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Athabasca University Chemistry 360 Organic Chemistry II

CHEM 360 deals with the chemistry of carbon compounds through a study of the characteristic reactions of the common functional groups. The chemistry of alcohols, ethers, aldehydes and ketones, carboxylic acids and their derivatives, carbohydrates, and amines are discussed. Particular emphasis is placed on the study of reaction mechanisms, in an attempt to show similarities between apparently unrelated reactions. The importance of stereochemistry is stressed throughout the course.

Chemistry

Author: Dietmar Kennepohl
Publisher: Athabasca University
Source: LibreTexts
License: CC BY-NC-SA
Language: EN
Category: Basic Sciences

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Contents· 160 sections

Chapter 17: Alcohols and Phenols
17.001 Introduction
17.01 Naming Alcohols and Phenols
17.02 Properties of Alcohols and Phenols
17.03 Preparation of Alcohols: A Review
17.04 Alcohols from Carbonyl Compounds: Reduction
17.05 Alcohols from Reaction of Carbonyl Compounds: Grignard Reagents
17.06 Reactions of Alcohols
17.07 Oxidation of Alcohols
17.08 Protection of Alcohols
17.09 Phenols and Their Uses
17.10 Reactions of Phenols
17.11 Spectroscopy of Alcohols and Phenols
17.S: Alcohols and Phenols (Summary)
Chapter 18: Ethers and Epoxides Thiols and Sulfides
18.001 Introduction
18.01 Names and Properties of Ethers
18.02 Synthesis of Ethers
18.03 Reactions of Ethers: Acidic Cleavage
18.04 Reactions of Ethers - Claisen Rearrangement
18.05 Cyclic Ethers: Epoxides
18.06 Reactions of Epoxides: Ring-opening
18.07 Crown Ethers
18.08 Thiols and Sulfides
18.09 Spectroscopy of Ethers
18.10 A Preview of Carbonyl Compounds
18.S: Ethers and Epoxides; Thiols and Sulfides (Summary)
Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions
19.000 Chapter Objectives
19.01 Naming Aldehydes and Ketones
19.02 Preparing Aldehydes and Ketones
19.03 Oxidation of Aldehydes and Ketones
19.04 Nucleophilic Addition Reactions of Aldehydes and Ketones
19.05 Nucleophilic Addition of H2O: Hydration
19.06 Nucleophilic Addition of HCN: Cyanohydrin Formation
19.07 Nucleophilic Addition of Grignard Reagents and Hydride Reagents: Alcohol Formation
19.08 Nucleophilic Addition of Amines: Imine and Enamine Formation
19.09 Nucleophilic Addition of Hydrazine: The Wolff-Kishner Reaction
19.10 Nucleophilic Addition of Alcohols: Acetal Formation
19.11 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
19.12 Biological Reductions
19.13 Conjugate Nucleophilic Addition to alpha, beta-unsaturated Aldehydes and Ketones
19.14 Spectroscopy of Aldehydes and Ketones
19.S: Aldehydes and Ketones (Summary)
Chapter 20: Carboxylic Acids and Nitriles
20: Carboxylic Acids and Nitriles
20.000 Chapter Objectives
20.001 Introduction
20.01 Naming Carboxylic Acids and Nitriles
20.02 Structure and Properties of Carboxylic Acids
20.03 Biological Acids and the Henderson-Hasselbalch Equation
20.04 Substituent Effects on Acidity
20.05 Preparing Carboxylic Acids
20.06 Reactions of Carboxylic Acids: An Overview
20.07 Chemistry of Nitriles
20.08 Spectroscopy of Carboxylic Acids and Nitriles
20.S: Carboxylic Acids and Nitriles (Summary)
Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
21.000 Chapter Objectives
21.001 Introduction
21.01 Naming Carboxylic Acid Derivatives
21.02 Nucleophilic Acyl Substitution Reactions
21.03 Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
21.04 Chemistry of Acid Halides
21.05 Chemistry of Acid Anhydrides
21.06 Chemistry of Esters
