Please help me answer the following questions from thepicture:
b) Draw the major products for this reaction
C) Draw the major products
Questions: 3,4,13
NH2 b) #3, Consider the aromatic H resonances of the three possible nitration products. Give a simplified description of what chemical shift and splitting you would expect for each, assuming there is only vicinal coupling at work. #4: Consider the NMR spectrum that follows. Propose a candidate structure that would be consistent with a by product of the reaction we just completed. (Hint: Assume the proton integrations are equal and equal to 3H) #5: Write the chemical reaction showing how the electrophile for the nitration of methyl benzoate was formed. #6: Why does methyl benzoate, which is water insoluble, dissolve in concentrated Hzso4? #7: In the nitration of methyl benzoate, which undesired products may have formed which would have lowered the yield? What procedural error may have led to these products? #8: The nitro substituent was introduced in the meta position of the methyl benzoate. Why does it preferentially occur at meta, other than para or ortho? Show structures to prove your reasoning. (Be aware that it preferentially goes to meta, which means that the other reactions are not totally excluded) #9: Calculate the percent yield and percent recovery for today's reaction. (Hint: To determine if the acids are limiting reagent, you must know the concentration of the acids) #10: Label the IR spectra in the book and the IR and NMR spectra obtained in lab. Does the final spectrum indicate product? Why? Identify any impurities in spectra and suggest methods for removing these impurities. Can you tell if your product is dinitrated from the IR? 11 During the procedure, several washes with cold methanol were done. Why was it important to use cold methanol? #12: Why was it important to use a minimum amount of methanol for recrystallization? #13: What species removes the hydrogen from the spa carbon in the cationic reaction intermediate to allow the aromatic ring to reform?
