Name: how solvents limit acid and base strength
Uploaded: 2024-04-04T10:51:20.000Z
Duration: 1 min 29 s
Channel: JoVE

酸塩基反応では、溶媒の共役塩基よりも強い塩基を用いると、溶媒が脱プロトン化されて共役塩基が生成されます。時間が経つにつれて、塩基は完全に消費され、溶媒よりも弱い酸を脱プロトン化できなくなります。
同様に、溶媒の共役酸よりも強い酸を使用すると、溶媒がプロトン化されて共役酸がより多く生成されます。最終的に、溶媒よりも弱い塩基をプロトン化するための酸は存在しません。
いずれの場合も、溶媒は、より強い塩基またはより強い酸が目的の化合物と反応するのを防ぎます。これが溶剤のレベリング効果です。 
酸塩基反応を成功させるためには、選択した溶媒が反応せずに反応を促進する必要があります。
説明のために、アミドイオンの水溶液を考えてみましょう。アミドイオンは水の共役塩基よりも強く、安定性が低いため、水を脱プロトン化し、より多くの水酸化物イオンの形成を促進します。
その結果、溶液には水酸化物イオンがほとんど含まれず、アミドイオンはほとんど含まれていません。水のレベリング効果により、アミドイオンは消費され、水よりも高いpK値を持つアセチレンのような化合物の脱プロトン化には利用できません。

利益相反は宣言されていません。

レベリング効果と非水酸塩基溶液

Leveling Effect

酸塩基の化学では、レベリング効果とは、溶液中の酸と塩基の強度に対して溶媒によって課される制限を指します。溶媒の共役塩基より強い塩基を使用すると、塩基が完全に消費されるまで溶媒が脱プロトン化され、弱い酸に対しては無効になります。逆に、溶媒の共役酸よりも強い酸は、酸が枯渇するまで溶媒をプロトン化し、より弱い塩基に対して無効になります。基本的に、溶媒はより強い酸や塩基を中和し、それらが他の化合物と意図したように反応するのを防ぎます。

たとえば、水 (水溶液) では、アミド イオンのような強塩基が水を脱プロトン化し、主に水酸化物イオンが形成され、アミド イオンはほとんど残りません。これにより、アミドイオンが水よりも高い pKa を持つアセチレンのような化合物を効果的に脱プロトン化することができなくなります。ただし、アンモニアのような塩基性溶媒を使用すると、アミドイオンがアセチレンを正常に脱プロトン化し、目的の反応を促進します。

要約すると、溶媒の酸性度は強塩基の有効性を制限し、溶媒の塩基性度は強酸の有効性を制限します。したがって、選択した溶媒は、それ自体が重大な反応を起こすことなく、酸塩基反応を促進するものでなければなりません。

酸塩基反応では、溶媒の共役塩基よりも強い塩基を使用すると、溶媒が脱プロトン化されて共役が生成されます...

Education

JoVE Core

Analytical Chemistry

分析化学

Unit 1

ユニット1

Acid–Base Titration

酸塩基滴定

KEY TERMS AND CONCEPTS

主要用語と概念

how solvents limit acid and base strength

The leveling effect explains how a solvent can limit acid and base strength in solution. In acid-base chemistry, the solvent sets a ceiling on how strong an acid or base can act. Stronger acids or bases may react with the solvent itself instead of with the intended compound.

When a base is stronger than the conjugate base of the solvent, it deprotonates the solvent first. A conjugate base is the species left after an acid loses a proton. This reaction keeps going until the stronger base is used up, so it becomes ineffective against weaker acids.

The same idea applies to acids. If an acid is stronger than the conjugate acid of the solvent, it protonates the solvent until the acid is depleted. As a result, the strong acid is no longer available to react with weaker bases.

Water is a common example. In aqueous solution, a strong base such as the amide ion removes a proton from water and mostly forms hydroxide ions. Very little amide ion remains, so it cannot efficiently deprotonate compounds like acetylene, which has a higher pKa than water.

