Question

Hydrogens on these molecular features can be targeted by nitroalkanes via the vicarious release of a besyl (“beh-sill”) group. Arrows drawn across these features indicate valid sites for “migration” using a rule developed by Erich Clar. Alkyl groups on these features can be rearranged by heating over a zeolite to adjust the ratio of BTX compounds. Amines on these features are replaced by in situ transformation into a salt with nitrous (10[1])acid, followed by cleavage in the presence of copper. Nucleophiles perform a frontside attack at the ipso position (10[1])of these structures, (10[2]-5[1])forming an intermediate (10[1])whose charge is delocalized over five carbons. (10[1])Adding a directing (10[1])group (10[1])to these structures (10[1])can constrain later substitutions to the o- and (10[1])p- (10[1])positions. (10[2])For (10[1])10 points, what structures (10[1])are targeted for electrophilic substitution in a Friedel–Crafts (10[1]-5[1])reaction? ■END■ (10[3])

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