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Physical Properties of Cycloalkanes
Physical Properties of Alkanes
Columbia University C3443: Turro
Introduction
Organic Chemistry With a Biological Emphasis
Chapter 1: Introduction to organic structure and bonding I
Chapter 14: Reactions with stabilized carbanion intermediates II
Section 14.4: Pyridoxal phosphate - an electron sink cofactor
Section 14.5: Thiamine diphosphate-dependent reactions
Section 14.6: The transition state geometry of reactions involving pi bonds
Section 14.3: Elimination by the E1 and E2 mechanisms
Section 14.2: Variations on the Michael reaction
Section 14.P: Problems for Chapter 14
Aromaticity
Acid-Base Catalysis
Nucleophilicity & Basicity
Bonding & Molecular Structure
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Section 2.4: Solubility, melting points and boiling points
Section 3.10: Prochirality
Section 6.1: A first look at reaction mechanisms
Section 7.7: The effects of solvent and enzyme microenvironment on acidity
Section 8.6: Epoxides as electrophiles in nucleophilic substitution reactions
Section 11.7: A look ahead: addition of carbon and hydride nucleophiles to carbonyls
Section 12.7: A look ahead: acyl substitution reactions with a carbon or hydride nucleophile
Section 15.10: The Diels-Alder reaction and other pericyclic reactions
Section 17.3: Enzymatic reactions with free radical intermediates
Section 17.2: Radical chain reactions
Section 17.1: Structure and reactivity of radical species
Section 6.5: How enzymes work
Section 6.4: Protein structure
Section 6.3: Enzymatic catalysis - the basic ideas
Section 6.2: Energy diagrams
Section 5.1: The origin of the NMR signal
Section 5.2: Chemical equivalence
Section 5.3: The NMR experiment
Section 5.4: The basis for differences in chemical shift
Section 5.5: Spin-spin coupling
Section 5.6: 13C-NMR spectroscopy
Section 5.7 : Determining unknown structures
Section 5.8: NMR of phosphorylated molecules
Section 1.1: Atomic orbitals and electron configuration
Section 1.2: Chemical Bonds
Section 1.3: Drawing organic structures
Section 1.4: Functional groups and organic nomenclature
Section 1.5: Valence bond theory: sp, sp2, and sp3 hybrid orbitals
Section 13.6: Synthetic parallel - carbon nucleophiles in the lab
Chapter 13: Reactions with stabilized carbanion intermediates I
Section 13.1: Tautomers
Section 13.2: Isomerization reactions
Section 13.3: Aldol reactions
Section 13.4: Claisen reactions
Section 13.5: Carboxylation and decarboxylation reactions
Section 3.1: Conformations of straight-chain organic molecules, Newman projections
Section 2.3: Non-covalent interactions
Section 2.2: Resonance
Section 2.1: Molecular orbital theory: conjugation and aromaticity
Section 4.1: Introduction to molecular spectroscopy
Section 7.1: The ‘basic’ idea of an acid-base reaction
Section 2.P: Problems for Chapter 2
Section 7.2: The acidity constant
Section 7.3: Structural effects on acidity and basicity
Section 7.4: More on resonance effects on acidity and basicity
Section 7.5: Carbon acids and enolate ions
Section 7.6: Polyprotic acids
Section 7.P: Problems for Chapter 7
Section 6.P: Problems for Chapter 6
Section 5.P: Problems for Chapter 5
Section 8.5: Leaving groups
Section 8.4: Electrophiles and carbocation stability
Section 8.3: More about nucleophiles
Section 8.2: Two mechanistic models for a nucleophilic substitution reaction
Section 8.1: Introduction to the nucleophilic substitution reaction
Section 10.2: Phosphorylation reactions - kinase enzymes
Diels-Alder Cycloaddition
Chapter 11: Nucleophilic carbonyl addition reactions
Section 10.1: Overview of phosphates and phosphoryl transfer reactions
Section 10.3: Hydrolysis of phosphates
Section 10.P: Problems for Chapter 10
Hydroxyl Group Substitution
Nomenclature
Alcohol Nomenclature
Electrophilic Substitution at Oxygen
Elimination Reactions of Alcohols
Section 4.3: Ultraviolet and visible spectroscopy
Section 4.2: Infrared spectroscopy
Section 15.3: Electrophilic isomeration and substitution
Section 15.7: Carbocation rearrangements
Section 15.2: Electrophilic addition
Section 15.4: Another kind of electrophilic addition-elimination - shikimate to chorismate
Section 15.6: Synthetic parallel - electrophilic aromatic substitution in the lab
Section 16.1: Oxidation and reduction of organic compounds - an overview
Chapter 16: Oxidation and reduction reactions
