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Electrophilic Aromatic Substitution in Organic Chemistry

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Terms in this set (16)

  • What is electrophilic aromatic substitution (EAS)?

    EAS is a reaction where an aromatic ring reacts with an electrophile, replacing a hydrogen atom on the ring.

  • What is sulfonation in aromatic chemistry?

    Sulfonation introduces a sulfonic acid group (-SO3H) onto an aromatic ring using \(\mathrm{SO_3}\\) and \(\mathrm{H_2SO_4}\\).

  • How does the -OCH3 group affect electrophilic aromatic substitution?

    The -OCH3 group is an electron-donating activating group that directs substitution to the ortho and para positions.

  • What is the major product when anisole undergoes sulfonation with SO3/H2SO4?

    The major product is para-methoxybenzenesulfonic acid, with the -SO3H group para to the -OCH3 group due to less steric hindrance.

  • How does the -CO2H group affect bromination of benzoic acid?

    The -CO2H group is electron-withdrawing and deactivates the ring, directing bromination to the meta position.

  • What is the major product of bromination of benzoic acid with Br2/FeBr3?

    The major product is meta-bromobenzoic acid, with bromine at the meta position relative to the -CO2H group.

  • How does the -OCH2Ph substituent affect bromination of aromatic ethers?

    The -OCH2Ph group is an activating, ortho/para-directing substituent, favoring bromination at these positions.

  • What is the major product of bromination of phenyl benzyl ether with Br2/FeBr3?

    The major product is para-bromobenzyl phenyl ether, with bromine at the para position to the -OCH2Ph group.

  • What is Friedel-Crafts alkylation?

    Friedel-Crafts alkylation introduces an alkyl group onto an aromatic ring using an alkyl halide and AlCl3 as a catalyst.

  • How does the -OCH2Ph group influence Friedel-Crafts alkylation?

    The -OCH2Ph group activates the ring and directs alkylation to the ortho and para positions.

  • What is the major product when phenyl benzyl ether reacts with CH3CH2Cl/AlCl3?

    The major product is para-ethylbenzyl phenyl ether, with the ethyl group at the para position to the -OCH2Ph group.

  • What is nitration in aromatic chemistry?

    Nitration introduces a nitro group (-NO2) onto an aromatic ring using \(\mathrm{HNO_3}\\) and \(\mathrm{H_2SO_4}\\).

  • How do ethyl (-CH2CH3) and ethoxy (-OCH2CH3) groups affect nitration?

    Both are activating, ortho/para-directing groups that influence the nitro group to add ortho or para to them.

  • Where does nitration occur on a benzene ring with both ethyl and ethoxy substituents?

    The nitro group adds at a position ortho to the ethyl group and para to the ethoxy group, favored by combined directing effects.

  • How does the -OCH3 group affect nitration on biphenyl systems?

    The -OCH3 group activates the ring and directs nitration to the ortho and para positions, with para favored due to less steric hindrance.

  • What is the major mononitration product of a biphenyl with a methoxy substituent?

    The nitro group is introduced at the para position relative to the -OCH3 group on the biphenyl ring.