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Chapter 23: Q13 P (page 1085)

Which compound is more easily decarboxylated?

Short Answer

Expert verified

Compound 2 is much easier to decarboxylate than compound 1 because of resonance.

Step by step solution

01

Resonance

Resonance is the phenomenon of delocalization of pi-electron in a structure. Resonance provides more stability to a molecule.

02

Stability of compound 1

The first compoundis given below here it can be seen that on elimination the electron left behind are not present in resonance and are localized on carbon which is less electronegative atom and hence this makes the decarboxylation difficult to occur

Compound 1

03

Stability of compound 2

The second compoundis given below here it can be seen that on elimination the electron left behind are delocalized to positively charged nitrogen in ring by resonance and nitrogen is highly electronegative atom and hence this makes the decarboxylation easy to occur.

Compound 2

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