Section 16.2: The importance of redox reactions in metabolism
Section 16.3: Outside the box - methanogenesis
Section 16.4: Hydrogenation/dehydrogenation reactions of carbonyls, imines, and alcohols
Section 16.5: Hydrogenation of alkenes and dehydrogenation of alkanes
Section 17.P: Problems for Chapter 17
Chapter 3: Conformations and Stereochemistry
Section 4.4: Mass Spectrometry
Chapter 7: Organic compounds as acids and bases
Chapter 8: Nucleophilic substitution reactions, part I
Chapter 10: Phosphoryl transfer reactions
Section 12.3: Thioesters
Section 12.4: Esters
Section 12.5: Nucleophilic acyl substitution reactions involving peptide bonds
Section 12.6: Activated amide groups
Section 15.9: Outside the box - 1,3-elimination and rearrangement in squalene synthase
Section 15.1: An overview of the different types of electrophilic reactions
Section 15.8: Cation-pi interactions and the stabilization of carbocation intermediates
Section 15.P: Problems for Chapter 15
Section 16.6: Additional examples of enzymatic hydride transfer reactions
Section 16.7: NAD(P)H, FADH2 and metabolism - a second look
Section 16.8: Observing the progress of hydrogenation and dehydrogenation reactions by UV spectroscopy
Section 16.9: Hydrogenation/dehydrogenation reactions and renewable energy technology
Section 16.P: Problems for Chapter 16
Section 16.13: Redox reactions in the organic synthesis laboratory
Section 16.10: Oxygenase reactions- flavin-dependent monoxygenases
Section 16.12: Redox reactions involving thiols and disulfides
Section 16.11: Halogenation of organic compounds
Section 11.2: Stereochemistry of the nucleophilic addition reaction
Section 11.3: Hemiacetals, hemiketals, and hydrates
Section 11.4: Acetals and ketals
Section 11.5: N-glycosidic bonds
Section 11.6: Imine (Schiff base) formation
Section 11.P: Problems for Chapter 11
Section 11.1: Nucleophilic additions to aldehydes and ketones: the general picture
Section 12.2: Acyl phosphates as activated carboxylic acids
Section 12.1: Introduction to carboxylic acid derivatives and the nucleophilic acyl substitution reaction
Section 12.P: Problems for Chapter 12
Section 1.P: Problems for Chapter 1
Section 3.5: Interactions between chiral molecules and proteins Edit section
Section 3.2: Conformations of cyclic organic molecules
Section 3.3: Stereoisomerism – chirality, stereocenters, enantiomers
Section 3.4: Naming chiral centers: the R and S system
Section 3.6: Optical activity
Section 3.7: Diastereomers
Section 3.8: Fischer and Haworth projections
Section 3.9: Stereochemistry and organic reactivity
Section 3.P: Problems for Chapter 3
Representative acid constants
Some characteristic absorption frequencies in IR spectroscopy
Typical coupling constants in NMR
Typical values for 13C-NMR chemical shifts
Typical values for 1H-NMR chemical shifts
The 20 common amino acids
Structures of common coenzymes
Some common laboratory solvents, acids, and bases
Examples of common functional groups in organic chemistry
Section 4.P: Problems for Chapter 4
Section 13.P: Problems for Chapter 13
Chapter 2 Solutions
Chapter 1 Solutions
Chapter 6 Solutions
Chapter 5 Solutions
Chapter 4 Solutions
Chapter 3 Solutions
Chapter 7 Solutions
Chapter 9 Solutions
Chapter 16 Solutions
Chapter 15 Solutions
Chapter 14 Solutions
Chapter 13 Solutions
Chapter 12 Solutions
Section 14.1: Michael additions, β eliminations and reactions with electron sink cofactors
Chapter 11 Solutions
Chapter 10 Solutions
Chapter 17 Solutions
Chapter 8 Solutions
Solution Manual
Section 9.3: Protein prenyltransferase - a hybrid SN1/SN2 substitution
Section 9.4: Biochemical nucleophilic substitutions with epoxide electrophiles
Section 9.2: Digestion of carbohydrate by glycosidase - an SN1 reaction
Section 9.P: Problems for Chapter 9
Section 9.1: Methyl group transfers: examples of SN2 reactions
Chapter 9: Nucleophilic substitution reactions, part II
Aromaticity
Virtual Textbook of OChem
Alcohols
Stereoisomers
Thiols and Sulfides
Intermolecular Forces
Fall 2010 Lectures
UM Morris Chem 2304: Soderberg
Amines
Nomenclature
Nomenclature of Carboxylic Acids
Natural Products
Related Derivatives
Predicting the Geometry of Organometallic Complexes
Preparation of Carboxylic Acids
Salt Reactions
Substitution of the Hydroxyl Hydrogen
Substitution of the Hydroxyl Group
Reduction & Oxidation Reactions of Carboxylic Acids
Carboxylic Acids
Phenols
Acidity of Phenols
Ring Substitution of Phenols
