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2.

Draw all resonance structures for each compound
and use the resonance structures to determine if the
substituent has an electron-donating or electronwithdrawing resonance effect

a. electron- donating

b. electron-withdrawing .

Rank the compound in each group in order of increasing reactivity in electrophilic aromatic substitution (2 ) (1) (2 ) (1) (3 ) (3 ) .7.

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10. Draw the product formed when each compound is treated with HNO₃ and H₂SO₄ .

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a synthetic intermediate used in the synthesis of the anti-inflammatory agent ibuprofen . What steps are needed to convert benzene into p-isobutylacetophenone.15.

Starting with aniline. outline a synthesis of each of the following: a.18. p-bromoaniline .

b. o-bromoaniline .

c. 2-bromo-4-nitroaniline .

4-bromo-2-nitroaniline .d.