Download Modules 261 12th edition

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Chem261
MODULE 1: The Basics: Bonding and Molecular Structure
Atomic Structure
- Isotopes
- Valence Electrons
Chemical Bonds: The Octet Rule
- Ionic bond
- Covalent bond
How to write Lewis Structures
Formal Charges and How to Calculate Them
Isomers: Different Compounds That Have the Same Molecular Formula
How to write and Interpret Structural Formula
- Dash Structural Formulas
- Condensed Structural Formulas
- Bond-Line Formulas
- How to Draw Bond-Line Formulas
- Three-Dimensional Formulas
Resonance Theory
- The Use of Curve Arrows
- How to Write Resonance Structures
- Rules For Writing Resonance Structures
- How To Decide When One Resonance Structure Contribute More To The Hybrid Than Another
Atomic Orbitals and Electron Configuration
Molecular Orbitals
The Structure of Methane and Ethane: sp3 Hybridization
The Structure of Ethene (Ethylene): sp2 Hybridization
- Restricted Rotation and the Double Bond
- Cis-Trans Isomerism
The Structure of Ethyne (Acetylene): sp Hybridization
How to Predict Molecular Geometry: The Valence Shell Electron Pair Repulsion Model
- Methane
- Ammonia
- Water
- Boron Trifluoride
- Beryllium Hydride
- Carbon Dioxide
Text Sections: 1.2-1.17
Homework:
Chapter 1:1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9, 1.10, 1.11, 1.12, 1.14, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20,
1. 21, 1.22, 1.23, 1.24, 1.25, 1.27, 1.28, 1.29, 1.30, 1.31, 1.32, 1.35, 1.36, 1.37, 1.38, 1.39, 1.40, 1.41, 1.43,
1.44, 1.45, 149, 1.50
MODULE 2: Families of Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared (IR)
Spectroscopy
Hydrocarbons: Representative Alkanes, Alkenes, Alkynes, and Aromatic Compounds
- alkanes
- alkenes
- alkynes
- benzene: A representative Aromatic hydrocarbon
Polar Covalent Bonds
Polar and Nonpolar Molecules
Dipole Moments in Alkenes
Functional Groups
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- alkyl groups and the symbol R
- phenyl and benzyl groups
- alkyl halides or haloalkanes
- alcohols and Phenols
- ethers
- amines
- aldehydes and ketones
- carboxylic acids
esters
amides
- nitriles
Summary of Important Families of Organic Compounds
Physical Properties and Molecular Structures
- Ionic Compounds: ion-ion forces
Intermolecular Forces (Van der Waals Forces)
- dipole –dipole forces
- hydrogen bonds
- Dispersion Forces
Dipole-Dipole Forces
Boiling Points
Solubilities
Guidelines for Water Solubility
Summary of Attractive Electronic Forces
Infrared Spectroscopy: An Instrumental Method for Detecting Functional Groups
Interpreting IR Spectra
Infrared Spectra of Hydrocarbons
IR Spectra of Some Functional Groups Containing Heteroatoms
How to Interpret an IR Spectrum without Any Knowledge of the Structure
Applications of Basic Principles
How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency
Text Sections: 2.1-2.17, 4.17
Homework:
Chapter 2: 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2. 9, 2.10, 2.12,2.15, 2.17, 2.18, 2.19, 2.20, 2.21, 2.22, 2.23, 2.24, 2.25,
2.26, 2.27, 2.29, 2.30, 2.31, 2.32, 2.33, 2.34, 2.35, 2.36, 2.37, 2.38, 2.39, 2.40, 2.43, 2.44, 2.45, 2.46, 2.47,
2.48, 2.50, 2.51, 2.52, 2.53, 2.54, 2.56
MODULE 3: An Introduction to Organic Reactions and Their Mechanism: Acids and Bases
Acid-Base Reactions
- the Bronsted-Lowry Definition of acids and Bases
- the Lewis Definition of Acids and Bases
- opposite charge attract
How to Use Curved Arrows in Illustrating Reactions
Lewis Acids and Bases
Heterolysis of Bonds to Carbon
- Carbocations
- Carbanions
- Electrophiles
- Nucleophiles
The Strength of Bronsted-Lowry Acids and Bases: Ka and pka
- The Acidity Constant, Ka
Acidity and pka
- Predicting the Strength of Bases
How to Predict the Outcome of Acid-Base Reactions
Relationship between Structure and Acidity
- The Effect of Hybridization
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- Inductive Effect
Acidity: Carboxylic Acids versus Alcohols
- The effect of Delocalization
- The Inductive Effect
- Summary and a Comparison of Conjugate Acid-Base Strength
- Inductive Effect of Other Groups
- Strength of Phenols and Acids
- Distinguishing and Separating Phenols from Alcohols and Carboxylic Acids
The Effect of Solvents on Acidity
Organic Compounds as Bases
A mechanism for an Organic Reaction
Acids and Bases in Non-aqueous Solution
Acid and Bases and the Synthesis of Deuterium and Tritium-Labeled Compounds
Text Sections: 3.1-3.7, 3.10-3.15.
