Lewis dot structures
Dots are used to represent the electrons in the valence shell of atoms, and covalent
bonding is indicated by pairs of electrons placed between atoms. Multiple bonds are
represented with multiple pairs of electrons. Note that non-bonding lone pairs should be
included.
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Chemistry 261 W2015 Lecture Notes I
CH EM 2 6 1 – I nt roduc t ory Orga nic Che m ist ry I
Cla ss N ot e s
Instructor: Christopher Cairo
University of Alberta
Department of Chemistry
CAIRO – University of Alberta 1
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Chemistry 261 W2015 Lecture Notes I
Table of Contents
I . I nt roduc t ion a nd re vie w ....................................................................... 6
Organic Chemistry ....................................................................................................... 6
Atomic Structure - The Atomic Model .......................................................................... 7
Atomic Structure – Orbitals .......................................................................................... 7
Formal Charge ........................................................................................................... 11
Resonance ................................................................................................................ 13
Resonance Forms ..................................................................................................... 13
Formal Charges in Resonance Forms ....................................................................... 15
Some notes on Drawing Organic Structures: ............................................................. 11
Acids and Bases - Brønsted-Lowry (BL) Theory ........................................................ 16
Prediction of Direction of Acid-Base Reactions From pKa’s ....................................... 18
Acids and Bases in Aqueous Media .......................................................................... 19
Prediction of Acid Strength – Factors Influencing Acidity........................................... 21
Inductive effects ......................................................................................................... 22
Atom hybridization ..................................................................................................... 23
Acids and Bases - Lewis Definition ............................................................................ 23
I I . St ruc t ure a nd prope rt ie s of orga nic m ole c ule s ................................ 2 5
Chemical Bonding...................................................................................................... 25
Rules for forming Molecular Orbitals (MO) ................................................................ 29
Hybridization of Orbitals............................................................................................. 30
Structure of Ethane - CH3CH3 .................................................................................... 31
Structure of Ethylene (CH2=CH2) ............................................................................... 31
Structure of Acetylene (HCCH) ................................................................................ 33
Effect of Hybridization on Bond Lengths and Strengths............................................. 34
Hybridization of Nitrogen, Oxygen and Boron ............................................................ 34
VSEPR Model ............................................................................................................ 37
Physical Properties of Organic Molecules ................................................................. 37
Important Intermolecular Interactions ........................................................................ 37
Influence of Intermolecular Interactions on Physical Properties ................................ 39
Water solubility – trends. ........................................................................................... 41
Functional Groups ..................................................................................................... 42
Summary of Common Functional Groups .................................................................. 42
Alkyl Groups .............................................................................................................. 44
R groups .................................................................................................................... 44
Further Classification of Functional Groups Based on Degree of Substitution .......... 44
I I I . I nfra re d Spe c t rosc opy ...................................................................... 4 6
Absorption Spectroscopy ........................................................................................... 46
Infrared (IR) Spectroscopy ......................................................................................... 47
General IR Absorption Trends ................................................................................... 48
Spectral Regions ....................................................................................................... 48
Important Absorptions................................................................................................ 48
Effect of Structure on Carbonyl Stretching Absorption............................................... 49
Representative IR Spectra ......................................................................................... 52
CAIRO – University of Alberta 2
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Chemistry 261 W2015 Lecture Notes I
I V . St ruc t ure a nd st e re oc he m ist ry of a lk a ne s ...................................... 5 5
Alkanes ...................................................................................................................... 55
Classification of alkanes ............................................................................................ 55
Alkyl Groups .............................................................................................................. 57
Naming of Alkanes..................................................................................................... 58
Nomenclature of Alkyl Halides ................................................................................... 59
Nomenclature of Alcohols .......................................................................................... 60
Cycloalkanes ............................................................................................................. 60
Nomenclature of Cycloalkanes .................................................................................. 61
Cis/Trans Isomers...................................................................................................... 61
Nomenclature of Alkenes ........................................................................................... 62
Nomenclature of Alkynes ........................................................................................... 63
Properties of Alkanes................................................................................................. 64
Synthesis of Alkanes ................................................................................................. 66
Conformations of Ethane (CH3CH3) ........................................................................... 66
Conformations of Propane (CH3CH2CH3) .................................................................. 67
Conformations of Butane (CH3CH2CH2CH3) .............................................................. 69
Conformations and Stability of Cycloalkanes ............................................................. 71
Ring Strain ................................................................................................................. 71
Conformation of Cyclopropane .................................................................................. 71
Conformation of Cyclobutane .................................................................................... 72
Conformation of Cyclopentane .................................................................................. 72
Measuring conformational energy.............................................................................. 73
Conformation of Cyclohexane ................................................................................... 74
Conformations of Substituted Cyclohexanes ............................................................. 75
Bicyclic Compounds .................................................................................................. 78
V . T he st udy of c he m ic a l re a c t ions ....................................................... 8 0
General Types of Organic Reactions ......................................................................... 80
Why and How do reactions happen? ......................................................................... 80
Reaction Mechanisms ............................................................................................... 81
Types of Bond Cleavage and Bond Formation .......................................................... 81
Reaction Equilibria and Rates ................................................................................... 82
Reaction Thermodynamics ........................................................................................ 82
Reaction Kinetics ....................................................................................................... 84
Radical Generation .................................................................................................... 87
Reactions of Radicals – General Types..................................................................... 87
Radical Halogenation of Alkanes – Chain Reactions ................................................. 88
Reactive intermediates .............................................................................................. 92
V I . St e re oc he m ist ry ............................................................................... 9 3
Designation of Double Bond Stereochemistry ........................................................... 93
E/Z Nomenclature of Alkenes .................................................................................... 93
Enantiomers .............................................................................................................. 95
Examples of enantiomers. ......................................................................................... 96
Chirality ...................................................................................................................... 97
Specific Rotation ........................................................................................................ 98
R/S Nomenclature of Stereogenic Centers ................................................................ 99
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