Chapter 01 Structure Determines Properties part 2
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1 Chapter 01 Structure Determines Properties part 2 CEM 341: Spring 2012 Prof. Greg Cook
2 Resonance Section 1.8
3 Resonance Some molecules may have more than one correct Lewis structure These are NT isomers. They are resonance forms. 12
4 General Rules for Resonance Structures Individual resonance forms D NT EXIST - they represent the extremes. The actual chemical species is a hybrid of all the resonance forms. Resonance forms differ only in the distribution of pi or non-bonding electrons. Atoms do not move. Individual resonance forms must obey normal valency rules. You cannot break the octet rule. The actual hybrid is more stable than the individual resonance forms and the individual structures do not have to be equal in energy. 13
5 Example N3 ow many resonance forms are there? N 14
6 Example Benzene 15
7 Not all Resonance Forms are Equal Formamide C N 16
8 Writing rganic Structures Section 1.9
9 Structure Representation Lewis Dot Structures - all electrons are represented by dots around the atoms Kekulé Structures - atoms are drawn and lines represent shared electrons (covalent bonds) 2-chloro-4-methylpentane C C C C C C Kekulé Structure Cl 18
10 Structure Representation Condensed Structure - No bonds are shown and side groups are attached to the carbon before it C 3 C(C 3 )C 2 CClC 3 Condensed Structure Condensed Kekulé Structures C C 2 C C 3 Condensed Kekulé Structure C 3 C 3 Cl 19
11 Structure Representation Skeletal Line Structure - Carbons and ydrogens are not shown. Each end of a line and intersection between lines represent a carbon atom. All other atoms are drawn. Cl Line Structure 20
12 Line Structure Examples = C 3 C 3 C C 2 C 3 Br = C 3 C 2 C 2 Br = C 3 C C 3 hydrocortisone beta carotene 21
13 The Shapes of Some Simple Molecules Section 1.10
14 Water
15 Methane C C
16 VSEPR Valence Shell Electron Pair Repulsion Model - The most stable arrangement of groups attached to a central atom is the one that has the maximum separation of electron pairs (bonded or nonbonded). 25
17 Borane Example Why does B3 have a planar structure? B B 26
18 Double and Triple Bonds Double and Triple bonds also bond through p orbitals (sideways) and have planar and linear structures, respectively. In VSEPR they are treated as a single unit. C C C C C C C C 27
19 Molecular Dipole Moments Section 1.11
20 Dipole Moment Molecular Dipole Moment is the sum of all the individual bond dipole moments of a substance. Molecules can have polar bonds but have no molecular dipole CCl4 C2Cl2 dipole moment µ = 0 D dipole moment µ = 1.62 D 29
21 Curved Arrows and Chemical Reactions Section 1.12
22 Arrows are not Arrows In chemistry we use different kinds of arrows to indicate different things Reaction Arrow A B Equilibrium Arrow A B Resonance Arrow A B 31
23 Curved Arrows Curved arrows are used to track the flow of electrons in chemical reactions Arrows begin where the electrons were originally and points to where they end up A B A + B A B A + B 32
24 Dissociation and Combination Curved arrows can be used in a variety of situations 3 C + C Br + Cl 33
25 Acids and Bases: The Arrhenius View Section 1.13
26 Arrhenius Definition Acid - a substance that ionizes in water to give protons A + A Base - a substance that ionizes in water to give hydroxide ions M M + 35
27 Acid Strength The degree to which they ionize Strong acids - ionize completely Weak acids - not ionized much A + A K a = [+ ] [A - ] [A] pk a = -log 10 K a acidity constant 36
28 Acids and Bases: The Brønsted-Lowry View Section 1.14
29 Brønsted-Lowry Definition Brønsted-Lowry acid - a substance that donates a proton ( + ) Brønsted-Lowry base - a substance that accepts a proton A A acid base conjugate acid conjugate base K a = 3 A A 38
30 Water and Amide Is water an acid or a base? N + 39
31 Let s Look at some pkas acid pk a conj base Cl -3.9 Cl F 3.1 F
32 Let s Look at some pkas acid pk a conj base N 36 N C 4 60 C 3 41
33 ow Structure Affects Acid Strength Section 1.16
34 Structure and Acidity Bond Strength Electronegativity (stability of conj. base) Electron delocalization of conj. base (resonance) 43
35 Structure and Acidity Electronegativity - the more electronegative the conjugate base, the more stable the anion 44
36 Electronegativity and Acidity Electronegativity X X I Br Cl pk a F
37 Electronegativity and Acidity Electronegativity X X I Br pk a F F F 0.5 Cl 2.8 F
38 Acidity of Alcohols Alcohol functional groups are similar to water and their acidities are close 3 C
39 Acidity of Alcohols Alcohol functional groups are similar to water and their acidities are close 3 C
40 Delocalization of Anion Spreading out charge is a stabilizing affect - resonance has a large affect on acidity 10 47
41 Resonance and Acidity
42 Acid-Base Equilibrium Section 1.17
43 Equilibrium pkas help us predict reactions The equilibrium lies on the side of the more stable species reaction will be favorable if the stronger acid is on the left and weaker on the right Acid + Base Conj. Acid + Conj. Base 50
44 Equilibrium Which side will this equilibrium lie on?
45 Lewis Acids and Lewis Bases Section 1.18
46 Lewis Definition Lewis Acid - a substance that accepts a pair of electrons (forms a covalent bond) Lewis Base - a substance that donates a pair of electrons (to form a bond) Lewis Acid Lewis Base 53
47 Lewis acids and bases Brønsted acids and bases, by definition, are a subset of Lewis acids and bases Lewis acids and bases can be either charged or neutral 54
48 Lewis acids and bases Lewis acid/base concepts include some substitution reactions 55
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