CHEM&163 (S2016) Chapter 15 Acids and Bases Lecture Outline (M. Dunn)

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1 1. Acid Base theory by Three Definitions Lecture Slide 2. Acid/Base Theory: Arrhenius Acids and Bases Acid: Released H + in water (H3O + ) Base: Releases OH - in water My notes/reminders etc. Bronsted-Lowry Acid: Proton (H + ) Donor Base: Proton (H + ) Acceptor Lewis Acid: Electron pair Acceptor Base: Electron pair Acceptor Which definition is the most narrow? Which is the most broad? 3. Write a reaction for HNO3(aq) showing that it is an Arrhenius acid: What is the relationship between H + (aq) and H3O + (aq)? Why is H + often referred to as a proton? 4. Rank the following solutions from most acidic to most basic (water molecules have been omitted for clarity). Explain why: Page 1

2 5. Show the proton (H + ) transfer in this Bronsted-Lowry Acid/Base reaction H3O + + NH3 H2O + NH4 + Which compound is the acid? Why? Which compound is the base? Why? Could this example be used for an Arrhenius acid/base? Conjugate Acid/Base Pairs: Consider the backwards reaction Which compound is the acid? Why? Which compound is the base? Why? Label the CONJUGATE Acid and CONJUGATE Base Draw a line connecting the Acid to the Conjugate Base. What is the relationship between these two species? Draw a line connecting the Base to the Conjugate Acid. What is the relationship between these two species? 6. Show the proton (H + ) transfer in this Bronsted-Lowry Acid/Base reaction HNO3 + H2O H3O + + NO3 - Which compound is the acid? Why? Which compound is the base? Why? Label the CONJUGATE Acid and CONJUGATE Base How did you figure out the conjugates? Could this example be used to illustrate an Arrhenius acid/base reaction? Explain Page 2

3 7. Codeine, C18H21O3N is a Bronsted-Lowry (BL) base What is the conjugate acid of codeine? Write a net ionic equation to show codeine behaving as a BL base in water. Label the acid/base pairs Note Nitrogen containing compounds (neutral charge) often behave a BL bases. 8. Water is amphoteric. Define amphoteric: Note: For our purposes, amphoteric is the same thing as amphiprotic Referring to the reactions we ve already examined, Give an example of water acting as an ACID (BL) Give an example of water acting as a BASE (BL) 9. Lewis Acid Base theory: Reminder, in Lewis acid/base theory, the model is about accepting or donating. The acid is the. The base is the. In the following reaction, label the Lewis acid and Lewis base: The product contains a coordinate covalent bond. Define covalent bond? Label the coordinate covalent bond in the reaction. Could this reaction be used to illustrate Bronsted-Lowry Acid/Base theory? Why or Why not? Could this reaction be used to illustrate Arrhenius Acid/Base theory? Why or Why not? Page 3

4 10. Ammonia is a base by ALL three definitions. Write a reaction equation illustrating this according to each of the three acid/base theories. Arrhenius: Bronsted/Lowry: Lewis: 2. Strong Vs Weak Acids and Bases What do the symbols mean? 2. What are the differences between a strong acid and weak acid: a. Degree of ionization b. Composition of aqueous solution c. Conductor of electricity d. Anything else? 12. Write the generic BL reaction equation for a strong acid in water: 13. Write the generic BL reaction equation for a weak acid in water. 14. Strength of Acids and Bases Strong Acid Ionizes completely in aqueous solution Strong Base Ionizes completely in aqueous solution Solution composition: Weak Bases- Partially ionizes in aqueous solution NH 3 + H 2O NH H 3O + Solution composition: Page 4

