Organic Chemistry Text Book (CHEM 3401 and 3402)
- Home
- Chapter 1: A Review of General ChemistryToggle Dropdown
- 1.1 Introduction to Organic Chemistry
- 1.2 Electrons, Bonds, and Lewis Structures
- 1.3 Identifying Formal Charges
- 1.4 Atomic Orbitals
- 1.5 Valence Bond Theory
- 1.6 Molecular Orbital Theory/Hybridization
- 1.7 VSEPR Theory: Predicting Geometry
- 1.8 Dipole Moments and Molecular Polarity
- 1.9 Intermolecular Forces and Physical Properties
- Problem Set
- Videos for chapter 1
- Chapter 2: Molecular RepresentationsToggle Dropdown
- Chapter 3: Acids and BasesToggle Dropdown
- Chapter 4: Alkanes and CycloalkanesToggle Dropdown
- Chapter 5: StereochemistryToggle Dropdown
- Chapter 6: Chemical Reactivity and MechanismsToggle Dropdown
- Chapter 7: Substitution ReactionsToggle Dropdown
- Chapter 8: Addition Reactions of AlkenesToggle Dropdown
- 8.1 Introduction of Addition Reactions
- 8.1 Nomenclature of Alkenes
- 8.2 Hydrohalogenation of Alkenes
- 8.3 Hydration, Hydroboration, and Oxymercuration of Alkenes
- 8.4 Hydrogenation of Alkenes
- 8.5 Halogenation of Alkenes
- 8.6 Dihydroxylation, Epoxidation, and Ozonolysis of Alkenes
- Problem Set
- Chapter 8 Videos
- Chapter 9: AlkynesToggle Dropdown
- Chapter 10: RadicalsToggle Dropdown
- Chapter 11: SynthesisToggle Dropdown
- Problem Sets Organic Chemistry I (CHEM 3401)
- Chapter 12: Alcohols and PhenolsToggle Dropdown
- 12.1 Alcohol Structure
- 12.2 Solubility
- 12.3 Boiling Point & Melting Point
- 12.4 Nomenclature
- 12.5 Alcohol Acidity
- 12.6 Reactions of Alcohols and Phenols
- 12.6.1 Substitution of the Hydroxyl Hydrogen
- 12.6.2 Nucleophilic Substitution of the Hydroxyl Group
- 12.6.3 Elimination Reactions of Alcohols
- 12.6.4 Oxidation Reactions of Alcohols
- 12.6.5 Reactions of Phenols
- 12.7 Practice Problems
- 12.7.1 Alcohol Nomenclature 1
- 12.7.2 Alcohol Nomenclature 2
- 12.7.3 Alcohol Nomenclature 3
- 12.7.4 Formation of Carbonyl Compounds
- 12.7.5 Functional Relationships of Alcohols
- 12.7.6 Reactions of Alcohols & Phenols
- 12.7.7 Alcohol Reactions
- Chapter 13: Ethers and EpoxidesToggle Dropdown
- Chapter 14: Infrared Spectroscopy and Mass SpectrometryToggle Dropdown
- 14.1 Introduction fo Molecular Spectroscopy
- 14.2 Infrared Spectroscopy
- 14.2.1 Introduction
- 14.2.2 Vibrational Spectroscopy
- 14.2.3 Group Frequencies
- 14.2.4 Table of Characteristic IR Frequencies
- 14.3 Mass Spectrometry
- 14.3.1 The Mass Spectrometer
- 14.3.2 Characteristics of Mass Spectra
- 14.3.3 Isotopes
- 14.3.4 Fragmentation Patterns
- 14.3.5 High Resolution Spectra
- 14.3.6 MS Practice Problems
- 14.3.6a Problem 1
- 14.3.6b Problem 2
- 14.3.6c Problem 3
- 14.3.6d Problem 4
- 14.3.6e Problem 5
- 14.3.6f Problem 6
- 14.3.6g Problem 7
- 14.3.6h Problem 8
- Chapter 15: Nuclear Magnetic Resonance Spectroscopy and UV-Visible SpectroscopyToggle Dropdown
- 15.1 Nuclear Magnetic Resonance Spectroscopy
- 15.1.1 Background
- 15.1.2 Proton NMR Spectroscopy
- 15.1.2a Introduction to Proton NMR Spectroscopy
- 15.1.2b Chemical Shift
- 15.1.2c Signal Strength
- 15.1.2d Hydroxyl Proton Exchange and the Influence of Hydrogen Bonding
- 15.1.2e Pi-Electron Functions
- 15.1.2f Solvent Effects
- 15.1.2g Spin-Spin Interactions
- 15.1.2h Examples
- 15.1.3 Carbon NMR Spectroscopy
- 15.1.4 NMR Practice Problems
- 15.1.4a Problem 1
- 15.1.4b Problem 2
- 15.1.4c Problem 3
- 15.1.4d Problem 4
- 15.1.4e Problem 5
- 15.1.4f Problem 6
- 15.1.4g Problem 7
- 15.1.4h Problem 8
- 15.1.4i Problem 9
- 15.1.4j Problem 10
- 15.1.5 Table of Proton NMR Shifts
- 15.1.6 Table of Carbon NMR Shifts
- 15.2 UV-Visible Spectroscopy
- 15.2.1 Background
- 15.2.2 The Electromagnetic Spectrum
- 15.2.3 UV-Visible Absorption Spectra
- 15.2.4 The Importance of Conjugation
- 15.3 Spectroscopy Practice Problems
- Chapter 16: Conjugated Pi Systems and Pericyclic ReactionsToggle Dropdown
- Chapter 17: Aromatic CompoundsToggle Dropdown
- 17.1 Aromaticity
- 17.1.1 Benzene
- 17.1.2 Fused Ring Compounds
- 17.1.3 Other Aromatic Compounds
