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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

Draw the product formed when pyridine reacts with ethyl bromide.

What is the major product of the following reaction?

Rank the following compounds from easiest to hardest at removing a proton from its methyl substituent:

Name the following:


b.

c.

d.

Name the following:

a.

b.

c.
See all solutions

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