Organic Chemistry 6 th Edition Paula Yurkanis Bruice. Chapter 1. Electronic Structure and Bonding. Acids and Bases Pearson Education, Inc.
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1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 1 Electronic Structure and Bonding Acids and Bases 2011 Pearson Education, Inc. 1
2 Organic Chemistry Carbon-containing compounds were once considered organ compounds available only from living organisms. The synthesis of the simple organic compound urea in 1828 showed that organic compounds can be prepared in the laboratory from non-living material. Today, organic natural products are routinely synthesized in the laboratory Pearson Education, Inc. 2
3 Why Carbon? Carbon neither gives up nor accepts electrons because it is in the center of the second periodic row. Consequently, carbon forms bonds with other carbons and other atoms by sharing electrons. The capacity of carbon to form bonds in this fashion makes it the building block of all living organisms Pearson Education, Inc. 3
4 Why Study Organic Chemistry? Since carbon is the building block of all living organisms, a knowledge of Organic Chemistry is a prerequisite to understanding Biochemistry, Medicinal Chemistry, and Pharmacology. Indeed, Organic Chemistry is a required course for studying Pharmacy, Medicine, and Dentistry. Admission into these professional programs is highly dependent on your performance in Organic Chemistry Pearson Education, Inc. 4
5 Examples of Organic Compounds Used as Drugs Methotrexate, Anticancer Drug 5-Fluorouracil, Colon Cancer Drug AZT, HIV Drug 2011 Pearson Education, Inc. Tamiflu, Influenza Drug 5
6 Examples of Organic Compounds Used as Drugs Haldol, Antipsychotic Elavil, Antidepressant Prozac, Antidepressant 2011 Pearson Education, Inc. Viagra, Treats Erectile Dysfunction 6
7 The Structure of an Atom An atom consists of electrons, positively charged protons, and neutral neutrons. Electrons form chemical bonds. Atomic number: numbers of protons in its nucleus Mass number: the sum of the protons and neutrons of an atom Isotopes have the same atomic number but different mass numbers. The atomic weight: the average weighted mass of its atoms Molecular weight: the sum of the atomic weights of all the atoms in the molecule 2011 Pearson Education, Inc. 7
8 The Distribution of Electrons in an Atom Quantum mechanics uses the mathematical equation of wave motions to characterize the motion of an electron around a nucleus. Wave functions or orbitals tell us the energy of the electron and the volume of space around the nucleus where an electron is most likely to be found. The atomic orbital closer to the nucleus has the lowest energy. Degenerate orbitals have the same energy Pearson Education, Inc. 8
9 2011 Pearson Education, Inc. 9
10 The ground-state electronic configuration describes the orbitals occupied by the atom s electrons with the lowest energy 2011 Pearson Education, Inc. 10
11 The following principles determine which orbitals electrons occupy: The Aufbau principle: an electron always goes to the available orbital with the lowest energy The Pauli exclusion principle: only two electrons can occupy one atomic orbital and the two electrons have opposite spin Hund s rule: electrons will occupy empty degenerated orbitals before pairing up in the same orbital 2011 Pearson Education, Inc. 11
12 Lewis s theory: an atom will give up, accept, or share electrons in order to achieve a filled outer shell or an outer shell that contains eight electrons 2011 Pearson Education, Inc. 12
13 Ionic Bonds Are Formed by the Transfer of Electrons Attractive forces between opposite charges are called electrostatic attractions 2011 Pearson Education, Inc. 13
14 Covalent Bonds Are Formed by Sharing Electrons 2011 Pearson Education, Inc. 14
15 2011 Pearson Education, Inc. 15
16 Equal sharing of electrons: nonpolar covalent bond (e.g., H 2 ) Sharing of electrons between atoms of different electronegativities: polar covalent bond (e.g., HF) 2011 Pearson Education, Inc. 16
17 A polar covalent bond has a slight positive charge on one end and a slight negative charge on the other 2011 Pearson Education, Inc. 17
18 2011 Pearson Education, Inc. 18
19 A Polar Bond Has a Dipole Moment A polar bond has a negative end and a positive end dipole moment (D) = µ = e x d (e) : magnitude of the charge on the atom (d) : distance between the two charges 2011 Pearson Education, Inc. 19
20 Electrostatic Potential Maps 2011 Pearson Education, Inc. 20
21 Lewis Structure Formal charge = number of valence electrons (number of lone pair electrons +1/2 number of bonding electrons) 2011 Pearson Education, Inc. 21
22 Nitrogen has five valence electrons Carbon has four valence electrons Hydrogen has one valence electron and halogen has seven 2011 Pearson Education, Inc. 22
23 Neutral Important Bond Numbers Cationic Anionic 2011 Pearson Education, Inc. 23
24 Non-Octet Species In the 3rd and 4th rows, expansion beyond the octet to 10 and 12 electrons is possible. Sulfuric Acid Periodic Acid Phosphoric Acid Reactive species without an octet such as radicals, carbocations, carbenes, and electropositive atoms (boron, beryllium). Nitric Oxide Radical, Mammalian Signaling Agent Radical Carbocation Carbene Borane 2011 Pearson Education, Inc. 24