A more basic solvent can change the outcome. In ammonia, the amide ion can deprotonate acetylene successfully. This example shows that the chosen solvent must allow the acid-base reaction to happen without reacting so strongly itself that it blocks the desired result.

How Solvents Limit Acid and Base Strength

how-solvents-limit-acid-and-base-strength

acid&#8211;base titration: overview

Titration Curves and pH Changes

Acid-base titration uses a known acid or base to find the concentration of an unknown solution. A base can titrate an acid, or an acid can titrate a base. As titrant is added little by little, the pH changes in a predictable way. The pH change is shown on a titration curve. A titration curve plots how the pH of the solution changes as more titrant is added. Scientists use this curve to follow the progress of the titration and to identify the endpoint, which is the point used to stop the...

titration of a strong acid with a strong base

titration-of-a-strong-acid-with-a-strong-base

pH Changes in Strong Acid-Base Titration

pH changes in a strong acid-strong base titration depend on the amount of leftover hydronium or hydroxide ions. A strong acid such as hydrochloric acid fully dissociates in water. That gives the solution hydronium ions and chloride ions, so the starting pH is low. When sodium hydroxide is added, it neutralizes hydronium ions. As more base is added, the concentration of hydronium ions falls and the pH rises. At the equivalence point, the hydronium ions have been neutralized and the solution is...

titration of a weak acid with a strong base

titration-of-a-weak-acid-with-a-strong-base

Weak Acid Titration Curve and pH Stages

Weak acid titration with a strong base changes pH in clear stages. The acid in this example is acetic acid, and the base is sodium hydroxide. Each stage uses a different pH calculation method. At the start, the pH of the weak acid is found with its dissociation constant, Ka, and an ICE table. An ICE table tracks the initial, change, and equilibrium amounts of the acid. This step describes the acid before much base is added. As sodium hydroxide is added, a buffer forms. A buffer is a solution...

titration of a weak base with a strong acid

titration-of-a-weak-base-with-a-strong-acid

Ammonia Titration Curve with HCl

Ammonia titration with hydrochloric acid shows how a weak base behaves as acid is added. The curve is the mirror image of a weak acid titrated with a strong base. In this case, ammonia acts as the weak base, and hydrochloric acid acts as the strong acid. The starting pH of 50 mL of 0.1 M ammonia is found with an ICE table and the Kb value. That calculation gives an initial pH of 11.11. As hydrochloric acid is added, the pH begins to fall. After 25 mL of 0.1 M hydrochloric acid is added, the...

titration of a weak acid with a weak base

titration-of-a-weak-acid-with-a-weak-base

Finding the Endpoint in Weak Acid–Base Titration

Weak acid and weak base titration is used to follow how pH changes as base is added. In this kind of titration, both the acid and the base dissociate only partly. The titration curve shows a slow, gradual pH change instead of a sharp jump. A common example is the titration of acetic acid with ammonia. During the reaction, these two species form ammonium acetate and water. Because the pH changes so gradually, there is no simple indicator that shifts color sharply at the equivalence point. One...

solution composition during acid/base titrations

solution-composition-during-acidbase-titrations

Acetic Acid Buffer Changes in Titration

Acetic acid buffer changes during a weak acid–strong base titration. When acetic acid is titrated with sodium hydroxide, the reaction forms water and the conjugate base of the acid, sodium acetate. The mixture of acetic acid and sodium acetate acts as a buffer, which helps show how solution makeup shifts during the titration. The relative amounts of acetic acid and acetate ions are tracked with α values. Here, α0 represents the equilibrium concentration of acetic acid, and α1 represents the...

mixtures of acids

Finding pH in Acid Mixtures

Finding pH in acid mixtures depends on the acids present and their dissociation constants. When a solution contains two acids, the pH can be found by choosing the method that matches their relative strengths. The key idea is that the stronger acid often controls the hydronium ion level, which is the amount of H3O+ in solution. In a mixture of a strong acid and a weak acid, the strong acid dissociates completely. It becomes the main source of hydronium ions in the solution. The weak acid...

