2.7 Acids and Bases: The Brønsted-Lowry Definition. Acids and Bases: The Brønsted-Lowry Definition. Acids and Bases: The Brønsted-Lowry Definition

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1 2.7 Acids and Bases: The Brønsted-Lowry Definition Two frequently used definitions of acidity The Brønsted-Lowry definition Lewis definition Brønsted-Lowry acid A substance that donates a hydrogen ion (proton; H + ) to a base Brønsted-Lowry base A substance that accepts a hydrogen ion (proton; H + ) from an acid Acids and Bases: The Brønsted-Lowry Definition Conjugate acid The product that results from protonation of a Brønsted-Lowry base Conjugate base The anion that results from deprotonation of a Brønsted-Lowry acid In a general sense Acids and Bases: The Brønsted-Lowry Definition Water can act either as an acid or as a base

2 2.8 Acid and Base Strength Acids differ in their ability to donate H + The exact strength of a given acid, HA, in water solution is described using the equilibrium constant K eq for the acid-dissociation equilibrium HA + H O A + H O K eq = + - H3O A HA H O 2 Acid and Base Strength The concentration of water, [H 2 O], remains nearly constant at 55.5 M at 25 C Can rewrite equilibrium expression using new quantity called the acidity constant K a Acidity constant K a A measure of acid strength in water For any weak acid HA, the acidity constant is given by the expression K a HA + H O A + H O K = K H O = a eq H3O A HA Acid and Base Strength HA + H O A + H O Equilibria for stronger acids favor the products (to the right) and thus have larger acidity constants Equilibria for weaker acids favor the reactants (to the left) and thus have smaller acidity constants Acid strengths are normally expressed using pk a values pk a The negative common logarithm of the K a pk a = -log K a Stronger acids (larger K a ) have smaller pk a Weaker acids (smaller K a ) have larger pk a

3 Acid and Base Strength Acid and Base Strength Self ionization of water H 2 O + H 2 O OH - + H 3 O + K a (acid) (solvent) [H3O ][A ] [HA] [H 3 O + ][OH - ] = [1.0 x 10-7 ][1.0 x 10-7 ] = K w = ion product constant for water K w = 1.00 x [H 2 O] = 55.4 M at 25.0 C [H3O ][OH ] [H O] 2 K a pk a [ Kw] [H2O] [ ] Acid and Base Strength Strong acid (BrØnsted-Lowry) One that loses H + easily Conjugate base holds on to the H + weakly (weak base) Strong acid has weak conjugate base Weak acid (BrØnsted-Lowry) One that loses H + with difficulty Conjugate base holds on to the H + strongly (strong base) Weak acid has strong conjugate base

4 2.9 Predicting Acid-Base Reactions from pk a Values An acid will donate a proton to the conjugate base of a weaker acid The conjugate base of a weaker acid will remove the proton from a stronger acid Predicting Acid-Base Reactions from pk a Values Product of conjugate acid must be weaker and less reactive than the starting acid Product of conjugate base must be weaker and less reactive than the starting base Worked Example 2.4 Predicting Acid Strengths from pk a Values Water has pk a = 15.74, and acetylene has pk a = 25. Which is the stronger acid? Does hydroxide ion react with acetylene?

5 Worked Example 2.5 Calculating K a from pk a According to the data in Table 2.3, acetic acid has pk a = What is its K a? 2.10 Organic Acids and Organic Bases Most biological reactions involve organic acids and organic bases Organic acid Positively polarized hydrogen atom Two main kinds of organic acids 1. Contains a hydrogen atom bonded to an oxygen atom (O-H) 2. Contains a hydrogen atom bonded to a carbon atom next to a C=O double bond (O=C-C-H) Organic Acids and Organic Bases Conjugate base Anion stabilized by having its negative charge on a highly electronegative atom Anion stabilized by resonance Methanol Acetic Acid Acetone

6 Organic Acids and Organic Bases Conjugate bases from methanol, acetic acid, and acetone The electronegative oxygen atoms stabilize the negative charge in all three Organic Acids and Organic Bases Carboxylic acids Contain the CO 2 H grouping Occur abundantly in all living organisms Involved in almost all metabolic pathways At cellular ph of 7.3 carboxylic acids are usually dissociated and exist as their carboxylate anions, CO 2 - Organic Acids and Organic Bases Organic bases Characterized by the presence of an atom with a lone pair of electrons that can bond to H + Nitrogen-containing compounds are common organic bases and are involved in almost all metabolic pathways Oxygen-containing compounds can act both as acids and as bases

7 2.11 The Lewis definition is broader than the Brønsted-Lowry definition Lewis acid an electrophile A substance with a vacant low energy orbital that can accept an electron pair from a base All electrophiles are Lewis acids Lewis base a nucleophile A substance that donates an electron lone pair to an acid All nucleophiles are Lewis bases Lewis Acids and the Curved Arrow Formalism To accept an electron pair a Lewis acid must have either: A vacant, low-energy orbital A polar bond to hydrogen so that it can donate H + Various metal cations, such as Mg 2+, are Lewis acids because they accept a pair of electrons when they form a bond to a base Compounds of group 3A elements, such as BF 3 and AlCl 3 are Lewis acids Have unfilled valence orbitals and can accept electron pairs from Lewis bases Many transition metals, such as TiCl 4, FeCl 3, ZnCl 2, and SnCl 4 are Lewis acids

8 Curved arrow formalism Indicates the direction of electron flow from the base to the acid Always means that a pair of electrons moves from the atom at the tail of the arrow to the atom at the head of the arrow For the reaction of boron trifluoride, a Lewis acid, with dimethyl ether, a Lewis base. All movement of electrons from the Lewis base to the Lewis acid is indicated by a curved arrow Further examples of Lewis acids Lewis bases A compound with a pair of nonbonding electrons that it can use in bonding to a Lewis acid Definition of Lewis base similar to Brønsted-Lowry definition H 2 O acts as a Lewis base Has two nonbonding electrons on oxygen

9 Most oxygen- and nitrogen- containing organic compounds are Lewis bases They have lone pair electrons Some compounds can act as both acids and bases Some compounds have more than one atom with a lone pair of electrons Reaction normally occurs only once in such instances The more stable of the two possible protonation products is formed Occurs with carboxylic acids, esters, and amides Worked Example 2.6 Using Curves Arrows to Show Electron Flow Using curved arrows, show how acetaldehyde, CH 3 CHO, can act as a Lewis base.

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