Organic Chemistry - Effect of methyl substituent in Aromatic Substitution via Benzyne
The Me group has no directing effect in the deprotonation so there are 2 protons (o &amp; p) that can be removed with equal probability by the NaNH2 to give the benzyne. These give 2 possible benzynes (2 and 3 relative to Me). The nucleophile will add with equal facility to either end of either benzyne giving a mixture of 3 isomers in 1:2:1 ratio. The major isomer is the m- aminotoluene because it can arise from both of the possible benzynes.