Denisse Cuarteros

Chem 243B-001
Laboratory 3B: Nitration of Methyl Benzoate, a Macroscale Synthesis
Dont forget to turn in your NMR with complete analysis. (Short response)

1. Define electrophile and explain what makes nitronium an electrophile.
Electrophile is an electron-loving molecule that participates in a chemical reaction by
accepting a pair of electrons from a nucleophile (electron-rich). Most electrons are
positively-charged Lewis acids like nitronium. Nitronium is an electrophile because it is
positively-charged (cation) and is electron poor. It is also reactive because it wants a pair of
electrons to be bonded to it, to become stable.
2. Why did we use methyl benzoate instead of benzene or phenol?
Methyl benzoate was used because it is deactivating group and is a meta-director. If either
benzene or phenol was used, the main product will not be a meta-product but it will have
ortho/para products.
3. What technique was used during work-up? Explain how this purified the product.

The technique used was called recrystallization. Recrystallization is a very common
technique to purify crude crystals to increase the purity of the product because it reduces
contamination by increasing its crystal lattice. Washing the crystals with methanol will
remove contaminants because methyl-m-nitrobenzoate is insoluble in the presence of
methanol; thus, increasing its purity.
4. Why is it necessary to maintain the reaction temp below 15 C?
It is very necessary to keep the reaction mixture below 15 C because if the addition is too
fast and the temperature is too high, the yield of the desired product will be lower because the
side products will form faster. Another reason is because the reaction is kinetically favored
since the temperature is kept low (to increase yield) and sulfuric acid was used as a catalyst
to speed up the reaction.