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Consider \(1.0 \mathrm{M}\) aqueous solutions of each of the following. Which solution is more basic? (a) Sodium cyanide \((\mathrm{NaCN})\) or sodium fluoride (NaF) (b) Sodium carbonate \(\left(\mathrm{Na}_{2} \mathrm{CO}_{3}\right)\) or sodium acetate \(\left(\mathrm{CH}_{3} \mathrm{CONa}\right)\) (c) Sodium sulfate \(\left(\mathrm{Na}_{2} \mathrm{SO}_{4}\right)\) or sodium methanethiolate \(\left(\mathrm{NaSCH}_{3}\right)\)

Short Answer

Expert verified
NaCN, Na鈧侰O鈧, and NaSCH鈧 are more basic.

Step by step solution

01

Understanding Basicity and Hydrolysis

In aqueous solution, salts may affect pH through hydrolysis reactions. A salt like sodium cyanide (NaCN) can hydrolyze to form CN鈦 ions, while sodium fluoride (NaF) can form F鈦 ions. Both are capable of hydrolysis, but the potential to increase pH (basicity) depends on the anion's base strength.
02

Comparing Anions' Basicity

For NaCN vs. NaF, we consider CN鈦 (from NaCN) and F鈦 (from NaF). Cyanide ion (CN鈦) is a stronger base than fluoride ion (F鈦) because CN鈦 can hydrolyze to produce more OH鈦 ions in water: \[ \text{CN}^- + \text{H}_2\text{O} \rightarrow \text{HCN} + \text{OH}^- \] This means NaCN will produce a more basic solution than NaF.
03

Assessing Carbonate and Acetate

For Na鈧侰O鈧 vs. CH鈧僀ONa, the anions are CO鈧兟测伝 (carbonate) and CH鈧僀OO鈦 (acetate). The carbonate ion (CO鈧兟测伝) is a stronger base than acetate (CH鈧僀OO鈦), as it can produce more OH鈦 ions through hydrolysis. Hence, Na鈧侰O鈧 will result in a more basic solution: \[ \text{CO}_3^{2-} + \text{H}_2\text{O} \rightarrow \text{HCO}_3^- + \text{OH}^- \text{ (multiple steps possible)} \]
04

Evaluating Sulfate and Methanethiolate

For Na鈧係O鈧 vs. NaSCH鈧, the anions are SO鈧劼测伝 (sulfate) and SCH鈧冣伝 (methanethiolate). The methanethiolate ion (SCH鈧冣伝) is a much stronger base than the sulfate ion (SO鈧劼测伝), thus NaSCH鈧 will result in a more basic solution. \[ \text{SCH}_3^- + \text{H}_2\text{O} \rightarrow \text{HSCH}_3 + \text{OH}^- \]
05

Conclusion of Comparisons

So, in all comparisons: (a) NaCN is more basic than NaF (b) Na鈧侰O鈧 is more basic than CH鈧僀ONa (c) NaSCH鈧 is more basic than Na鈧係O鈧

