Which is the best prediction of the site(s)of substitution when 3-methylphenol is nitrated?
A)C-2
B)C-4
C)C-5
D)C-6
E)C-4 and C-6

Question

Quizplus · Accepted Answer

The methyl group on the phenol ring is an electron-donating group (EDG) which increases the electron density on the ring, making it easier for the nitration reaction to occur. This EDG effect is strongest at the ortho and para positions (C-2, C-4, C-5, and C-6), making them the most likely sites of substitution. However, the ortho position (C-2) is hindered by the bulky methyl group, making it less accessible to the nitration reagent. Therefore, the para positions (C-4 and C-6) are the most likely sites of substitution, resulting in a mixture of mono- and di-nitro products. Therefore, the best choice is E, C-4 and C-6.

Which Is the Best Prediction of the Site(s)of Substitution When