Practice Problem: Site of Protonation on a Weak Base

The video tutorial explains the reaction of acetamide, a weak base, with hydrochloric acid, a strong acid. It covers the Bronsted-Lowry acid-base theory, focusing on proton transfer. The tutorial discusses potential protonation sites on the acetamide molecule, emphasizing the role of lone pairs on nitrogen and oxygen atoms. It concludes with an analysis of resonance stabilization, highlighting why protonation occurs at the carbonyl position due to increased stability.

What is the role of acetamide in its reaction with hydrochloric acid?

• It acts as a neutral compound.

• It acts as a strong acid.

• It acts as a catalyst.

• It acts as a weak base.

According to the Bronsted-Lowry theory, what is the role of hydrochloric acid in the reaction with acetamide?

• Proton donor

• Electron donor

• Proton acceptor

• Electron acceptor

Which atom in acetamide is initially considered for protonation?

• Sulfur atom

• Nitrogen atom

• Hydrogen atom

• Carbon atom

What is the key feature of the structure when the carbonyl oxygen in acetamide is protonated?

• It is resonance stabilized.

• It becomes a strong acid.

• It loses all lone pairs.

• It forms a covalent bond with nitrogen.

Why is the protonation of the carbonyl oxygen in acetamide more stable?

• Because it removes all formal charges.

• Because it increases the energy of the molecule.

• Because it forms a new molecule.

• Because it is resonance stabilized, lowering the energy.