Question

ОСН, ОСН, OCHZ ОСН, NO2 HNO3 H2SO4 + + NO2 anisole 0-nitroanisole (31%) m-nitroanisole (2%) NO2 p-nitroanisole (67%)

1 - Discuss correctly why each substituent favors the observed major product. (e.g. stability of the carbocation intermediate resonance hybrid, steric hindrance at reaction location) How does the stability of the intermediates (from the handout done during the lab) rationalize the observed products formed? Do more stable intermediate lead to more products or less

2- Create a general rule that correctly correlates EDG/EWG behavior of a substituent and the preferred regiochemistry of the reaction. Where do EDGs tend to substitute? Where do EWGs tend to substitute?

3- Based on relative amount of starting reagent remaining and/or amount of dinitration product produced, correctly rank each substituent in order of most activating to least (i.e. most deactivating) Highlight (do no need to include all but may) the data or make a specific reference to the table/figure where the data is included. Provide the ranking of each starting material from most activated to least activated. Provide an explanation based on the nucleophilicity of the ring to rationalize these rankings. What increases the nucelophilicity of the ring?

4- Correctly relate the order of the activating/deactivating rank of substituents to the EDG/EWG behavior of that group. Between groups that show the same behavior (EDGs compared to other EDGs, and likewise for EWGs) discuss why there may be differences in the reactivity (i.e. do all EDGs have the same amount of reagent left, why or why not?)Which group (EDG or EWG) was activating or deactivating? Do all EDGs or EWGs react the same? Are there differences in how the EDGs and EWGs donate or withdraw electrons? Are there chemical/structural reasons for differences?