- 17.1.4 Antiaromaticity
- 17.1.5 Practice Problems
- 17.1.5a Problem 1
- 17.1.5b Problem 2
- 17.2 Reactions of Substituent Groups
- 17.2.1 Oxidation of Alkyl Side-Chains
- 17.2.2 Bromination of Alkyl Side-Chains
- 17.2.3 Reduction of Nitro Groups
- Chapter 17 Videos
- Chapter 18: Aromatic Substitution ReactionsToggle Dropdown
- 18.1 Electrophilic Aromatic Substitution Reactions
- 18.2 Electrophilic Aromatic Substitution Mechanism
- 18.3 Electrophilic Aromatic Substitution Activation/Deactivation and Orientation
- 18.4 Electrophilic Substitution of Disubstituted Benzene Rings
- 18.5 Practice Problems
- 18.5.1 Problem 1
- 18.5.2 Problem 2
- 18.5.3 Problem 3
- 18.5.4 Problem 4
- 18.5.5 Problem 5
- 18.5.6 Problem 6
- 18.5.7 Problem 7
- Chapter 18 Videos
- Chapter 19: Aldehydes and KetonesToggle Dropdown
- 19.1 Nomenclature
- 19.2 Preparation of Aldehydes and Ketones
- 19.3 Properties of Aldehydes and Ketones
- 19.4 Reactions of Aldehydes and Ketones
- 19.4.1 Addition Reactions
- 19.4.1a Hydration
- 19.4.1b Acetal Formation
- 19.4.1c Imine Formation
- 19.4.1d Cyanohydrin Formation
- 19.4.1e Hydride Reduction
- 19.4.1f Addition of Organometallic Reagents
- 19.4.2 Reduction of Aldehydes and Ketones
- 19.4.2a Wolff-Kishner Reduction
- 19.4.2b Clemmensen Reduction
- 19.4.3 Oxidation of Aldehydes and Ketones
- 19.5 Practice Problems
- 19.5.1 Problem 1
- 19.5.2 Problem 2
- 19.5.3 Problem 3
- 19.5.4 Problem 4
- 19.5.5 Problem 5
- 19.5.6 Problem 6
- 19.5.7 Problem 7
- 19.5.8 Problem 8
- 19.5.9 Problem 9
- 19.5.10 Problem 10
- 19.5.11 Problem 11
- 19.5.12 Problem 12
- Chapter 20: Carboxylic Acids and Their Derivatives
- 20.1 Nomenclature
- 20.2 Physical Properties
- 20.3 Acidity
- 20.4 Preparation of Carboxylic Acids
- 20.5 Reactions of Carboxylic Acids
- 20.5.1 Salt Formation
- 20.5.2 Substitution of the Hydroxyl Hydrogen
- 20.5.3 Substitution of the Hydroxyl Group
- 20.5.4 Reduction
- 20.5.5 Oxidation
- 20.6 Practice Problems-Carboxylic Acids
- 20.6.1 Nomenclature Practice-1
- 20.6.2 Nomenclature Practice-2
- 20.6.3 Acidity
- 20.6.4 Reactions of Carboxylic Acids
- 20.7 Carboxylic Acid Derivatives
- 20.7.1 Related Derivatives
- 20.7.2 Nomenclature
- 20.7.3 Reactions
- 20.7.3a Acyl Substitution
- 20.7.3b Nitrile Hydrolysis
- 20.7.3c Reductions
- 20.7.3d Reactions with Organometallic Reagents
- 20.7.3e Dehydration of Amides
- 20.7.4 Practice Problems-Carboxylic Acid Derivatives
- 20.7.4a Nomenclature Practice-1
- 20.7.4b Nomenclature Practice-2
- 20.7.4c Carbonyl Compounds
- 20.8 Practice Problems
- 20.8.1 Problem 1
- 20.8.2 Problem 2
- 20.8.3 Problem 3
- 20.8.4 Problem 4
- 20.8.5 Problem 5
- 20.8.6 Problem 6
- Chapter 21: Alpha Carbon Chemistry: Enols and EnolatesToggle Dropdown
- 21.1 Reactions at the Alpha Carbon
- 21.2 Alpha Halogenation of Enols and Enolates
- 21.3 Aldol Reaction
- 21.4 Claisen Condensation
- 21.5 Alkylation at the Alpha Position
- 21.5.1 Enolate Alkylation
- 21.5.2 Dicarbonyl Alkylation
- 21.5.3 Decarboxylation Following Alkylation
- 21.5.4 Conjugate Reactions
- 21.5.4a Michael Reaction
- 21.5.4b Robinson Annulation
- 21.5.4c With Hydrides and Organometallics
- 21.6 Practice Problem
- 21.6.1 Problem 1
- Org Chem II - Problem Sets - Collection (CHEM 3402)
- Problem Set
20.7.3e Dehydration of Amides
Amides are very polar, thanks to the n-π conjugation of the nitrogen non-bonded electron pair with the carbonyl group. This delocalization substantially reduces the basicity of these compounds (pKa ca. –1) compared with amines (pKa ca. 11). When electrophiles bond to an amide, they do so at the oxygen atom in preference to the nitrogen. As shown below, the oxygen-bonded conjugate acid is stabilized by resonance charge delocalization; whereas, the nitrogen-bonded analog is not. One practical application of this behavior lies in the dehydration of 1º-amides to nitriles by treatment with thionyl chloride. This reaction is also illustrated in the following diagram. Other dehydrating agents such as P2O5 effect the same transformation.
