1 Brønsted-Lowry Acids and Bases 1 According to Brønsted and Lowry, an acid-base reaction is defined in terms of a proton transfer. By this definition, the reaction of Cl in water is: Cl(aq) + Cl (aq) (a q) Water is the base in this reaction. Acid and base reactions in General chemistry are always done in water. When a Brønsted-Lowry acid such as Cl is placed in water, a proton is transferred to a water molecule (water is the base); a conjugate acid is formed (the hydronium ion 3 + ) as well as a conjugate base (the chloride ion). In neutral pure water (no acid is present), the hydrogen ion concentration is about 1.0 x 10-7 M (p of 7). An increase in the concentration of hydrogen ions above 1.0 x 10-7 M gives an acidic solution, with a p less than 7. If the p is >7, it is considered a basic solution.
2 Strong Brønsted-Lowry Acids and Bases 2 Cl(aq) + Cl (aq) (a q) The criterion for acid strength is the extent of ionization in water. equilibrium = 2 chemical reactions in competition The mineral acids Cl, Br, I, 2 S 4, N 3, and Cl 4 are all strong acids. Strong bases are extensively ionized in water. Common strong bases include Na (soda lye), K (potash lye), Li, Cs, Mg() 2, Ca() 2, and Ba() 2. The relative strength of these acids and bases are defined by their reaction with water.
3 Weak Brønsted-Lowry Acids and Bases Weak acids are solutes that react reversibly with water to form 3 + ions, and there are two categories. molecules containing an ionizable hydrogen atom such as nitrous acid (N 2 ) cations such as the ammonium ion (N 4+ ). Weak bases are defined as solutes that react with water molecules to acquire a + ion and leave an hydroxide ion ( ) behind. An example of a weak base is the reaction of ammonia + water to give the ammonium cation and hydroxide anion. 3 Weak acids that will discussed in this book are acetic acid (C 3 C), boric acid ( 3 B 3 ), butanoic acid (C 3 C 2 C 2 C), formic acid (C), hydrocyanic acid (CN), and uric acid (C 5 3 N 4 3 ), and the fatty acid known as stearic acid [C 2 (C 2 ) 15 C 2 C, an 18-carbon acid]. Weak bases include ammonia (N 3 ), and amines such as methylamine (C 3 N 2 ), triethylamine [(C 3 ) 3 N], and pyridine (C 5 5 N. The relative strength of these acids and bases are defined by their reaction with water.
4 rganic Acids and Bases 4 Acid-Base chemistry is important in rganic chemistry. Many organic acids and bases are insoluble in water, so the classical Brønsted-Lowry definition does not formally apply. A very weak acid can react with a particularly strong base, and a very weak base may react with a particularly strong acid. A solvent other than water is required to put organic acids or bases into solution, and this other solvent is typically another organic compound. Diethyl ether (C 3 C 2 C 2 C 3 ), hexane (C 3 C 2 C 2 C 2 C 2 C 3 ), and dichloromethane (C 2 Cl 2 ) are common solvents. A water-organic solvent mixture is often required to make the acid-base components soluble.
