Question

Give a possible explanation for the relative amounts of the isometric methyl nitrobenzoates formed in the nitration reaction. Consider mechanistic effects of the substituents.

Answer 1

Answer:

The electrophilic aromatic substitution reaction nitration is used to nitrate methyl benzoate and acetanilide with a nitronium ion. Crystallization was used to purify the product. The melting point was used to determine its purity and the regiochemistry of the products.

Explanation:

Methyl m-Nitrobenzoate is formed in this

reaction rather that ortho/para isomers

because of the ester group of your starting

product of methylbenzoate. The functional

group of ester is a electron withdrawing group

causing nitrobenzene (N02) to become in the

meta position. Thus N02 is a deactivating

group causing itself to be a meta director.

Basically you must look at the substituents

that are attached to your starting benzene ring

in order to figure out whether your reaction

with be ortho/para directors or meta

directors. If the substituents are electron

withdrawing groups then you will be left with

meta as your product but if your substituents

are electron donating groups then your

product will be ortho/para.