What is the major product of the nitration reaction of 2-methylacetanilide? Why is it the major product?
To determine the major product of the nitration reaction of 2-methylacetanilide, we need to consider the structure of the starting compound and the reactivity of its different functional groups.
2-methylacetanilide has two main functional groups: an amide (-CONH-) and an aromatic ring. Nitration involves the substitution of a nitro group (-NO2) for a hydrogen atom on an aromatic ring. In this case, the nitration reaction will occur at the para position of the aromatic ring since the methyl group (-CH3) on the ring is electron-donating and activates the para position, making it more reactive than ortho or meta positions.
The major product of the nitration reaction of 2-methylacetanilide is para-nitro-2-methylacetanilide. This is because the para position is the most favorable site for electrophilic aromatic substitution due to the electron-donating effect of the methyl group. The methyl group increases the electron density on the ring, making the para position more nucleophilic and attracting the electrophilic nitronium ion (NO2+). As a result, the nitration reaction predominantly occurs at the para position, leading to the formation of para-nitro-2-methylacetanilide as the major product.
It is important to note that while the para product is the major product, other minor products may also form due to the possibility of substitution occurring at the ortho or meta positions. However, the reactivity of the para position and the electron-donating effect of the methyl group make para-nitro-2-methylacetanilide the primary product.