Homework:
Chapter3: 3.1, 3.2, 3.3, 3.4, 3.6, 3.7, 3.8, 3.9, 3.13, 3.14, 3.16, 3.17, 3.18, 3.19, 3.20, 3.21, 3.22, 3.23, 3.24, 3.25, 3.26,
3.27, 3.29, 3.30, 3.32, 3.34, 3.35, 3.36, 3.38
MODULE4: Nomenclature and Conformations of Alkanes and Cycoalkanes
Introduction to alkanes and Cycloalkane
Shape of Alkanes
How to name Alkanes, Alkyl Halides, and Alcohols: The IUPAC System
- nomenclature of unbranched alkyl groups
- nomenclature of branched-chain alkanes
- nomenclature of branched alkyl groups
- classification of hydrogen atoms
- nomenclature of alkyl halides
- nomenclature of alcohols
How to Name Cycloalkanes
- monocyclic compounds
- bicyclic compounds
How to Name Alkenes and Cycloalkenes
How to Name Alkynes
Physical Properties of Alkanes and Cycloalkanes
Sigma Bonds and Bond Rotation
Newman Projections and How to Draw Them
How to do Conformational Analysis
Conformational Analysis of Butane
Stereoisomers and Conformational Stereoisomers
The relative Stabilities of Cycloalkanes: Ring Strain
-cyclopropane
-cycobutane
-cyclopentane
Conformations of Cyclohexane: The chair and the boat
Conformations of Higher Cycloalkanes
Substituted Cyclohexanes: Axial and Equatorial Hydrogen Groups
How to Draw Chair Conformational Structures
A Conformational Analysis of Methylcyclohexane
1,3-Diaxial interactions of a tert-Butyl Group
Disubstituted Cycloalkanes: Cis – trans Isomerism
Cis –Trans isomerism and Conformational Structures of Cyclohexanes
Bicyclic and Polycyclic Alkanes
Chemical Reactions of Alkanes
Synthesis of Alkanes and Cycloalkanes
Hydrogenation of alkenes and alkynes
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How to Gain Structural Information from Molecular Formulas and the Index of Hydrogen Deficiency
Text Sections: 4.1-4.17.
Homework:
Chapter 4: 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 4.10, 4.11, 4.12, 4.15, 4.16, 4.17, 4.18, 4.19, 4.20, 4.21, 4.23, 4.24,
4.26, 4.27, 4.28, 4.29, 4.31, 4.33, 4.34, 4.35, 4.36, 4.37, 4.39, 4.40, 4.41, 4.42, 4.43, 4.46
MODULE5: Stereochemistry: Chiral Molecules
Chirality and Stereochemistry
Isomerism: Constitutional Isomers and Stereoisomers
Enantiomers and Chiral Molecules
Molecules having one Chirality Center are Chiral
Tetrahedral versus Trigonal Stereogenic Center
How to test for Chirality: Planes of symmetry
Naming Enantiomers: The R, S –System
How to Assign (R) and (S) Configurations
Properties of Enantiomers: Optical Activity
- specific rotation
- Plane polarized light
- The polarimeter
Racemic forms
- Racemic forms and Enantiomeric Excess
The Synthesis of Chiral Molecules
- racemic Mixtures
Molecules with More than One Chirality Center
- How to Draw Stereoisomers for Molecules having more than one Chirality Center
- Meso compounds
- How to name Compounds with more than one Chirality Center
Fischer Projection Formulas
How to Draw and Use Fischer Projections
Stereoisomerism of Cyclic Compounds
- Cyclohexane Derivatives
Relating Configurations through Reactions in which No Bonds to the Stereogenic Carbon are broken
Relative and Absolute Configurations
Separation of Enantiomers: Resolution
Text Sections: 5.1- 5.4, 5.6-5.10, 5-12 –5-17.
