Concept explainers
a)
Interpretation:
The electrostatic potential map of imidazole is given. The most acidic hydrogen atom and most basic hydrogen atom in it are to be identified.
Concept introduction:
Electrostatic potential maps are useful because they show at a glance the electron rich and electron poor atoms in the molecule. The electron rich regions are shown in red and the electron poor regions are shown in blue.
To identify:
The most acidic hydrogen atom and most basic nitrogen atom in imidazole by looking at its electrostatic potential map.
b)
Interpretation:
Structures for the resonance forms of the products that result when imidazole is protonated by an acid and deprotonated by a base are to be drawn.
Concept introduction:
Resonance forms differ only in the placement of their π and nonbonding valence electrons. Neither the position nor the hybridization of any atom changes from one resonance form to another. For writing different resonance forms in the structure given, first a three atom groupings with a multiple bond and a p orbital with pair of electrons is to be identified. Then the exchange of position of double bond and electrons in p orbital will give another resonance form. The shift is represented by a curved arrow.
To identify:
Draw structures for the resonance forms of the products that result when imidazole is protonated by an acid and deprotonated by a base.

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Chapter 2 Solutions
ORGANIC CHEMISTRY W/OWL
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