Dolbier HW Solutions 265

Dolbier HW Solutions 265 - 259 ARENES AND AROMATICITY 11.21...

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11.21 Write structural formulas for the species formed when a proton is transferred to either of the two nitrogens of imidazole. Protonation of N-1: The species formed on protonation of N-1 is not aromatic. The electron pair of N-1 that contributes to the aromatic 6 p -electron system of imidazole is no longer available for this purpose because it is used to form a covalent bond to the proton in the conjugate acid. Protonation of N-3: The species formed on protonation of N-3 is aromatic. Electron delocalization represented by the resonance forms shown allows the 6 p -electron aromatic system of imidazole to be retained in its conjugate acid. The positive charge is shared equally by both nitrogens. 11.22
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This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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