How Do H3CC(=O)CH2CH3 and HCO2H Behave as Lewis Acids and Bases?

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In summary, H3CC(=O)CH2CH3 could act as either a Lewis Acid or Lewis Base, depending on its tautomerization state. HCO2H, on the other hand, is a Lewis Acid due to the ability of its acidic proton to accept an electron pair.
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Homework Statement


Is H3CC(=O)CH2CH3 more likely to act as a Lewis Acid or Lewis Base? Explain your choice.

Same for HCO2H (formic acid)

Homework Equations


N/A

The Attempt at a Solution


Since a Lewis Base donates electron pairs, and the oxygen in H3CC(=O)CH2CH3 has two lone pairs, I reasoned that H3CC(=O)CH2CH3 is a Lewis Base.

I know HCO2H should be a Lewis Acid because it is formic acid, but I don't know how the molecule would accept an electron pair.
 
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crm07149 said:
I know HCO2H should be a Lewis Acid because it is formic acid, but I don't know how the molecule would accept an electron pair.
The acidic proton accepts an electron pair. This is usually followed by the proton leaving to attach to the electron pair donor.

crm07149 said:
Since a Lewis Base donates electron pairs, and the oxygen in H3CC(=O)CH2CH3 has two lone pairs, I reasoned that H3CC(=O)CH2CH3 is a Lewis Base.
This answer is fine, though I will point out that methyl ethyl ketone can also display weak acidity through keto-enol tautomerization. Essentially, the proton on the hydroxyl group in the enol form of this molecule is slightly acidic. So this molecule can actually be either a Lewis acid or a Lewis base.
 

Related to How Do H3CC(=O)CH2CH3 and HCO2H Behave as Lewis Acids and Bases?

What is a Lewis Acid?

A Lewis acid is a chemical species that can accept a pair of electrons from another species, known as a Lewis base. This results in the formation of a coordinate covalent bond. Lewis acids are also known as electron pair acceptors.

What is a Lewis Base?

A Lewis base is a chemical species that can donate a pair of electrons to another species, known as a Lewis acid. This also results in the formation of a coordinate covalent bond. Lewis bases are also known as electron pair donors.

What is the difference between a Lewis Acid and a Bronsted-Lowry Acid?

The main difference between a Lewis acid and a Bronsted-Lowry acid is their definition of acidity. A Lewis acid is defined as an electron pair acceptor, while a Bronsted-Lowry acid is defined as a proton (H+) donor. This means that all Bronsted-Lowry acids are also Lewis acids, but not all Lewis acids are Bronsted-Lowry acids.

What are some examples of Lewis Acids and Bases?

Some common examples of Lewis acids include metal ions such as Fe3+, Al3+, and Cu2+. Examples of Lewis bases include ammonia (NH3), water (H2O), and fluoride ion (F-). In general, any species that has a lone pair of electrons available for donation can act as a Lewis base.

Why are Lewis Acids and Bases important in chemistry?

Lewis acids and bases play a crucial role in many chemical reactions, including acid-base reactions, coordination compounds, and organic reactions. They also help to explain the fundamental principles of chemical bonding and the behavior of various chemical species. Understanding Lewis acids and bases is essential for many fields of chemistry, including biochemistry, environmental chemistry, and materials science.

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