Here in Chapter 23, we learned that aniline becomes highly deactivated in the presence of a strong Lewis acid, due to coordination of the N atom to the Lewis acid. Thus, as shown below at the left, Friedel-Crafts reactions involving aniline are unfeasible. As shown in the reaction below at the right, though, this does not appear to be a problem with the N atom in pyrrole. Explain why. NH2 `CI CI No reaction Lewis acid Lewis acid catalyst catalyst

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Here in Chapter 23, we learned that aniline becomes highly deactivated in the presence of a strong Lewis acid, due to
coordination of the N atom to the Lewis acid. Thus, as shown below at the left, Friedel-Crafts reactions involving aniline
are unfeasible. As shown in the reaction below at the right, though, this does not appear to be a problem with the N
atom in pyrrole. Explain why.
NH2
`CI
CI
No reaction
Lewis acid
Lewis acid
catalyst
catalyst
Transcribed Image Text:Here in Chapter 23, we learned that aniline becomes highly deactivated in the presence of a strong Lewis acid, due to coordination of the N atom to the Lewis acid. Thus, as shown below at the left, Friedel-Crafts reactions involving aniline are unfeasible. As shown in the reaction below at the right, though, this does not appear to be a problem with the N atom in pyrrole. Explain why. NH2 `CI CI No reaction Lewis acid Lewis acid catalyst catalyst
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