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2.22

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Organic Chemistry
Found in: Page 75

Short Answer

The C-H bond in acetone, , has a of 19.2. Draw two resonance structures for its conjugate base.

Then, explain why acetone is much more acidic than propane, .

Acetone is more acidic than propane as its conjugate base is resonance stabilized.

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Step by Step Solution

Resonance structures

The structures that depict the bonding/delocalization of electrons in a molecule are named resonance structures.

The higher the number of resonance structures of a molecule, the higher will be its stability.

Conjugate base and the strength of the acid

The species obtained after removing or losing a proton from a molecule (acid) is its conjugate base.

The acid’s strength can be predicted by considering the stability of its conjugate base. The higher is the stability of the conjugate base, the greater is the strength of the acid.

Stability of the conjugate base

The removal of a hydrogen atom from acetone generates its conjugate base.

Resonance structures of the conjugate base of acetone

The conjugate base of acetone has two resonance structures. The removal of a proton from propane yields its conjugate base (propyl anion).

The conjugate base of propane

The propyl anion has only one Lewis structure, and it does not participate in resonance.

The conjugate base of acetone is more resonance stabilized than that of propane. Thus, acetone is more acidic than propane.

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