Chemistry - GOC Question with Solution | TestHub

ChemistryGOCAcid BaseMedium2 minQB
ChemistryMediumsingle choice

Compare the two protons H₁ and H₂ shown in the following compound and identify which proton is more acidic.

structure

Options:

Answer:
D
Solution:

Removing H₁ puts the negative charge on the amino nitrogen : structure

Removing H₂ puts the negative charge on the amide nitrogen : structure

In the first conjugate base the charge is localised on nitrogen. In the second, the charge is delocalised by resonance over the amide nitrogen and the carbonyl oxygen. A delocalised charge is more stable, so the second conjugate base wins and the amide N-H proton H₂ is more acidic.

Stream:JEESubject:ChemistryTopic:GOCSubtopic:Acid Base
⏱ 2mℹ️ Source: QB

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