Tuesday, May 30, 2023

How To Determine Strong Acids And Bases Organic Chemistry

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Strong And Weak Bases

Acids and Bases – Basic Introduction – Organic Chemistry

The issue is similar with bases: a strong base is a base that is 100% ionized in solution. If it is less than 100% ionized in solution, it is a weak base. There are very few strong bases ) any base not listed is a weak base. All strong bases are OH compounds. So a base based on some other mechanism, such as NH3 , will be a weak base.

Example \: Identifying Strong and Weak Acids and Bases

Identify each acid or base as strong or weak.

How Do We Quantify Acid Strength

Saying that one acid is strong while the other one is weak is a little bit of handwaving. So, is there a way how we can quantify the strong and the weak using some sort of numeric value?

We use the acid dissociation constants for this purpose. By the definition, the dissociation constant for an acid equals to the ratio of the product concentrations over the concentration of reagents.

Lets look at it on the example of dissociation of HCN:

Hydrogen cyanide is a weak acid and only dissociates partially. The reagent in this case is the acid itself . While the products are the proton and the cyanide anion . We now can get the expression of the dissociation constant by putting the concentrations of these species into the equation for Ka. And since the hydrogen cyanide is a weak acid, well have only a very small quantity of our products. This results in a very small Ka value.

How To Determine A Strong Base Organic Chemistry

Equilibrium & Acid Base by Sarah Wegwerth. Review of general chemistry concepts for organic chemistry.

TL DR Version In many ways organic chemistry is very different from general chemistry. However, there are things that you learned in general chemistry that are essential for grasping organic chemistry concepts. In particular, we will be reviewing equilibrium and how it applies to acid-base reactions. Often these concepts are reviewed during the first semester of organic chemistry and heavily used second semester. If you feel like you could use a quick review then keep reading. The theme for this post: Lower energy is favorable. NEW! Super Short Version EquilibriumAt equilibrium the rate of the forward and reverse reaction is equalA generic equilibrium reactionMeaning 1 reactants are going to products AND products are going to reactants at the same rate2 the concentrations of reactants and products remains constantThis does NOT mean the concentration of reactants = concentration of productsConcentrations are used to calculate the equilibrium constant Remember our theme: lower energy is favorable.

Video advice: Which molecule is more basic? Organic Chemistry Part 1

Which molecule is more basic?

Video advice: Acids and Bases Basic Introduction Organic Chemistry

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How To Read The Ka Values

Since the Ka is a mathematical expression for the state of equilibrium, it is quite easy to interpret. If the Ka value is small, we dont have much of our products. No products means no dissociation. No dissociation means weak acid. Likewise, a large Ka value means tons of products. Tons of products means complete dissociation. Complete dissociation means strong acid. Quite straightforward.

The issue with the Ka values is that those are generally very ugly numbers that are difficult to work with, yet aloneremember. So, typically, we are going to be using the pKa values instead. By definition, the pKa value is a negative logarithm of the Ka value. It doesnt have any physical meaning outside of the convenience.

The important feature of the pKa scale is that it is inverted compared to the Ka scale. Thus, strong acids will have a negative pKa values, while weak acids will have positive pKa values.

Acids And Bases In Organic Chemistry

How To Use a pKa Table

Acids and bases are crucial when it comes to organic chemistry.

Not those crazy ice charts and pKa calculations. At the organic chemistry level you will be asked to differentiate and rank acids and bases by looking at their molecular structure and comparing their reactions.

This shows up early in Orgo 1 when you learn the material, then again when ranking the reactivity of bases in elimination reactions, and again in Orgo 2 when studying stability of complex molecules.

As an orgo tutor I am often frustrated by the manner in which this material is taught. My students come to me all confused with data they memorized but don’t understand. And so I created what I hope is a complete resource to help you really GET acids and bases.

Be sure to watch each video to learn the information with a concept/trend focus. If you’d like to see this subject with more focus on the math, see my MCAT Acid/Base Tutorial Series. Then download my FREE Acid Base Cheat Sheet to take your studies on the go. And when you feel ready, see how you do on my Acid Base Practice Quiz.

Don’t forget to grab the Strong Acid/Base Mini Cheat Sheet.

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Acid And Base Ionization Constants

The relative strength of an acid or base is the extent to which it ionizes when dissolved in water. If the ionization reaction is essentially complete, the acid or base is termed strong if relatively little ionization occurs, the acid or base is weak. As will be evident throughout the remainder of this chapter, there are many more weak acids and bases than strong ones. The most common strong acids and bases are listed in Figure 14.6.

The relative strengths of acids may be quantified by measuring their equilibrium constants in aqueous solutions. In solutions of the same concentration, stronger acids ionize to a greater extent, and so yield higher concentrations of hydronium ions than do weaker acids. The equilibrium constant for an acid is called the acid-ionization constant, Ka. For the reaction of an acid HA:

O + and Aâ relative to the concentration of the nonionized acid, HA, in an equilibrium mixture, and the stronger the acid. An acid is classified as âstrongâ when it undergoes complete ionization, in which case the concentration of HA is zero and the acid ionization constant is immeasurably large . Acids that are partially ionized are called âweak,â and their acid ionization constants may be experimentally measured. A table of ionization constants for weak acids is provided in Appendix H.