5 Comparing an rganic Acid and Cl 5 Water reacts with the strong acid Cl or the much weaker organic acid formic acid (C). The reaction of formic acid and water generates the conjugate base known as the formate anion, and the conjugate acid, the hydronium ion. Formic acid is a weaker acid than Cl, so the equilibrium lies to the left for C when compared with the equilibrium for Cl. Note the (aq) term, which indicates solvation of that molecule or ion by the solvent, which is water. Note also that the term reaction is used for the acid-base equilibrium. Cl (aq) Cl 3 + (aq) (aq) C formic acid (aq) C (aq) (aq) formate anion
6 Comparing Two rganic Acids 6 Water might react as a base with the acid ethanol (C 3 C 2 ). If water is the base, ethanol, C or Cl can be the acid. In all cases, the oxygen of 2 removes a proton ( + ) from the acid, so all three acids are Brønsted-Lowry acids. Ethanol is known to be a much weaker than formic acid, so the equilibrium for this reaction lies almost entirely to the left. By comparing three different acids for ionization in water, an order of acid strength is established: Cl > C > ethanol. Cl (aq) Cl 3 + (aq) (aq) (aq) C C (aq) (aq) formic acid formate anion C 3 C 2 (aq) + 2 C 3 C 2 (aq) (aq) ethanol ethoxide
7 Acids in rganic Solvents Consider the reaction of formic acid using diethyl ether as a solvent rather than water. Note the (ether) term in the reaction, indicating solvation by ether rather than by water. The organic solvent diethyl ether is also the base, and the basic atom in diethyl ether is the oxygen. The reacts with the weak acid (formic acid) to give the formate anion (the conjugate base). The conjugate acid is the protonated form of ether (an oxonium ion. The equilibrium lies to the left in the reaction because that formic acid is a weak acid in ether, but the definition of strong or weak acid relating to dissociation in water no longer applies. The equilibrium for formic acid lies further to the left in ether than in water, so formic acid is a weaker acid in ether than in water. The strength of the acid depends on the base it reacts with, which is critical for establishing where the equilibrium lies, to the left or to the right. 7 C(ether) + C (ether) + (ether) formic acid diether ether formate anion an oxonium ion
8 8 Acids in Different rganic Solvents If Cl is placed in anhydrous (no water) methanol, where methanol is the solvent, the oxygen of the methanol is the only available base for reaction with the acid Cl. The term (ether) is used for solvation in the formic acid reaction to show the analogy to the water reaction, but the (methanol) designation is omitted in this case. Although it is understood that all components are solvated by the solvent methanol, the solvation term is usually omitted in rganic chemistry and it will be omitted throughout the book. The definition for ionization in water does not apply, but ionization is still the key to the acid base reaction regardless of solvent. An acid reacts with a base, regardless of solvent, but the extent of ionization changes with the solvent and with the base. The degree of ionization changes as the acid and the base are changed and also as the solvent is changed. C(ether) + C (ether) + (ether) formic acid diether ether formate anion an oxonium ion C 3 + Cl C 3 2 Cl methanol an oxonium ion
9 Equilibrium Constants 9 Cl (aq) Cl 3 + (aq) (aq) The equilibrium constant, K a (acidity constant) in given by the following generalized equation when the reaction is done in water. [ + ] [B ] K a = and for Cl in water K a = [B] [ 3 + ] [Cl ] [Cl] The equation needs a base: water K a = [conjugate acid] [acid] [base] [conjugate base] so, K a = [ 3 + ] [Cl ] [Cl] [base] The base in the Cl reaction is actually the water from the solvent. Where is the term for water in the first set of equations? In General chemistry the water is removed from the equation to simplify calculations. owever, when water is removed from the equilibrium constant equation this act also removes the base from the acid base equation.
10 Put the Base Back Into Acid-Base Reactions 10 The equilibrium constants for the formic acid reaction with ether as well as the methanol and Cl reaction must use the K a equations: [C ] [ ] K a = and K a = [C] [ ] [Cl ] [ C 3 2 ] [C 3 ] [ Cl ] Water is not used for many reactions found in rganic chemistry, and it is important to change the focus from acids that ionize in water to the concept that acids react with bases in order to ionize. It is important to remember that both the acid and the base must be identified in a reaction based on their reactivity.
11 There are Two Acid-Base Definitions. ow Are They Related? 11 A Brønsted-Lowry acid is defined as a proton donor and a Brønsted- Lowry base is a proton acceptor. A Lewis acid accepts an electron pair from a Lewis base, which donates an electron pair. When Cl reacts with water, the Brønsted-Lowry definition states that the proton (+) is donated to water, forming the hydronium ion. In this reaction, the oxygen atom of the water accepts the proton, but to accept the proton, the oxygen must donate two electrons to the and the accept two electrons from the oxygen - so the two definitions merge. The Lewis definition is more general because it focuses on transfer of electrons, and those atoms that are electron rich and electron donors, and those atoms that are electron deficient, and accept electrons. This definition is more important for tracking chemical reactions.
