Would you expect ortho-dimethoxybenzene or para-dimethoxybenzene to be
nitrated more readily? Justify your choice briefly.
See hint below.
Where is the hint??
To determine which compound, ortho-dimethoxybenzene or para-dimethoxybenzene, would be nitrated more readily, we need to consider the directing influence of the methoxy (-OCH3) groups on the benzene ring.
The methoxy groups are electron-donating groups, which means they increase the electron density of the benzene ring. This electron-donating nature of the methoxy groups activates the benzene ring towards electrophilic aromatic substitution reactions, such as nitration.
However, the position of the methoxy group relative to the nitration site is crucial in determining the reactivity.
In ortho-dimethoxybenzene, the methoxy groups are located in the ortho positions (positions 1 and 2), which are directly adjacent to the potential nitration site. The electron-donating effect of the methoxy groups would increase the electron density at the ortho positions, making them more reactive towards electrophilic attack. Therefore, ortho-dimethoxybenzene would be expected to be nitrated more readily.
On the other hand, in para-dimethoxybenzene, the methoxy groups are located in the para positions (positions 1 and 4), which are diagonally opposite to the potential nitration site. The electron-donating effect of the methoxy groups is less effective at activating the para positions compared to the ortho positions. Hence, para-dimethoxybenzene would be expected to be nitrated less readily than ortho-dimethoxybenzene.
To summarize, ortho-dimethoxybenzene would be expected to be nitrated more readily due to the stronger electron-donating effect of the ortho-positioned methoxy groups, compared to the para-dimethoxybenzene.