
Benzocaine was dissolved in $\text{CDCl}_3$, and the proton NMR spectrum of the solution was recorded. Suggest why $\text{CDCl}_3$ is chosen instead of $\text{CHCl}_3$ as the solvent for recording a proton NMR spectrum.
Use the Data Booklet together with 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 are shown.
Explain why the absorption at $\delta 1.2\,\text{ppm}$ has that splitting pattern.
The proton NMR spectrum of benzocaine dissolved in $\mathrm{D_2O}$ was recorded. Suggest how this spectrum would be different from the spectrum in (d)(ii). Explain your answer.
Suggest the reagents for step 1.
Suggest the structures of compounds R and S and draw them in the boxes.