21.07 Chemistry of Amides
21.08 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
21.09 Polyamides and Polyesters: Step-Growth Polymers
21.10 Spectroscopy of Carboxylic Acid Derivatives
21.S: Carboxylic Acid Derivatives (Summary)
Chapter 22: Carbonyl Alpha-Substitution Reactions
22.000 Chapter Objectives
22.001 Introduction
22.01 Keto-Enol Tautomerism
22.02 Reactivity of Enols: The Mechanism of Alpha-Substitution Reactions
22.03 Alpha Halogenation of Aldehydes and Ketones
22.04 Alpha Bromination of Carboxylic Acids
22.05 Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
22.06 Reactivity of Enolate Ions
22.07 Alkylation of Enolate Ions
22.S: Carbonyl Alpha-Substitution Reactions (Summary)
Chapter 23: Carbonyl Condensation Reactions
23.000 Chapter Objectives
23.01 Carbonyl Condensations: The Aldol Reaction
23.02 Carbonyl Condensations versus Alpha Substitutions
23.03 Dehydration of Aldol Products: Synthesis of Enones
23.04 Using Aldol Reactions in Synthesis
23.05 Mixed Aldol Reactions
23.06 Intramolecular Aldol Reactions
23.07 The Claisen Condensation Reaction
23.08 Mixed Claisen Condensations
23.09 Intramolecular Claisen Condensations: The Dieckmann Cyclization
23.10 Conjugate Carbonyl Additions - The Michael Reaction
23.11 Carbonyl Condensations with Enamines - The Stork Reaction
23.12 The Robinson Annulation Reaction
23.13 Some Biological Carbonyl Condensation Reactions
23.S: Carbonyl Condensation Reactions (Summary)
Chapter 24: Amines and Heterocycles
24.00 Chapter Objectives
24.01 Naming Amines
24.02 Structure and Properties of Amines
24.03 Basicity of Amines
24.04 Basicity of Arylamines
24.05 Biological Amines and the Henderson-Hasselbalch Equation
24.06 Synthesis of Amines
24.07 Reactions of Amines
24.08 Reactions of Arylamines
24.09 Heterocyclic Amines
24.10 Spectroscopy of Amines
24.S: Amines and Heterocycles (Summary)
Chapter 25: Biomolecules: Carbohydrates
25.000 Chapter Objectives
25.01 Classification of Carbohydrates
25.001 Introduction
25.02 Depicting Carbohydrate Stereochemistry: Fischer Projections
25.03 D, L Sugars
25.04 Configurations of Aldoses
25.05 Cyclic Structures of Monosaccharides: Anomers
25.06 Reactions of Monosaccharides
25.07 The Eight Essential Monosaccharides
25.08 Disaccharides
25.09 Polysaccharides and Their Synthesis
25.10 Other Important Carbohydrates
25.11 Cell-Surface Carbohydrates and Influenza Viruses
25.S: Biomolecules- Carbohydrates (Summary)
Chapter 26: Biomolecules: Amino Acids Peptides and Proteins
26.000 Chapter Objectives
26.001 Introduction
26.01 Structures of Amino Acids
26.02 Amino Acids, the Henderson-Hasselbalch Equation, and Isoelectric Points
26.03 Synthesis of Amino Acids
26.04 Peptides and Proteins
26.05 Amino Acid Analysis of Peptides
26.06 Peptide Sequencing: The Edman Degradation
26.07 Peptide Synthesis
26.08 Automated Peptide Synthesis: The Merrifield Solid-Phase Technique
26.09 Protein Structure
26.10 Enzymes and Coenzymes
26.11 How do Enzymes Work? Citrate Synthase
Chapter 27: Biomolecules - Lipids
27.000 Chapter Objectives
27.001 Introduction
27.01 Waxes, Fats, and Oils
27.02 Soap
27.03 Phospholipids
27.04 Prostaglandins and Other Eicosanoids
27.05 Terpenoids
27.06 Steroids
27.07 Biosynthesis of Steroids
Chapter 28: Biomolecules - Nucleic Acids
28.00 Chapter Objectives
28.01 Nucleotides and Nucleic Acids
28.02 Base Pairing in DNA: The Watson-Crick Model
28.03 Replication of DNA
28.04 Transcription of DNA
28.05 Translation of RNA: Protein Biosynthesis
28.06 DNA Sequencing
28.07 DNA Synthesis
28.08 The Polymerase Chain Reaction