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Chapter 19: Q24P (page 946)

Which of the following compounds is easier to decarboxylate?

or

Short Answer

Expert verified

The reactivity of pyridine is low towards an electrophilic substitution reaction because of the presence of an electron withdrawing nitrogen atom.

A pyridine undergoes such a reaction under vigorous conditions. It is more reactive towards a nucleophilic substitution reaction.

Step by step solution

01

Reactivity of pyridine 

The reactivity of pyridine is low towards an electrophilic substitution reaction because of the presence of an electron withdrawing nitrogen atom.

A pyridine undergoes such a reaction under vigorous conditions. It is more reactive towards a nucleophilic substitution reaction.

02

Identifying the compound that is easier to decarboxylate

Compounds

The compound shown on the right is easier to decarboxylate as the electrons left behind when the carbon dioxide is removed can be delocalized into nitrogen, generating a stable neutral species because of the proton donation to nitrogen.

Decarboxylation of the compound on the right

The electrons left behind when the other compound loses the carbon dioxide cannot be delocalized.

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Most popular questions from this chapter

Question:

a.Propose a mechanism for the following reaction:

b.What other product is formed in this reaction?

Pyrrole reacts with excess para-(N,N-dimethylamino)benzaldehyde to form a highly colored compound. Draw the structure of the colored compound.

Draw the product of each of the following reactions:

a.

b.

C.

d.

a. Draw resonance contributors to show why pyridine-N-oxide is more reactive than pyridine toward electrophilic aromatic substitution.

b. At what position does pyridine-N-oxide undergo electrophilic aromatic substitution?

What starting materials are required to synthesize the following compounds, using the Fischer indole synthesis?

a.

b.

c.
See all solutions

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