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Chapter 19: Q11P (page 997)

Propose a mechanism for nitration of pyridine at the 4-position, and show why this orientation is not observed.

Short Answer

Expert verified

This orientation is not observed because electrophilic substitution reaction at 4-position is not stable. The intermediate formed by electrophilic addition at 4-position is less stable than that of 3-position.

Step by step solution

01

Introduction

In above mechanism, addition of an electrophile to pyridine in the 4 position results in the formation of three resonance structures of the intermediate form.

02

Justification

Electronic substitution at 4th position is not stable because 4-position carbon is not the most electron rich C atom in the pyridine ring. Whereas 3-position carbon is the most electron-rich C-atom, therefore pyridine undergoes electrophilic substitution at 3 position rather than 4 position.

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Most popular questions from this chapter

What would happen in the synthesis of sulfanilamide if the amino group were not protected as an amide in the chlorosulfonation step?

Basicity depends on availability of an electron pair to bond a proton. Correlate structural effects in these amines with their basicities.

(a) Explain this order:

Give the products expected when the following tertiary amines are treated with a peroxyacid and heated.

  1. N,N-dimethyl hexane-2-amine (b) N,N-diethyl hexane-2-amine

(c) cyclohexyl dimethyl amine (d) N-ethyl piperidine

Within each structure, rank the indicated nitrogens by increasing basicity.

The proton and 13C NMR spectra of a compound of formula C4H11N are shown here. Determine the structure of this amine, and give peak assignments for all of the protons in the structure.
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