12 What appens When Water Accepts a Proton to Form the ydronium Ion? hydronium ion 12 The Lewis definition of a base is an electron donor and a Lewis base donates electrons to an atom other than hydrogen. The base donates two electrons to a proton. The definitions merge. A Brønsted-Lowry base accepts a proton by donating two electrons to that proton. A covalent bond requires two electrons. Therefore, bases may be defined as two electron donors to an electron deficient center. If the base donates electrons to a proton, it is a Brønsted-Lowry base. If the base donates electrons to an atom other than hydrogen, it is formally a Lewis base. A base is a two-electron donor.
13 Electron Flow and the Curved Arrow Formalism 13 hydronium ion All bases donate two electrons, and the electron flow is from the base to the acid, not from the acid to the base. An acid does not donate the proton, but rather the proton is attacked by the base to form a new bond to the proton, as shown for water and + to give the hydronium ion. A blue curved arrow is used to indicate the flow of electrons, and the electron flow is always from a source of high electron density to a point of low electron density. The direction of the arrow is always from the base to the proton of the acid, as illustrated.
14 No Free Protons 14 The reaction with water showed + as a free proton, but there is no such thing as a free proton; i.e., + by itself. The proton in common acids such as Cl or C have the hydrogen atom attached to another atom by a covalent bond. Electronegativity differences make the hydrogen atom in Cl polarized such that is electron deficient and positive (a protonlike atom), whereas the Cl is electron rich and negative. Therefore, a base does not react with a free proton but rather with an electron deficient hydrogen atom that is attached to another atom, as in Cl. When the base donates two electrons to the hydrogen atom, it literally pulls the proton away.
15 Cl Water and Cl Cl 15 The oxygen atom of water donates two electrons (it is the base) to the of Cl, and the -Cl bond breaks as the two electrons are used to form a new bond (-). The two electrons from the -Cl bond will migrate towards the chlorine atom, forming chloride ion, which is formally the conjugate base. A curved arrow represents the electron flow from the basic oxygen to the electron deficient of Cl, and the entire acid-base process is written as a chemical reaction. The hydronium ion is the conjugate acid. As the bond is formed by using the two electrons from the oxygen, the -Cl bond breaks and the two electrons in that bond are transferred to chlorine, forming the chloride ion, which has a negative charge.
16 Strength of Acids and Bases 16 To probe acid or base strength in an equilibrium, the structure of the acid must be compared with the structure of its conjugate acid, and the structure of the base compared with that of its conjugate base. Determining the K a for two different acids that react with the same base will make it possible to identify the stronger acid. Determining the K a for two reactions in which a common acid reacts with two different bases will make it possible to identify the stronger base. Such comparisons reveal structural differences of the acid/conjugate acid and base/conjugate base pair for both reactions.
17 Why is I more acidic than F? 17 -F BASE -BASE F -I BASE -BASE I K a = K a = [-Base] [F ] [F] [BASE] [-Base] [I ] I[BASE] In the presence of a common but unspecified base, the K a for the I reaction is larger than the K a for the F reaction (I is a stronger acid than F). The reaction of F with the base, gives -BASE as the conjugate acid and fluoride ion as the conjugate base. The reaction with I gives -BASE, but the conjugate base is the iodide ion. Both sides of each equation must be examined. First, examine the left side of each reaction: the strength of the F bond and the I bond.
18 Why is I more acidic than F? 18 -F BASE -BASE F -I BASE -BASE I K a = K a = [-Base] [F ] [F] [BASE] [-Base] [I ] I[BASE] A weaker X- bond makes K a larger The bond dissociation energy of the -I bond is kj mol 1, so the I bond is weaker than the -F bond (569.7 kj mol 1 ). The covalent radius of I (135 pm) is much greater than that of F (71 pm), so the bond distance between and I will be longer than the bond distance between -F. The distance between the and F nuclei along that bond is less than the distance between the and I nuclei, due to the much larger radius of the iodine. This is the bonding distance, and generally, a longer bond is a weaker bond. If the -I bond is weaker, it should break more easily when attacked by the base, pushing the reaction to the right, towards the conjugate acid and base. If the equilibrium is pushed to the right, K a is larger, so a weaker bond is consistent with a more acidity compound.