titration in nonaqueous solvents

Nonaqueous Solvents for Sharper Titration Endpoints

Nonaqueous solvents can make acid-base titrations easier to read by giving sharper endpoints. Most acid-base titrations are done in water, but water can compete with weak acids or bases for proton donation or acceptance. That competition can blur the titration curve and make the endpoint less clear. Water also changes the partial ionization of weak acids and bases. For example, water can accept a proton from acetic acid to form hydronium and acetate ions. The hydronium ion is a stronger acid...

titration of polyprotic base with a strong acid

titration-of-polyprotic-base-with-a-strong-acid

Carbonate Buffering in Acid Titration

The titration of sodium carbonate with hydrochloric acid shows how a polyprotic base reacts in stages. A polyprotic base can accept more than one proton, so its titration curve has two equivalence points. These points mark where one form has been fully changed into the next. At the first equivalence point, carbonate ions are completely converted to bicarbonate ions. The region before this point is the carbonate/bicarbonate buffer. In this buffer region, both forms are present in the solution. <br...

titration of polyprotic acids with a strong base

titration-of-polyprotic-acids-with-a-strong-base

Polyprotic Acid Titration Curve Features

Polyprotic acid titration curves show how acids with more than one ionizable proton react with a strong base. Each proton is released in a separate step. Each step has its own dissociation constant, or Ka, and each later Ka is weaker than the one before it. When a polyprotic acid such as sulfurous acid is titrated with sodium hydroxide, the base first neutralizes the first ionizable proton. This forms an intermediate species, such as hydrogen sulfite ions. The first part of the curve looks...

composition of polyprotic acid solutions as a function of ph

composition-of-polyprotic-acid-solutions-as-a-function-of-ph

Polyprotic Acid Titration Fractions at Each pH

Polyprotic acid titration shows how the main species in solution change as pH changes. In a compound of the form H2M, there are two ionizable protons. That means the titration with a base produces two equivalence points on the curve. As base is added, three species can be present in the solution: H2M, HM−, and M2−. Their amounts are shown as fractions called α0, α1, and α2. These alpha values track how much of each form is present at different stages of the titration. At the start of the...

buffers: overview

Buffers and pH Stability

Buffers help keep the pH of a solution stable when small amounts of acid or base are added. They are made from a weak acid and its conjugate base, or from a weak base and its conjugate acid. This balance lets the solution resist large pH changes until the buffer capacity is exceeded. One common buffer uses acetic acid and sodium acetate. Here, CH3COOH acts as the weak acid and CH3COONa provides its salt. Another buffer uses ammonia and ammonium chloride, written as NH3 and NH4Cl. These...

buffers: buffer capacity

Buffer Capacity and pH Resistance

Buffer capacity describes how well a buffer resists changes in pH. It is a quantitative measure, so it tells how much acid or base a one-liter buffer solution can take before its pH shifts by 1 unit. In the equation, beta is the buffer capacity, while Ca and Cb represent the moles of acid and base added. The term dpH means the change in pH. A graph of pH versus the moles of base added to a weak acid with a pKa of 5 shows how buffering works as more base is added. Taking the derivative of that...

leveling effect

The leveling effect explains how a solvent can limit acid and base strength in solution. In acid-base chemistry, the solvent sets a ceiling on how strong an acid or base can act. Stronger acids or bases may react with the solvent itself instead of with the intended compound. When a base is stronger than the conjugate base of the solvent, it deprotonates the solvent first. A conjugate base is the species left after an acid loses a proton. This reaction keeps going until the stronger base is...

key terms and concepts

Learn how the leveling effect in acid-base chemistry limits strong acids and bases in water and other solvents, with clear examples for high school students.

How Solvents Limit Acid and Base Strength | JoVE K12

JoVE Core 分析化学 は、複雑な化学原理をアニメーションで視覚化することで、SI 単位から NMR 分光法を含むトピックをよりわかりやすくします。実験を撮影した実写動画では、これらの概念が世界中の研究所でどのように応用されているかを取り上げています。

How Solvents Limit Acid and Base Strength

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