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For the nitration or bromination of anisole, why is the meta product only obtained in minimal amounts?Select answer from the options belowThe intermediate sigma complex formed has the lowest energy and therefore the lowest energy of activation.The intermediate sigma complex formed has the highest energy and therefore the largest energy of activation.The intermediate sigma complex formed has the fewest configurations and therefore is the lowest in energy.The intermediate sigma complex formed has the most configurations and therefore is the highest in energy.

Question

For the nitration or bromination of anisole, why is the meta product only obtained in minimal amounts?Select answer from the options belowThe intermediate sigma complex formed has the lowest energy and therefore the lowest energy of activation.The intermediate sigma complex formed has the highest energy and therefore the largest energy of activation.The intermediate sigma complex formed has the fewest configurations and therefore is the lowest in energy.The intermediate sigma complex formed has the most configurations and therefore is the highest in energy.

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Solution

The intermediate sigma complex formed has the lowest energy and therefore the lowest energy of activation.

This is because anisole is an aromatic ether and the methoxy group (-OCH3) attached to the benzene ring is an activating group. This group directs the electrophilic substitution to the ortho and para positions of the benzene ring due to the +M (mesomeric) effect, which increases the electron density at the ortho and para positions.

The intermediate sigma complexes formed at the ortho and para positions are lower in energy compared to the meta position, making the formation of the ortho and para products more favorable. Therefore, the meta product is only obtained in minimal amounts.

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