6.2 Electron Movements in Brønsted Acid Base Reactions. Copyright 2018 by Nelson Education Limited 1
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1 6.2 Electron Movements in Brønsted Acid Base Reactions Copyright 2018 by Nelson Education Limited 1
2 Recall: Brønsted Acid Base Reactions often simply termed acid base reactions Recall: H + does not actually exist as a discrete species. It associates with the strongest base in the system. Copyright 2018 by Nelson Education Limited 2
3 Representations of acid base reactions in different systems: Copyright 2018 by Nelson Education Limited 3
4 6.3 Free Energy and Acid Strength Copyright 2018 by Nelson Education Limited 4
5 Copyright 2018 by Nelson Education Limited 5
6 Copyright 2018 by Nelson Education Limited 6
7 6.4 Qualitative Estimates of Relative Acidities Copyright 2018 by Nelson Education Limited 7
8 6.4.1 Electronegativity Higher electronegativity provides increased ability to accommodate negative charge. Copyright 2018 by Nelson Education Limited 8
9 6.4.2 Atomic size Larger atomic size for anion spreads out electron density. This increases ability to accommodate negative charge. Copyright 2018 by Nelson Education Limited 9
10 6.4.3 Induction Induction: removal of electron density from an atom by a strongly electronegative atom nearby This increases the ability to accommodate negative charge. Copyright 2018 by Nelson Education Limited 10
11 Strength of induction depends on electronegativity of atoms involved number of electronegative atoms involved proximity to charge Copyright 2018 by Nelson Education Limited 11
12 Example: Copyright 2018 by Nelson Education Limited 12
13 6.4.4 Hybridization Atoms in organic molecules are generally in sp 3, sp 2, or sp hybridization states. Since s orbitals lower in energy than p, greater s character leads to greater stability. Copyright 2018 by Nelson Education Limited 13
14 6.4.5 Charge delocalization Recall: Charge delocalization can be illustrated by resonance structures. Copyright 2018 by Nelson Education Limited 14
15 Resonance in carboxylate ion: Copyright 2018 by Nelson Education Limited 15
16 A proton can be removed from a carbon atom if a very strong base is present, and the resulting anion is stabilized Copyright 2018 by Nelson Education Limited 16
17 6.5 Relative Acidities of Positively Charged Acids Copyright 2018 by Nelson Education Limited 17
18 6.5.1 Electronegativity Higher electronegativity destabilizes a positive charge. Copyright 2018 by Nelson Education Limited 18
19 6.5.2 Atomic size As for anions, greater size leads to greater charge delocalization. Copyright 2018 by Nelson Education Limited 19
20 6.5.3 Induction Nearby electronegative atoms increase the effective positive charge on an atom, resulting in destabilization. Copyright 2018 by Nelson Education Limited 20
21 Alkyl groups stabilize positive charges by donating electron density. Copyright 2018 by Nelson Education Limited 21
22 6.5.4 Charge delocalization As with negatively charges, delocalization can stabilize positive charges by spreading the charge over a larger volume. Copyright 2018 by Nelson Education Limited 22
23 Ester oxonium more stabilized than ketone oxonium. Copyright 2018 by Nelson Education Limited 23
24 6.6 Quantitative Acidity Measurements Copyright 2018 by Nelson Education Limited 24
25 Acidity for organic acids often expressed using pk a : pk a = log K a lower pk a indicates a stronger acid higher pk a indicates a weaker acid Copyright 2018 by Nelson Education Limited 25
26 Copyright 2018 by Nelson Education Limited 26
27 6.6.1 Using pk a to measure base strength The strength of a base can be quantified using the pk a of its conjugate acid. Copyright 2018 by Nelson Education Limited 27
28 Pay special attention to the different ionized forms of NH 3. Copyright 2018 by Nelson Education Limited 28
29 6.6.2 Finding pk a values in a table Look for the acid that most closely resembles the group in question. Note any structural elements that may affect pk a : Electron-withdrawing groups, resonance contributors, etc. Copyright 2018 by Nelson Education Limited 29
30 6.7 Predicting Acid Base Equilibria Copyright 2018 by Nelson Education Limited 30
31 6.7.1 Quantitative prediction of equilibria Behaviour of organic acids and bases when mixed often determines the order in which bonds are broken and formed. pk a values can be used to predict whether an acid base equilibrium will favour the reactants or the products. Copyright 2018 by Nelson Education Limited 31
32 6.7.2 Qualitative prediction of equilibria Relative strength of acids and bases can be used to make qualitative predictions about equilibria. Copyright 2018 by Nelson Education Limited 32
33 6.7.3 Protonation states at various phs The pk a of an acid can be used to predict the protonation state at a particular ph. Acids are primarily in protonated form when ph is less than pk a in deprotonated form when ph is greater than pk a Copyright 2018 by Nelson Education Limited 33
34 If ph is very close to pk a value, a mixture of protonated and deprotonated states is observed. Copyright 2018 by Nelson Education Limited 34
35 6.8 Lewis Acids in Organic Reactions Copyright 2018 by Nelson Education Limited 35
36 A Lewis acid is an electron pair acceptor. A Lewis base is an electron pair donor. Common Lewis acids: BF 3, BBr 3, AlCl 3, FeCl 3, ZnCl 2, TiCl 4, Hg(OAc) 2 Copyright 2018 by Nelson Education Limited 36
37 6.9 Patterns in Acids and Bases Copyright 2018 by Nelson Education Limited 37
38 Trends in the periodic table can be used to quickly estimate relative strengths of acids and bases: Charges on heteroatoms within the same row: more electronegative elements stabilize negative charges Charges on heteroatoms within the same column: larger atoms stabilize both positive and negative charges Proximity of electron-withdrawing or electron-donating groups: electronegative atoms (electron-withdrawing) stabilize adjacent negative charges alkyl groups (electron-donating) stabilize adjacent positive charges Copyright 2018 by Nelson Education Limited 38
39 Chapter summary Acid base reactions can be represented using curved arrows. Structural features can be used in ranking acidity and basicity. Structural features can be used to identify the most acidic proton and/or most basic site within a molecule. pk a values provide a measure of acidity and indirectly basicity (via conjugate acid). pk a values can be used to determine the direction of an acid base equilibrium. Copyright 2018 by Nelson Education Limited 39
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