5 15. The Strong Acids/Bases (These should be memorized!) If it doesn t appear on this list it is WEAK! Strong acids Strong Bases HClO 4 LiOH H 2SO 4 NaOH HNO 3 KOH HCl Ca(OH) 2 HBr Sr(OH) 2 HI Ba(OH) Relative Strengths of Acids and Bases 17. The stronger an acid, the weaker its conjugate base. The weaker an acid, the stronger its conjugate base. 18. Generic form of BL reaction equation for acid in water. Generic form for BL reaction equation for anion (base) in water. Write the BL reaction of formic acid with water. Write the BL reaction of Acetic acid in water. Write the BL reaction equation of formate ion in water. Write the reaction of acetate ion in water. Formic acid, HCHO 2, is a stronger acid than acetic acid, HC 2H 3O 2. Which is the stronger base: formate ion, CHO 2, or acetate ion, C 2H 3O 2? Page 5

6 Energy CHEM&163 (S2016) Chapter 15 Acids and Bases Lecture Outline (M. Dunn) POGIL: Relative Strength of Acids Why? Many molecules of interest behave as acids or bases. However, not all acids and bases have the same strength. Since the chemical behavior of acids and bases depends upon their strength, knowledge of relative acidity and basicity can be the key to predicting chemical reactivity. Learning Objective: Relate previous learned concepts to the relative strength of acids and bases, including electronegativity, resonance and bond energy, and energy profile diagrams. Information: The diagram in Model 1 shows the free energy change for the ionization of an acid. The energy difference between the products and reactants determines strength of an acid. The underlying principle is that the systems seek the lowest energy possible. If the products are lower in energy, the reaction will favor the products (equilibrium lies to the right). If the reactants are lower in energy, the reaction will favor the reactants (equilibrium lies to the left). All weak acids will have a positive value for ΔE rxn. MODEL 1: Reaction Profile showing the Energy Change for the ionization of a weak Acid E A ΔE rxn Reaction progress Page 6

7 Questions: 1. What is more stable, the acid HA or the ionized products (H + + A - )?? How do you know this? 2. The equilibrium constant for the dissociation of weak acids is known as Ka. Write the equilibrium expression (aka law of mass action) for the disassociation of the weak acid HA. 3. Is the Ka value larger than, smaller than, or equal to 1? 4. Draw a sketch similar to the energy profile show in in Model 1 for the weak acid, H-B, which is a stronger acid than H-A. Pay particular attention to the difference in energy between the reactants and products of the two reactions. 5. Which is stronger base, B - or A -? 6. Sketch a reaction profile similar to that in the model but for a strong acid that completely ionizes in water: H-X. Clearly show the energy difference between the reactant and products. Page 7

8 Structure Affects the Strength of an Acid 19. In determining the strength of the acid, the main issue is how easily the proton is removed Easily removed = Tightly held = There are THREE guidelines 20. Guideline #1 Strength of bond depends on size of atom How does bond strength correspond to acid strength? H-X; large X = strong acid Within a column (group), size is the main issue Compare acid strength HF HCl HBr HI 21. Guideline #2 The first one is easy (polyprotic acids) H 2SO 4 vs HSO 4 - H 3PO 4 vs H 2PO 4 vs HPO 4 2- Page 8

9 22. Guideline #3 The more polarized the bond is, the greater the acid strength Polarized bond Electron with drawing groups weaken the bond to H Think electronegativity When comparing two anions in the same row, electronegativity differences are more important than size differences. When comparing within a column size is more important. 23. Electron withdrawing groups weaken the bond (see guideline #3) COMPARE: H 3N, H 2O, HF 24. Sometimes you need to look down chain to find a difference in electron withdrawing power (See guideline #3) Which acid is strongest/weakest? Why? 25. Which acid is strongest/weakest? Why? 26. Not all H s within a structure are equally acidic. Draw a Lewis structure for sulfuric acid and acetic acid. Which H s are acidic? Why? Page 9