Homework:
Chapter 5: 5.4, 5.5, 5.6, 5.8, 5.9, 5.10, 5.11, 5.12, 5.13, 5.14, 5.18, 5.19, 5.21, 5.22, 5.23, 5.24, 5.26, 5.27, 5.28, 5.33,
5.34, 5.35, 5.39, 5.40(a-i), 55.42, 5.43, 5.45, 5.46, 5.47
MODULE6. Nucleophilic Substitutions: Properties and Substitution Reactions of Alkyl Halides and
Alkyl Halides
Nucleophilic Substitution Reactions
Nucleophiles
Leaving Groups
Kinetics of a Nucleophilic Substitution Reaction: An SN2 Reaction
- How do we Measure the Rate of This Reaction?
- What is the Order of This Reaction?
A Mechanism for SN2 Reaction
The Stereochemistry of SN2 Reactions
The Reaction of Tert-Butyl Chloride with Water
A Mechanism for the SN1 Reaction
Carbocations
- The Structure of Carbocations
- The Relative Stabilities of Carbocations
The Stereochemistry of SN1 Reactions
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- Reactions that Involve Racemization
- Solvolysis
Factor Affecting the Rate of SN1 and SN2 Reactions
- The Effect of the Structure of the Substrate
- The Effect of the Concentration and Strength of the Nucleophile
- Solvent Effects in SN2 and SN1 Reactions
- The Nature of the Leaving Group
Organic Synthesis: Functional Group Transformations Using SN2 Reactions
Text Sections: 6.1- 6.6, 6.8-6-14.
Homework:
Chapter 6: 6.1, 6.2, 6.3, 6.5, 6.7, 6.8, 6.9, 6.10, 6.12, 6.13,6.14, 6.15, 6.16, 6.18, 6.20, 6.21, 6.22, 6.27, 6.29, 6.30, 6.35,
6.40, 6.41
MODULE7. Alkenes and Alkynes: Properties and Synthesis. Elimination Reactions of Alkyl Halides
Introduction
PHYSICAL Properties of Alkenes and Alkynes
The (E) – (Z) System for Designating Alkene Diastereomers
How to Use the (E) –(Z) System
Relative Stabilities of Alkenes
- heat of reaction
- overall relative stabilities of alkenes
Cycloalkenes
Synthesis of Alkenes: Elimination Reactions
Dehydrohalogenation of Alkyl Halides
- Bases Used in Dehydrohalogenation
- Mechanism of Dehydrohalogenation
The E2 Reaction
- Zaitsev’s Rule: Formation of the more Substituted Alkene is Favored with a Small Bases
- Formation of the Less Substituted Alkenes Using a Bulky Base
- The Stereochemistry of E2 Reactions: The Orientation of Group in the Transition State
How to Favor an E2 Mechanism
Elimination and Substitution Reactions Compete with Each Other
How to Determine Substitution or Elimination is Favored
Elimination of Alcohols: Acid-Catalyzed Dehydration
- Mechanism for Dehydration of Secondary and Tertiary Alcohols: An E1 Reaction
- Carbocation Stability and Transition State
Carbocation Stability and Occurrence of Molecular Rearrangements
- Rearrangements During Dehydration of Secondary Alcohols
- Rearrangement After Dehydration of a Primary Alcohol
The Acidity of Terminal Alkynes
Synthesis of Alkynes by Elimination Reactions
Practical Considerations for Alkyne Synthesis by Double Dehyrohalogenation
The Terminal Alkynes Can be converted to Nucleophiles for Carbon-Carbon Bond Formation
General Principle of Structure and Reactivity Illustrated by the Alkylation of Alkynide Anion
Text Sections: 7.1- 7-7, 7.9-7.10(a-b), 7.11-7.14
Homework:
Chapter 7: 7.1, 7.2, 7.3, 7.4, 7.6, 7.7, 7.8, 7.10, 7. 11, 7.12, 7.13, 7.14, 7.15, 7.16, 7.17, 7.19, 7.22, 7.27, 7.28, 7.29, 7.30,
7.33, 7.34, 7.35, 7.36, 7.37, 7.38, 7.39, 7.43, 7.44, 7.44, 7.46, 7.47, 7.49, 7.50, 7.52, 7.53
T.W.GrahamSolomons , Craig B. Fryhle and Scott A. Snyder Organic Chemistry, 12th edition
The End