How To Determine The Stronger Acid

In Organic Chemistry, acids and bases is really quite qualitative. Were often looking at whether a compound is even acidic or basic at all. Or if we compare two compounds, which one is more acidic or more basic or which part of an organic compound is acidic or basic? Watch the video below to find out!

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Effect Of Molecular Structure On Acid

Binary Acids and Bases

In the absence of any leveling effect, the acid strength of binary compounds of hydrogen with nonmetals increases as the H-A bond strength decreases down a group in the periodic table. For group 17, the order of increasing acidity is HF < HCl < HBr < HI. Likewise, for group 16, the order of increasing acid strength is H2O < H2S < H2Se < H2Te.

Across a row in the periodic table, the acid strength of binary hydrogen compounds increases with increasing electronegativity of the nonmetal atom because the polarity of the H-A bond increases. Thus, the order of increasing acidity across the second row is CH4< NH3< H2O < HF across the third row, it is SiH4< PH3< H2S < HCl .

Acid And Base Strength

How To Memorize The Strong Acids and Strong Bases

For a reaction to be in equilibrium a transfer of electrons needs to occur. The acid will give an electron away and the base will receive the electron. Acids and Bases that work together in this fashion are called a conjugate pair made up of conjugate acids and conjugate bases. HA+ZA+HZ+

  • Brønsted-Lowery Definition
  • In 1923, chemists Johannes Brønsted and Martin Lowry independently developed definitions of acids and bases based on compounds abilities to either donate or accept protons . Here, acids are defined as being able to donate protons in the form of hydrogen ions whereas bases are defined as being able to accept protons. This took the Arrhenius definition one step further as water is no longer required to be present in the solution for acid and base reactions to occur.

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    What Do You Do When Trying To Assess Multiple Factors That Affect Acidity

    Whenever the issue of negative charge stability comes up, so should the issue of acidity and basicity. These items are woven together.

    So far Ive just talked about trends. But what do you do when you need to compare the acidity of two species that arent related by a trend, like, propanol and H2S? How do you proceed?

    In this case we are going to resort to the results of experimental measurements, and in the next post Ill start to discuss how we do that.

    How Do You Distinguish Between A Strong Acid And A Strong Base

    2:334:118.3.3 Distinguish between strong and weak acids and bases – YouTubeYouTubeStart of suggested clipEnd of suggested clipSo this could be the strong acid or the strong base they both dissociate completely in solutionMoreSo this could be the strong acid or the strong base they both dissociate completely in solution giving a high concentration of ions which conducts the electricity on the right.

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    Acidbase Reaction Direction And Position Of Equilibrium

    Acid base reactions begin because of electrostatic interactions, but the extent to which the reaction proceeds depends on the relative Gibbs free energy of the reactants and products, that is, the overall Gibbs free energy change for the reaction. This is a subtle but important point: the reaction does not occur because the products are more stable, it occurs because there is an attractive force between two reactants that have polar structures, As we will see, we can predict the relative amounts of reactants and products in a mixture , based both on an understanding of molecular structures and by comparing their pKa.

    AcidStrength: The strength of an acid, that is the degree to which it donates H+ to other molecules, depends on a number of factors including, obviously, the strength of the base it reacts with. Acid and base strengths are usually reported using water as the solvent , so that acid strengths can be compared directly. Since biological reactions take place in aqueous solution we will be able to extend our understanding of simple acid base reactions to much more complex ones as we move forward.

    The reaction for any acid HA is:

    HA + H2O H3O+ + A

    We can estimate the extent of the reaction by determining the equilibrium constant Ka.

    Ka = /

    Some representative Ka and pKa values.


    ~1055 55

    memorize a few important approximate pKa values

    Questions to answer:

    CH3NH3+ + H20

    Organic Acids and Bases

    Questions to answer:

    Organic Bases

    NH3 + H2O NH4+ + OH

    What Determines The Strength Of A Base

    How To Use a pKa Table

    Just as we did with acids in the last section, this section will focus on what determines the strength of a base.

    To determine the basicity of a molecule, one must look at the atom in question however, we now want to focus on how much electron density is focused on this atom. The less stable the molecule is , the more it will want to give some of its electron density by accepting a proton therefore, the strongest base will be the one with the highest energy electrons .

    All of the conditions presented in the Determining the Acidity section are just reversed:

  • The less electronegative an atom , the more basic it likely is.
  • If electron density can be delocalized by resonance, the molecule is a weaker base as it is less interested in losing electrons and accepting a proton. Resonance weakens a base because it makes a molecule more stable.
  • An electronegative atom might reduce basicity due to inductive effects. This is because such an atom stabilizes electron density, reducing the need for sharing it with a proton.
  • This leads to an important point: acids and bases are inverses. If a molecule is a strong acid, then it is a weak base. If it is a weak acid, then it is a strong base.

