When o-fluorotoluene is treated with sodium amide, the product is ________.

A) only o-toluidine
B) only m-toluidine
C) only p-toluidine
D) a mixture of o- and p-toluidine
E) a mixture of o- and m-toluidine.

The reaction of o-fluorotoluene with sodium amide causes an elimination reaction to form a mixture of m-toluidine and o-toluidine. The amide ion removes the acidic proton of the methyl group, and the fluoride leaves as a leaving group which forms a negatively charged intermediate. The intermediate then reforms to form two different regioisomers, o-toluidine and m-toluidine. Therefore, the best choice is E, a mixture of o- and m-toluidine.