Aniline (PhNH2) cannot be brominated using Br2/FeBr3. Why not? a. The Lewis acid

Question

Aniline (PhNH2) cannot be brominated using Br2/FeBr3. Why not?

a. The Lewis acid FeBr3 binds to the amine lone pair, deactivating the ring and tying up the Lewis Acid needed to activate Br2.

b. An amine is a highly deactivating directing group.

c. FeBr3 is a strong base and deprotonates the N-H group of the amine.

d. FeBr3 competes with Br+ as an electrophile, and substitutes for H+.

a. The Lewis acid FeBr3 binds to the amine lone pair, deactivating the ring and tying up the Lewis Acid needed to activate Br2.

b. An amine is a highly deactivating directing group.

c. FeBr3 is a strong base and deprotonates the N-H group of the amine.

d. FeBr3 competes with Br+ as an electrophile, and substitutes for H+.

Explanation / Answer

a. The Lewis acid FeBr3 binds to the amine lone pair, deactivating the ring and tying up the Lewis Acid needed to activate Br2.

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