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    Acids Are Proton Donors And Bases Are Proton Acceptors

    For a reaction to be in equilibrium a transfer of electrons needs to occur. The acid will give an electron away and the base will receive the electron. Acids and Bases that work together in this fashion are called a conjugate pair made up of conjugate acids and conjugate bases.HA+ZA+HZ+

    A stands for an Acidic compound and Z stands for a Basic compound

    • A Donates H to form HZ+.
    • Z Accepts H from A which forms HZ+
    • A becomes conjugate base of HA and in the reverse reaction it accepts a H from HZ to recreate HA in order to remain in equilibrium
    • HZ+ becomes a conjugate acid of Z and in the reverse reaction it donates a H to A recreating Z in order to remain in equilibrium

    Calculating The Ph Of A Strong Acids And Bases Examples

    Q1. Suppose you have a 0.1M solution of HCl. Calculate its pH.

    HCl + H2O H3O+ + Cl

    Since hydrochloric acid is strong, we get 100% dissociation. O.1M is also the concentration of hydronium ions.

    To calculate the pH, plug in 0.1M into the pH equation:

    pH = -log = -log = 1

    Q2. Suppose you have a 0.1M solution of NaOH. Calculate its pH.

    NaOH + H2O Na+ + OH

    Since sodium hydroxide is a strong base, we get 100% dissociation. O.1M is also the concentration of hydroxide ions.

    To calculate the pH, plug in 0.1M into the pOH equation:

    pOH = -log = -log = 1

    Then, use the following equation to solve for pH:

    pH + pOH = 14

    pH = 14 pOH = 14 1 = 13

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    New Super Short Version :


    At equilibrium the rate of the forward and reverse reaction is equal


    1 â reactants are going to products AND products are going to reactants at the same rate

    2 â the concentrations of reactants and products remains constant

    This does NOT mean the concentration of reactants = concentration of products

    Concentrations are used to calculate the equilibrium constant

    Remember our theme: lower energy is favorable. The side of lower energy is favored at equilibrium. By favored we mean there is a higher concentration.

    This meansâ¦

    Acid Base Chemistry

    Acid base reactions are reversible and therefore equilibrium reactions.

    With acid base reactions we focus on the extent to which theACID is deprotonated to the conjugate acid . Therefore, as the equivalent to the equilibrium constant, we look at the Ka.

    To eliminate the need for scientific notation we then convert the Ka to the pKa

    Because of the -log function, now the smaller the pKa value the more the products are favored. This means the stronger the acid the smaller the pKa value.

    In short,

    · The smaller the pKa the stronger the acid

    · Acid-base equilibriums favor the side with the acid with a larger pKa

    Arrhenius Acids And Bases

    Acids and Bases – Basic Introduction – Chemistry

    According to the Arrhenius definition, proposed by the Swedish physical chemist Svante Arrhenius, an acid is a donor of a proton while the base is a donor of the hydroxyl ion . A typical example of an Arrhenius acid is something like hydrochloric acid . While a typical example of an Arrhenius base is something like sodium hydroxide . Once those species dissociate, HCl gives H+ into the solution, while NaOH gives off the OH ion.

    The problem with this definition is that it is extremely limited in its scope and is only applicable towards aqueous solutions. In organic chemistry, however, we rarely deal with aqueous solutions. Thus, this definition doesnt work for our purposes.

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    Examples Of The Pka Values And How We Can Use Them

    Lets look at a few species so we can see how the Ka and the pKa values compare to each other.

    On this picture we have methanol, acetic acid, methanethiol, and methylamine. Next to each of these species we have their corresponding Ka and pKa values. By doing a quick comparison of those numbers, we can see that the acetic acid the strongest acid among these molecules. Meanwhile, the amine species at the very end is the weakest acid with the lowest Ka value and, correspondingly highest pKa value. Thus, if we wanted to, for instance, rank those molecules according to their acid strength from the weakest to the strongest, wed get the following:

    Questions like this one are fairly common on exams, so you may want to do some extra practice to be all prepared on the test.

    The Most Common Strong Acids And Bases And Some Examples Of Weak Acids And Bases Together With Definition Of Strong And Weak Acids And Bases

    A strong acid or a strong base completely ionizes in a solution. In water, one mole of a strong acid HA dissolves yielding one mole of H+ and one mole of the conjugate base, A. Essentially, none of the non-ionized acid HA remains.

    Strong acid: HA + H2O A- + H3O+

    Strong base: BOH + H2O B+ + OH-

    Examples of strong acids and bases are given in the table below. In aqueous solution, each of these essentially ionizes 100%.

    A weak acid or a weak base only partially dissociates. At equilibrium, both the acid and the conjugate base are present in solution

    Weak acid: AH + H2O A- + H3O+

    Weak base: BOH + H2O B+ + OH- or

    B + H2O BH+ + OH-

    Examples of weak acids and bases are given in the table below.Stronger acids have a larger acid dissociation constant and a smaller logarithmic constant than weaker acids. The stronger an acid is, the more easily it loses a proton, H+.

    Two key factors that contribute to the ease of deprotonation are the polarity of the HA bond and the size of atom A, which determines the strength of the HA bond. Acid strengths also depend on the stability of the conjugate base.

    • Material Properties – Material properties of gases, fluids and solids – densities, specific heats, viscosities and more.

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