10 27. The issues summarized. 1. In a column/group SIZE matters (as X gets bigger, acid gets stronger) Only the size of the atom directly attached to the H matters. (Down chain doesn t matter) 2. In a row/period ELECTRON withdrawing matters (more electronegativity = stronger acid) If there is no difference in atoms directly attached to the H, look down chain 3. In a polyprotic acid, the first one is easy (more H s= stronger acid) 28. Concept Check: In each pair, consider the structures then predict which acid is the stronger one. Acids Key Issue Conclusion Justification 1. NH3 or PH3 2. HI or H2Te 3. H2SO3 or HSO3-4. H3AsO4 or H3PO4 5. HSO4 - or HSeO4 - INFORMATION: Resonance structures that increase stability are those that delocalize electrons over the molecule and place negative charge on electronegative atoms. For example, HNO 3 is a strong acid and HNO 2 is a weak acid because HNO 3 has more resonance structures that place the negative charge on difference oxygen atoms. Questions: 7. Draw the Lewis resonance structures of NO 3 - and NO 2 - and use them to explain why nitric acid is a strong acid and nitrous acid is a weak acid. Page 10

11 Application: 1. Explain why ethanol ( ) is considerably more acidic than ethane (CH 3CH 3). 2. Give one reason why acetic acid ( ) is a stronger acid than ethanol? 3. Predict which hydrogen in aspartic acid,, is the most acidic. Explain your reasoning. Determining the position of equilibrium based on Acid Strength The crabapple analogy Think of the crab apple as the proton Strength of acid refers to how quickly or aggressively those crab apples are thrown. This is a WAR of the acids Page 11

12 35. What we learn from the crab apple wars: How do we determine the equilibrium position? Remember what position of equilibrium means? Example: CH3COOH + NH3 CH3COO - + NH Identify the acids (one on each side) 2. Which acid is stronger: (See table) 3. Identify the stronger base (the stronger acid gives the weaker conjugate base) 4. Strongest acid and base react to give weaker acid and base 36. You try one: For the following reaction, equilibrium lies to the because is the stronger acid. C6H5OH + H2PO4 - H3PO4 + C6H5O - Acidic and Basic Properties of Pure Water Write the reaction for the autoionization of water. This means there are small amounts of ions present. So. What is the Keq expression? What does Kw mean? Meaning of ph poh SIG FIG RULE of Logs: # of digits in the mantissa = # of sig figs in the original number log(3.000x10 4 ) should be rounded to mantissa log(3x10 4 ) = , but this value should be rounded to 4.5 antilog(0.301) = , which should be rounded to 2.00, antilog(0.30) = , which should be rounded to 2.0 Page 12

13 Page 13

14 Proof of the relationship between ph and poh Acidic/basic ph poh Example solution [H + ] (M) [ OH-] (M) 0 1 M HCl 1 Gastric juices ph= Lemon Juice 3 Vinegar/Diet Coke 4 Tomato Juice 5 Coffee 6 Unpolluted rain 7 Pure water 8 Pancreatic fluid 9 Soap 10 Milk of Magnesia Household Ammonia Lye (1.0 M NaOH) Page 14

15 ph, poh [H + ] (M) ( this is sometimes given as [H 3O + ]) [H + ][OH - ]= 1X10-14 [OH - ] (M) poh=-log[oh - ] [OH - ]=10 -poh ph=-log[h + ] [H + ]=10 -ph ph ph=7 neutral ph>7 base p<7 acid ph+poh=14 poh [H + ] [OH - ] ph poh Acid/Base/or Neutral 1.0E-6 M 1.0E-8 M E-9M 3.3E-5 M Page 15

16 [H + ] [OH - ] ph poh Acid/Base/or Neutral 3.8E-6 M 9.4E-8 M E-9M 1.6E-5 M Answer key to be published on CANVAS. Page 16

17 Strategy Questions: Acid/Base ph calculations 1. You want to make up 3.00 L of aqueous hydrochloric acid, HCl(aq), that has a ph of How many grams of concentrated hydrochloric acid will you need? Concentrated hydrochloric acid contains 37.2 % HCl (wt/wt). This problem is an application of the following concepts: ph scale Degree of ionization of a strong acid Concentration terms, definitions and conversion between different terms (strict unit analysis). Dilution Page 17

18 What is the ph of a solution in which 15 ml of 0.1 M NaOH is added to 25 ml of 0.10 M HCl? Limiting reactant problem: RICE TABLE method There is a dilution factor Page 18

19 Page 19

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