(a) Draw the orbital representation of imidazole. Briefly explain why imidazole is aromatic with particular reference to the nitrogen atom(s).

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter15: Benzene And Aromaticity
Section15.SE: Something Extra
Problem 44AP: N-Phenylsydnone, so-named because it was first studied at the University of Sydney, Australia,...
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QUESTION 3
(a)
Draw the orbital representation of imidazole. Briefly explain
why imidazole is aromatic with particular reference to the
nitrogen atom (s).
(b)
(c)
9
HN-
10
7
i) PhLi
ii) (CH3)2CO
iii) H3O*
NH
5.2
Protonated triethylamine, pyridine, imidazole and pyrrole
have pka values 9, 7, 5.2, -4.0, respectively. Give a clear
explanation for the observed values.
H,CO, Me,NH, HOẶC
Draw chemical mechanisms for the reactions below, including
structures for the respective products G and H.
NH
G
-NH₂
H
Transcribed Image Text:QUESTION 3 (a) Draw the orbital representation of imidazole. Briefly explain why imidazole is aromatic with particular reference to the nitrogen atom (s). (b) (c) 9 HN- 10 7 i) PhLi ii) (CH3)2CO iii) H3O* NH 5.2 Protonated triethylamine, pyridine, imidazole and pyrrole have pka values 9, 7, 5.2, -4.0, respectively. Give a clear explanation for the observed values. H,CO, Me,NH, HOẶC Draw chemical mechanisms for the reactions below, including structures for the respective products G and H. NH G -NH₂ H
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