Interpretation: The reason for the formation of methyl m -nitrobenzoate instead of ortho and para isomers in the following reaction needs to be explained:
Concept Introduction: The organic reactions where an atom which is attached to an
Answer to Problem 1Q
Due to the presence of an electron-withdrawing group that is ester group (
Explanation of Solution
The methyl benzoate is less reactive towards aromatic electrophilic substitution due to the presence of an electron-withdrawing group that is the ester group,
Due to the -R effect (The withdrawal of electrons from one molecule by the other group in a molecule through delocalization is said to be a negative resonance effect (-R effect)), the
The partial positive charge is present at ortho and para position on the benzene ring and thus, it will deactivate the benzene ring towards electrophilic substitution reactions. The incoming electrophile will attack on a position where the electron density is high that is at the meta position.
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Chapter 43 Solutions
EBK A SMALL SCALE APPROACH TO ORGANIC L
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning