Question

What are two kinds of molecules or ions that commonly function as weak bases?

Short answer

Two kinds of molecules or ions that commonly function as weak bases are ammonia (NH3) and amines (R-NH2). Both have a lone pair of electrons on the nitrogen atom, allowing them to accept a proton (H+) and form an equilibrium with their conjugate acids in solution.

Step-by-step solution

Understand the characteristics of weak bases

Weak bases are substances that accept protons (H+) but do not fully dissociate in water. They have a moderate affinity for protons and form an equilibrium with their conjugate acids in solution.

Identify the first type of weak base - Ammonia

The first kind of molecule that commonly functions as a weak base is ammonia (NH3). Ammonia has a lone pair of electrons on the nitrogen atom, which can accept a proton (H+) to form the ammonium ion (NH4+). The reaction can be represented as follows: NH3(aq) + H2O(l) ⇌ NH4+(aq) + OH-(aq) Ammonia is a weak base because it does not fully dissociate in water and forms an equilibrium with its conjugate acid, ammonium.

Identify the second type of weak base - Amines

The second type of molecules that commonly function as weak bases are amines. Amines are organic compounds derived from ammonia (NH3) by replacing one or more of the hydrogen atoms with an alkyl or aryl group. Amines also have a lone pair of electrons on the nitrogen atom, allowing them to accept a proton (H+). Examples of amines include methylamine (CH3NH2), ethylamine (C2H5NH2), and aniline (C6H5NH2). The general reaction for an amine acting as a weak base can be represented as follows: R-NH2(aq) + H2O(l) ⇌ R-NH3+(aq) + OH-(aq) where R represents an alkyl or aryl group. Amines are weak bases because they do not fully dissociate in water and form an equilibrium with their conjugate acids. In conclusion, two kinds of molecules or ions that commonly function as weak bases are ammonia (NH3) and amines (R-NH2).

Key concepts

Ammonia

Ammonia, with the chemical formula \(NH_3\), is one of the most well-known examples of a weak base. It contains a nitrogen atom that carries a lone pair of electrons. This lone pair is crucial because it enables ammonia to accept protons \(H^+\) from water. This process leads to the formation of the ammonium ion \(NH_4^+\).

Despite its ability to accept protons, ammonia does not completely dissociate in solution. This means it establishes an equilibrium—a balance in the reaction—where both ammonia molecules and the ions \(NH_4^+\) and \(OH^-\) coexist in water. The equilibrium reaction can be written as:

• \( NH_3(aq) + H_2O(l) \rightleftharpoons NH_4^+(aq) + OH^-(aq) \)

Ammonia's characteristic as a weak base is due to this partial ionization.

Amines

Amines are organic compounds that can function as weak bases just like ammonia. Essentially, they are derivatives of ammonia where hydrogen atoms are replaced by alkyl or aryl groups. This gives them structures like \(R-NH_2\), where \(R\) is an alkyl or aryl group.

Like ammonia, amines also contain a lone pair of electrons on the nitrogen atom. This lone pair grants amines the ability to accept protons \(H^+\), forming an equilibrium with their conjugate acid, \(R-NH_3^+\). Some common examples of amines include methylamine \(CH_3NH_2\), ethylamine \(C_2H_5NH_2\), and aniline \(C_6H_5NH_2\). The general reaction is:

• \( R-NH_2(aq) + H_2O(l) \rightleftharpoons R-NH_3^+(aq) + OH^-(aq) \)

This equilibrium behavior is what categorizes amines as weak bases.

Proton Acceptance

Proton acceptance is a pivotal characteristic of weak bases like ammonia and amines. This ability stems from the presence of a lone pair of electrons on the nitrogen atom in these molecules.

When a weak base interacts with water, it accepts a proton \(H^+\). This process transforms the base into its conjugate acid form (e.g., \(NH_4^+\) for ammonia). The reaction also generates hydroxide ions \(OH^-\), which result in a basic solution.

However, because weak bases do not completely accept protons, they establish an equilibrium in solution. This means that the proton-accepting reaction is reversible and does not reach completion.

Equilibrium

The concept of equilibrium is vital in understanding how weak bases like ammonia and amines function. When a weak base is dissolved in water, it partially accepts protons \(H^+\). This results in a mixture of both the base and its conjugate acid coexisting in the solution.

In chemical terms, equilibrium is represented with a double-pointed arrow, indicating that the forward and reverse reactions occur at similar rates:

• \( NH_3(aq) + H_2O(l) \rightleftharpoons NH_4^+(aq) + OH^-(aq) \)
• \( R-NH_2(aq) + H_2O(l) \rightleftharpoons R-NH_3^+(aq) + OH^-(aq) \)

These reactions illustrate how weak bases do not fully ionize, instead forming a dynamic balance between reactants and products.

Conjugate Acids

When a weak base like ammonia or an amine accepts a proton, it transforms into its corresponding conjugate acid. For ammonia, this conjugate acid is the ammonium ion \(NH_4^+\). For amines, it takes on the general form \(R-NH_3^+\) where \(R\) is the alkyl or aryl group.

The formation of a conjugate acid is a critical aspect of acid-base reactions. It showcases the reversible nature of proton acceptance. Because the equilibrium isn't complete, the conjugate acid partly reverts back to the weak base, maintaining balance. This reversible reaction is a defining feature of weak bases in chemistry.