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Hydrolysis Reactions
Hydrolysis reactions play a crucial role in determining the basicity of solutions containing salts. When a salt dissolves in water, its ions can interact with water molecules. This process is known as hydrolysis. The main idea behind hydrolysis is the ability of anions from these salts to accept protons from water, leading to the generation of hydroxide ions \( \text{OH}^- \).
The presence of more hydroxide ions makes the solution more basic. For example, the cyanide ion \( \text{CN}^- \) can hydrolyze to produce hydroxide ions: \[ \text{CN}^- + \text{H}_2\text{O} \rightarrow \text{HCN} + \text{OH}^- \].
As you learn about different salts like sodium carbonate \( \text{Na}_2\text{CO}_3 \) or sodium methanethiolate \( \text{NaSCH}_3 \), focus on their anions' ability to undergo hydrolysis to comprehend the resulting basic nature of the solution.
Anions and Basicity
Anions, the negatively charged ions, significantly influence the basicity of an aqueous solution. The strength of a base is measured by its ability to generate hydroxide ions in water.
When comparing anions like \( \text{CN}^- \) from sodium cyanide and \( \text{F}^- \) from sodium fluoride, \( \text{CN}^- \) is stronger because it more readily produces \( \text{OH}^- \) through hydrolysis, hence making the solution more basic.
Similarly, the carbonate ion \( \text{CO}_3^{2-} \) from sodium carbonate is a stronger base compared to acetate ion \( \text{CH}_3\text{COO}^- \) from sodium acetate. For methanethiolate \( \text{SCH}_3^- \) and sulfate \( \text{SO}_4^{2-} \), methanethiolate's stronger base quality means it leads to more basic solutions.
Understanding which anions produce more hydroxide ions helps you determine the basicity of a solution.
Aqueous Solutions
Aqueous solutions are solutions where water is the solvent. In studying basicity, it is crucial to grasp how substances dissolve and interact in water.
When salts dissolve, they dissociate into their constituent ions. These ions may then interact with water, which can lead to hydrolysis as mentioned previously, affecting the overall pH of the solution.
For example, when sodium carbonate dissolves in water, its carbonate ions \( \text{CO}_3^{2-} \) may interact with water forming \( \text{OH}^- \), thus increasing the solution's basicity. Sodium methanethiolate behaves similarly, making its aqueous solution significantly basic. The behavior of these ions in water helps predict the pH levels of their solutions.
Organic Chemistry Problem Solving
Problem-solving in organic chemistry often requires a deep understanding of interactions in solutions. Identifying the hydrolysis capabilities of anions like cyanide and methanethiolate helps solve which solutions become more basic.
Using step-by-step approaches lets you break down complex interactions within the solution. For instance, by focusing on which anions produce more \( \text{OH}^- \), you can logically determine the basicity of different solutions such as sodium carbonate versus sodium acetate.
Additionally, understanding different reactions in aqueous solutions is key for problem-solving. Thus, practicing these problems boosts your analytical skills and understanding of organic chemistry concepts better, making the abstract ideas more tangible.

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Most popular questions from this chapter

In each of the following pairs, determine whether the two represent resonance contributors of a single species or depict different substances. If two structures are not resonance contributors, explain why. (a) \(: \ddot{\mathrm{N}}-\mathrm{N} \equiv \mathrm{N}: \quad\) and \(\quad: \mathrm{N}=\mathrm{N}=\mathrm{N}\) (c) \(: \ddot{\mathrm{N}}-\mathrm{N} \equiv \mathrm{N}: \quad\) and \(\quad: \ddot{\mathrm{N}}-\ddot{\mathrm{N}}-\ddot{\mathrm{N}}\) : (b) \(: \ddot{\mathrm{N}}-\mathrm{N} \equiv \mathrm{N}: \quad\) and \(\quad: \ddot{\mathrm{N}}-\mathrm{N}=\ddot{\mathrm{N}}\) :

Which is a stronger base, ethoxide \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}: \mathrm{)}\right.\) or tert-butoxide \(\left[\left(\mathrm{CH}_{3}\right)_{3} \mathrm{CO}:\right]\) ?

All of the hydrogens are bonded to carbon in both of the following. Write a Lewis formula that satisfies the octet rule for each. (a) Formaldehyde \(\left(\mathrm{CH}_{2} \mathrm{O}\right)\) (b) Hydrogen cyanide (HCN)

Nitrosomethane and formaldoxime both have the molecular formula \(\mathrm{CH}_{3} \mathrm{NO}\) and the connectivity CNO. All of the hydrogens are bonded to carbon in nitrosomethane. In formaldoxime, two of the hydrogens are bonded to carbon and one to oxygen. Write Lewis formulas for (a) nitrosomethane and (b) formaldoxime that satisfy the octet rule and are free of charge separation

Rank the following in order of decreasing concentration in a solution prepared by dissolving \(1.0\) mol of sulfuric acid in enough water to give \(1.0 \mathrm{~L}\) of solution. (It is not necessary to do any calculations.) $$ \mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{HSO}_{4}^{-}, \mathrm{SO}_{4}{ }^{2-}, \mathrm{H}_{3} \mathrm{O}^{+} $$

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