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2.23

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Organic Chemistry
Found in: Page 75

Short Answer

Acetonitrile has a of 25, making it more acidic than many other compounds having only C-H bonds. Draw Lewis structures for acetonitrile and its conjugate base. Use resonance structures to account for the acidity of acetonitrile.

Acetonitrile is more acidic than other compounds involving carbon-hydrogen (C-H) bond as its conjugate base is resonance stabilized.

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Step by Step Solution

Lewis structures

Structures that describe the atoms and the bonds between the atoms in a molecule are called lewis structures.

Lewis structure of acetonitrile

Acetonitrile consists of carbon, hydrogen, and nitrogen atoms.The number of valence electrons in carbon, hydrogen, and nitrogen are 4, 1, and 5, respectively.

Place the atoms according to their best possible arrangement and assign the valence electrons as bonds between every two atoms.

Check whether the octet of each atom is satisfied or not. If not, then assign the remaining valence electrons as lone pairs or bonds.

Resonance structure of acetonitrile

Conjugate base

The removal of hydrogen atom/proton from a molecule yields its conjugate base.

The conjugate base of acetonitrile is shown below.

The conjugate base of acetonitrile

The conjugate base of acetonitrile participates in resonance, and the negative charge can exist on both carbon and nitrogen atoms.

Acidity of acetonitrile

The higher the stability of the conjugate base of an acid is, the higher or more is its acid strength.

The conjugate base of acetonitrile is resonance stabilized. Hence, acetonitrile is a stronger acid than other compounds having carbon-hydrogen (C-H) bonds.

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