25 2011 Pearson Education, Inc. 25
26 n orbital tells us the volume of space around the nucleus here an electron is most likely to be found The s Orbitals 2011 Pearson Education, Inc. 26
27 The p Orbitals 2011 Pearson Education, Inc. 27
28 Molecular Orbitals Molecular orbitals belong to the whole molecule. σ bond: formed by overlapping of two s orbitals. Bond strength/bond dissociation: energy required to break a bond or energy released to form a bond Pearson Education, Inc. 28
29 2011 Pearson Education, Inc. 29
30 In-phase overlap forms a bonding MO; out-of-phase overlap forms an antibonding MO: 2011 Pearson Education, Inc. 30
31 Sigma bond (σ) is formed by end-on overlap of two p orbitals: A σ bond is stronger than a π bond 2011 Pearson Education, Inc. 31
32 Pi bond (π) is formed by sideways overlap of two parallel p orbitals: 2011 Pearson Education, Inc. 32
33 Bonding in Methane 2011 Pearson Education, Inc. 33
34 Hybridization of One s and Three p Orbitals 2011 Pearson Education, Inc. 34
35 The orbitals used in bond formation determine the bond angles Tetrahedral bond angle: Electron pairs spread themselves into space as far from each other as possible 2011 Pearson Education, Inc. 35
36 The Bonds in Ethane 2011 Pearson Education, Inc. 36
37 Hybrid Orbitals of Ethane 2011 Pearson Education, Inc. 37
38 Bonding in Ethene: A Double Bond 2011 Pearson Education, Inc. 38
39 Bonding in Ethyne: A Triple Bond 2011 Pearson Education, Inc. 39
40 Bonding in the Methyl Cation 2011 Pearson Education, Inc. 40
41 Bonding in the Methyl Radical 2011 Pearson Education, Inc. 41
42 Bonding in the Methyl Anion 2011 Pearson Education, Inc. 42
43 Bonding in Water 2011 Pearson Education, Inc. 43
44 Bonding in Ammonia and in the Ammonium Ion 2011 Pearson Education, Inc. 44
45 Bonding in Hydrogen Halides 2011 Pearson Education, Inc. 45
46 Summary The shorter the bond, the stronger it is The greater the electron density in the region of orbital overlap, the stronger is the bond The more s character, the shorter and stronger is the bond The more s character, the larger is the bond angle 2011 Pearson Education, Inc. 46
47 Molecular Dipole Moment The vector sum of the magnitude and the direction of the individual bond dipole determines the overall dipole moment of a molecule 2011 Pearson Education, Inc. 47
48 Brønsted Lowry Acids and Bases Acid donates a proton Base accepts a proton Strong reacts to give weak The weaker the base, the stronger is its conjugate acid Stable bases are weak bases 2011 Pearson Education, Inc. 48
49 An Acid/Base Equilibrium K a = [H 3O + ][ A ] [H 2 O][ AH ] LogK a = pk a K a : The acid dissociation constant. The stronger the acid, the larger its K a value and the smaller its pk a value Pearson Education, Inc. 49
50 The Most Common Organic Acids Are Carboxylic Acids 2011 Pearson Education, Inc. 50
51 2011 Pearson Education, Inc. 51
52 Protonated alcohols and protonated carboxylic acids are very strong acids 2011 Pearson Education, Inc. 52
53 An amine can behave as an acid or as a base 2011 Pearson Education, Inc. 53
54 2011 Pearson Education, Inc. 54
55 Strong Acids / Bases React to Form Weak Acids / Bases 2011 Pearson Education, Inc. 55
56 The Structure of an Acid Affects Its Acidity The weaker the base, the stronger is its conjugate acid Stable bases are weak bases The more stable the base, the stronger is its conjugate acid 2011 Pearson Education, Inc. 56
57 The stability of a base is affected by its size and its electronegativity 2011 Pearson Education, Inc. 57
58 2011 Pearson Education, Inc. 58
59 When atoms are very different in size, the stronger acid will have its proton attached to the largest atom size overrides electronegativity 2011 Pearson Education, Inc. 59
60 When atoms are similar in size, the stronger acid will have its proton attached to the more electronegative atom 2011 Pearson Education, Inc. 60
61 Substituents Affect the Strength of an Acid 2011 Pearson Education, Inc. 61
62 Inductive electron withdrawal increases the acidity of a conjugate acid 2011 Pearson Education, Inc. 62
63 Acetic acid is more acidic than ethanol The delocalized electrons in acetic acid are shared by more than two atoms, thereby stabilizing the conjugated base 2011 Pearson Education, Inc. 63
64 A Summary of the Factors That Determine Acid Strength 1. Size: As the atom attached to the hydrogen increases in size, the strength of the acid increases 2. Electronegativity 2011 Pearson Education, Inc. 64
65 3. Hybridization 4. Inductive effect 2011 Pearson Education, Inc. 65
66 5. Electron delocalization 2011 Pearson Education, Inc. 66
67 Lewis Acids and Bases Lewis acid: non-proton-donating acid; will accept two electrons Lewis base: electron pair donors 2011 Pearson Education, Inc. 67
68 Basicity and Drug Design: Methotrexate, Substituting Nitrogen for Oxygen 2011 Pearson Education, Inc. 68
69 Acidity and Cosmetics: Skin Peel Agents Skin Peels: Remove old skin with an acid to expose new young-looking skin. The stronger the acid, the deeper the peel. Examples of skin peel agents: Mild Peel Agents: Deep Peel Agent: 2011 Pearson Education, Inc. 69
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