Oxidation of Quinones
COT
Blood Clotting Cascades
Boiling Points
Hydrogen Bonding
Electrophilic Substitution at Oxygen
Nomenclature of Aldehydes and Ketones
Occurrence of Aldehydes and Ketones
Properties of Aldehydes and Ketones
Carbonyl Group Reactions
Irreversible Addition Reactions of Aldehydes and Ketones
Reversible Addition Reactions of Aldehydes and Ketones
Alkene Stereoisomers
Conformational Stereoisomers
Alpha-carbon Reactions
Reactions of Aldehydes and Ketones
Alkane Heats of Combustion
Halogenation of Alkanes
Addition of Strong Brønsted Acids
Stereoselectivity in Addition Reactions to Double Bonds
Addition of Lewis Acids (Electrophilic Reagents)
Addition Reactions involving other Cyclic Onium Intermediates
Hydrogenation of Alkenes
Rearrangement of Carbocations
Addition Reactions of Alkenes
Addition Reactions Initiated by Electrophilic Halogen
Brønsted Acid Additions
Hydroxylation
Epoxidation
Addition of Radicals to Alkenes
Free Radical Reactions of Alkanes
Allylic Substitution
Addition Reactions of Dienes
Alkenes
Oxidations
Dienes
Cycloalkane Stereoisomer
Ethane Conformers
Alkyl Halide Occurrence
Alkyl Halide Reactions
Substitution and Elimination Reactions of Alkyl Halides
Nucleophilicity and Solvent Effects
SN2 Substitution Reactions and Alkyl Moiety
SN1 Substitution Reactions
Molecularity and Kinetics
Planar Conguration and Bredt's Rule
E2 Elimination Reactions
Stereochemistry of the E2 Reaction
E1 Elimination Reactions
Reactions of Alkyl Halides with Reducing Metals
Reactions of Dihalides
Alkyl Halides
Addition Reactions of Alkynes
Full Table of Contents
Catalytic Hydrogenation
Addition by Electrophilic Reagents
Hydration of Alkynes and Tautomerism
Hydroboration Reactions and Oxidations
Nucleophilic Addition Reactions & Reduction
Acidity of Terminal Alkynes
Alkynes
Nomenclature and Structure of Amines
Natural Nitrogen Compounds
Properties of Amines 1
Amine Reactions
Preparation of Amines
Reaction of Amines with Nitrous Acid
Reactions of Aryl Diazonium Salts
Substitution and Elimination Reactions of Amines
Oxidation States of Nitrogen
Ethers
Phosphines
Butane Conformers
Benzene and Other Aromatic Compounds
Fused Benzene Ring Compounds
Aromatic Systems and Factors Required for Aromaticity
Aromatic Ions and Antiaromaticity
Spectroscopy
Infrared Spectroscopy
Answers to IR Spec. Problems
Chirality and Symmetry
Symmetry and Point Groups
Examples of Point Groups
Enantiomorphism
Practice Problems
Optical Activity
Configurational Nomenclature
Multiple Stereogenic Centers
Fischer Projections
Meso Compounds
Other Configuration Notations
Resolution of Racemates
Conformational Enantiomorphism
Conformations of Biphenyls
Stereoisomerism in Disubstituted Cyclohexanes
Mass Spectrometry
Electrophilic Aromatic Substitution
Substitution Reactions of Benzene Derivatives
Electrophilic Substitution of Disubstituted Benzene Rings
Reactions of Substituent Groups
Reactions of Fused Benzene Rings
Characteristics of Specific Substitution Reactions of Benzenes
Alkanes
Aldehydes & Ketones
Benzene
Reactions of Carboxylic Acids
Videos
Empty
Nucleophilic Reactions of Benzene Derivatives
Sulfur and Phosphorus Compounds
Enderle Videos
Additional Methods of Hydroxyl Substitution
Section 9.5: Nucleophilic substitution over conjugated pi systems - the SN' mechanism
Lost
Isoprenoid biosynthesis
Nucleoside biosynthesis
Nucleotide catabolism
Amino acid biosynthesis
The E-Z system for naming alkenes
Amides
The phenyl group
What does "aromatic" really mean?
Omitting numbers
Rings: cis/trans and axial/equatorial relationships
Primary, Secondary, Tertiary, Quaternary Terms
Balancing Organic Redox Reactions
Index of Hydrogen Deficiency (IHD)
Case Study: Olestra
Organometallic Chemistry
Associative Ligand Substitution
Open Coordination Site
Quirky Ligand Substitutions
Dissociative Ligand Substitution
Ligand substitution
The trans/cis Effects & Influences
σ Complexes
Odd-numbered π Systems
Metal Alkyls
What is Organometallic Chemistry?
Resources for Organometallic Chemistry
Simplifying the Organometallic Complex (Part 1)
Ligand Field Theory & Frontier Molecular Orbital Theory
Carbenes
Phosphines
Appendix: Review of laboratory synthesis reactions
Fundamentals
Introduction to Organometallic Chemistry
Structural Fundamentals
Periodic Trends of the Transition Metals
Simplifying the Organometallic Complex (Part 3)
E1 Reaction

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