As shown below, pyridine -oxide G can undergo electrophilic aromatic substitution with electrophile E* to give product H. Pyridine N-oxide G can also undergo nucleophilic aromatic substitution with nucleophile Nuc¯ to give product I. Nuc H3C. E H3C. Nuc H3C. H G

As shown below, pyridine -oxide G can undergo electrophilic aromatic substitution with electrophile E* to give product H. Pyridine N-oxide G can also undergo nucleophilic aromatic substitution with nucleophile Nuc¯ to give product I. Nuc H3C. E H3C. Nuc H3C. H G

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.SE: Something Extra

Problem 68AP: Fill in the missing reagents a-e in the following scheme:

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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

Explain why pyridine N-oxide G can undergo electrophilic aromatic substitution with electrophile E+ to give product H. Include the resonance structures of pyridine N-oxide G to illustrate your answer.

As shown below, pyridine -oxide G can undergo electrophilic aromatic substitution with
electrophile E* to give product H. Pyridine N-oxide G can also undergo nucleophilic aromatic
substitution with nucleophile Nuc¯ to give product I.
Nuc
H3C.
E
H3C.
Nuc
H3C.
H
G

Definition Definition Organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Aromatic organic compounds, also called arenes, are an important class of hydrocarbons under the branch of organic chemistry.

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