Chapter 14: Problem 39
Which is the stronger base, \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{N}\) or \(\mathrm{H}_{2} \mathrm{BO}_{3}^{-} ?\)
Short Answer
Expert verified
\(\left(\text{CH}_3\right)_3 N\) is the stronger base compared to \(\text{H}_2 \text{BO}_3^{-}\).
Step by step solution
01
Understand the Concept of Basicity
Basicity refers to a substance's ability to accept protons (H+ ions). In the Brønsted-Lowry theory, a base is a substance that can accept a hydrogen ion from an acid. Typically, a base with a negative charge is stronger than a neutral base, because the extra electron density can be used to bond to a proton. Also, the size, electronegativity, and the electron-donating or -withdrawing effects of substituents on the nitrogen in amines influence their basicity.
02
Compare the Molecular Structure
Trimethylamine \(\left(\text{CH}_3\right)_3 N\) is a tertiary amine with three electron-donating methyl groups that increase electron density on the nitrogen, making it a relatively stronger neutral base. The borate ion \(\text{H}_2 \text{BO}_3^{-}\) is a conjugate base of a weak acid (boric acid), and while it has a negative charge, it is not as basic because boron's electronegativity tends to hold onto electrons more tightly and the negative charge is delocalized over the structure, decreasing its availability to bond to a proton.
03
Identify the Weaker Acid Corresponding to Each Base
The acid corresponding to trimethylamine is a protonated trimethylamine, which is a weak acid. On the other hand, the acid corresponding to the borate ion is boric acid, also a weak acid. However, typically the strength of a conjugate base is inversely related to the strength of its corresponding acid. Between boric acid and protonated trimethylamine, boric acid is weaker, indicating that \(\text{H}_2 \text{BO}_3^{-}\) is the weaker base.
04
Determine the Stronger Base
Considering the electron-donating effects of the methyl groups and the positive effect they have on the basicity of trimethylamine, and that \(\text{H}_2 \text{BO}_3^{-}\) is the conjugate base of a weak acid but is not necessarily a strong base itself, trimethylamine \(\left(\text{CH}_3\right)_3 N\) is generally considered the stronger base compared to \(\text{H}_2 \text{BO}_3^{-}\).
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
Basicity
Basicity is a fundamental concept in acid-base chemistry, representing a substance's propensity to accept protons (H+ ions). Imagine a molecule eagerly waiting to grab a passing H+; that eagerness is its basicity. The more willing it is to snap up a proton, the stronger a base it is considered. A molecule's basicity can depend on various factors, such as charge, surrounding atoms, and the structure of the molecule itself.
For instance, bases that carry a negative charge are generally stronger than their neutral counterparts. This is because the negative charge indicates a surplus of electrons that are readily available to form a bond with the incoming proton. Structural aspects like the size of the molecule and the presence of electron-donating groups also impact how readily a base will accept a proton.
For instance, bases that carry a negative charge are generally stronger than their neutral counterparts. This is because the negative charge indicates a surplus of electrons that are readily available to form a bond with the incoming proton. Structural aspects like the size of the molecule and the presence of electron-donating groups also impact how readily a base will accept a proton.
Brønsted-Lowry Theory
Delving into the Brønsted-Lowry theory, we shift our focus to a more dynamic view of acids and bases. This theory presents a base as not merely a substance sitting idly by but as an active participant in the dance of proton exchange. In this framework, an acid is a proton donor and a base is a proton acceptor. They come together, exchange partners, and part ways, now transformed as conjugate pairs.
What's interesting is that the Brønsted-Lowry theory extends the definition of acids and bases beyond just those substances which dissolve in water to encompass a broader range of chemical species, including molecules that accept protons in non-aqueous environments. This emphasizes not just the features of the molecule but also the importance of context in acid-base reactions.
What's interesting is that the Brønsted-Lowry theory extends the definition of acids and bases beyond just those substances which dissolve in water to encompass a broader range of chemical species, including molecules that accept protons in non-aqueous environments. This emphasizes not just the features of the molecule but also the importance of context in acid-base reactions.
Conjugate Bases
In the intricate ballet of acid-base reactions, every base has a partner called a conjugate acid, and likewise, every acid has a corresponding conjugate base. After an acid donates its proton, what remains is the conjugate base. It's like the aftermath of a grand event; the acid has given away something precious, and the remaining part, the conjugate base, reflects that change.
Conjugate bases are interesting because their strength is inversely related to their corresponding acid's strength. Strong acids leave behind weak conjugate bases, while weak acids tend to have stronger conjugate bases. This inverse relationship is crucial when predicting the outcomes of chemical reactions and helps in understanding various chemical equilibria.
Conjugate bases are interesting because their strength is inversely related to their corresponding acid's strength. Strong acids leave behind weak conjugate bases, while weak acids tend to have stronger conjugate bases. This inverse relationship is crucial when predicting the outcomes of chemical reactions and helps in understanding various chemical equilibria.
Electronegativity
Electronegativity is like the measure of how much atoms hanker for electrons. It's a concept that helps us understand a variety of chemical properties, including basicity. Atoms with higher electronegativity are more adept at holding onto their electrons and are less inclined to be generous with them in forming new bonds.
When it comes to basicity, the higher the electronegativity of the atom holding the charge in a base, the lower the basicity tends to be. An atom that isn't so keen on sharing its electrons won't be as good at welcoming a proton. As such, in the competition for protons, bases composed of less electronegative atoms often have the upper hand.
When it comes to basicity, the higher the electronegativity of the atom holding the charge in a base, the lower the basicity tends to be. An atom that isn't so keen on sharing its electrons won't be as good at welcoming a proton. As such, in the competition for protons, bases composed of less electronegative atoms often have the upper hand.
Amine Basicity
Amines are compounds that feature nitrogen atoms which possess a lone pair of electrons, making them prime candidates for forming bonds with protons. The basicity of amines can be quite the conundrum as it is influenced by a host of factors such as the electronic properties of substituents attached to the nitrogen.
Substituents like the methyl groups in trimethylamine help to push electrons towards the nitrogen, making it more of a base. It's akin to giving someone a pair of boxing gloves; they become better fighters. The basicity increases because the nitrogen becomes more ready and willing to bond with a proton. However, every amine's story is unique, and predicting their basicity requires considering their molecular context in detail.
Substituents like the methyl groups in trimethylamine help to push electrons towards the nitrogen, making it more of a base. It's akin to giving someone a pair of boxing gloves; they become better fighters. The basicity increases because the nitrogen becomes more ready and willing to bond with a proton. However, every amine's story is unique, and predicting their basicity requires considering their molecular context in detail.