Reactions of Arenes
For each of the reactions on the left, predict the major organic product. Pay particular attention to the regiochemistry of the reaction (i.e., ortho- para- or meta-directing substituents).Click the mouse on the reactant molecule to view the answer;
click on the reagent to review the mechanism and regiochemistry of the reaction.
Neutral MnO4- will oxidize an aryl side-chain containing at least one benzylic hydrogen to give the aryl carboxylic acid.
Neutral MnO4- will oxidize an aryl side-chain containing at least one benzylic hydrogen to give the aryl carboxylic acid.
Bromine in the presence of FeBr3 will result in the electrophilic addition of Br+ to the aromatic ring. The methoxy group is strongly deactivating and directs substitution ortho- to itself, overwhelming the tendency of the weakly activating methyl group to direct ortho- to itself (and meta- to the methoxy group).
HNO3 in the presence of H2SO4 will result in the electrophilic addition of NO2+ to the aromatic ring. The methyl group is mildly activating and directs substitution ortho- and para- to itself. Excess reagent results in exhaustive nitration.
Neutral MnO4- will oxidize an aryl side-chain containing at least one benzylic hydrogen to give the aryl carboxylic acid.
Neutral MnO4- will oxidize an aryl side-chain containing at least one benzylic hydrogen to give the aryl carboxylic acid.
Bromine in the presence of FeBr3 will result in the electrophilic addition of Br+ to the aromatic ring. The methoxy group is strongly deactivating and directs substitution ortho- to itself, overwhelming the tendency of the weakly activating methyl group to direct ortho- to itself (and meta- to the methoxy group).
HNO3 in the presence of H2SO4 will result in the electrophilic addition of NO2+ to the aromatic ring. The methyl group is mildly activating and directs substitution ortho- and para- to itself. Excess reagent results in exhaustive nitration.