19 Why is I more acidic than F? -F BASE -BASE F K a = -I BASE -BASE I K a = [-Base] [F ] [F] [BASE] [-Base] [I ] I[BASE] 19 These are equilibrium reactions, so determining the strength of I and F is not sufficient to answer the question. The conjugate bases, fluoride ion and iodide ion, must also be examined. If one conjugate base is more stable than the other, the more stable ion will be less reactive. The iodide ion is less reactive because it is larger and less able to donate electrons (it is a weaker base) when compared with the fluoride ion (iodide ion is more stable than the fluoride ion). The iodide ion is less reactive and therefore more stable. If iodide ion is less reactive, there is a higher concentration of iodide relative to fluoride, which means that the equilibrium in the I reaction is pushed more to the right, and the equilibrium for F is pushed further to the left. If there is a lower concentration of the conjugate base (iodide ion), K a is smaller. If there is a higher concentration of the conjugate base (iodide ion), K a is larger.
20 Why does a more stable conjugate base make K a larger? 20 Why is iodide ion more stable and less reactive? First, compare the size of the ions using the ionic radii rather than the covalent radii used above. The ionic radius of the iodide ion (I 1 ) is reported to be 215 pm and that of the fluoride ion (F 1 ) is 136 pm. It is clear that the iodide ion is significantly larger. The fluoride ion and the iodide ion have the same charge (an excess of two electrons and a total of eight electrons). The charge is dispersed over a much larger area in the larger iodide ion, making it more difficult to donate those electrons to the acid. It is less reactive. The larger size of the ion and dispersal of charge over a larger area makes the ion less reactive with the conjugate acid, so it is less basic. There will be a higher concentration of the conjugate base/conjugate acid and a lower concentration of the acid/base, so K a is larger (a stronger acid). If a conjugate base is more reactive (less stable) there will be a lower concentration of the conjugate base/conjugate acid and a higher concentration of the acid/base, so K a is smaller (a weaker acid). I is a stronger acid (K a is larger) because of the weaker I bond and because the larger size of the iodide ion disperses the charge and makes that conjugate base less reactive.
21 Why is I more acidic than F? -F BASE -BASE F K a = -I BASE -BASE I K a = [-Base] [F ] [F] [BASE] [-Base] [I ] I[BASE] 21 These are equilibrium reactions, so determining the strength of I and F is not sufficient to answer the question. The conjugate bases, fluoride ion and iodide ion, must also be examined. If one conjugate base is more stable than the other, the more stable ion will be less reactive. The iodide ion is less reactive because it is larger and less able to donate electrons (it is a weaker base) when compared with the fluoride ion (iodide ion is more stable than the fluoride ion). The iodide ion is less reactive and therefore more stable. If iodide ion is less reactive, there is a higher concentration of iodide relative to fluoride, which means that the equilibrium in the I reaction is pushed more to the right, and the equilibrium for F is pushed further to the left. If there is a lower concentration of the conjugate base (iodide ion), K a is smaller. If there is a higher concentration of the conjugate base (iodide ion), K a is larger.
22 Why does a more stable conjugate base make K a larger? 22 Why is iodide ion more stable and less reactive? First, compare the size of the ions using the ionic radii rather than the covalent radii used above. The ionic radius of the iodide ion (I 1 ) is reported to be 215 pm and that of the fluoride ion (F 1 ) is 136 pm. It is clear that the iodide ion is significantly larger. The fluoride ion and the iodide ion have the same charge (an excess of two electrons and a total of eight electrons). The charge is dispersed over a much larger area in the larger iodide ion, making it more difficult to donate those electrons to the acid. It is less reactive. The larger size of the ion and dispersal of charge over a larger area makes the ion less reactive with the conjugate acid, so it is less basic. There will be a higher concentration of the conjugate base/conjugate acid and a lower concentration of the acid/base, so K a is larger (a stronger acid). If a conjugate base is more reactive (less stable) there will be a lower concentration of the conjugate base/conjugate acid and a higher concentration of the acid/base, so K a is smaller (a weaker acid). I is a stronger acid (K a is larger) because of the weaker I bond and because the larger size of the iodide ion disperses the charge and makes that conjugate base less reactive.
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