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Organic Chemistry II

The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical (in silico) study. This is a textbook map of the chapter 11-24 of McMurry's "Organic Chemistry" textbook; it is not a copy of the original textbook, but is an original construction or remix of comparable OER content on LibreTexts to recreate its organization.

Organic Chemistry Chemistry

Author: Layne Morsch et al.
Publisher: LibreTexts
Source: LibreTexts
Language: EN
Category: Basic Sciences

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Contents· 156 sections

12: Structure Determination - Mass Spectrometry and Infrared Spectroscopy
12.00: Introduction
12.01: Mass Spectrometry of Small Molecules - Magnetic-Sector Instruments
12.02: Interpreting Mass Spectra
12.03: Mass Spectrometry of Some Common Functional Groups
12.04: Mass Spectrometry in Biological - Time-of-flight (TOF) Instruments
12.05: Spectroscopy and the Electromagnetic Spectrum
12.06: Infrared Spectroscopy
12.07: Interpreting Infrared Spectra
12.08: Infrared Spectra of Some Common Functional Groups
12.S: Structure Determination - Mass Spectrometry and Infrared Spectroscopy (Summary)
13: Structure Determination - Nuclear Magnetic Resonance Spectroscopy
13.00: Nuclear Magnetic Resonance Spectroscopy
13.01: The Nature of NMR Absorptions
13.02: The Chemical Shift
13.03: Chemical Shifts in H NMR Spectroscopy
13.04: Integration of H NMR Absorptions - Proton Counting
13.05: Spin-Spin Splitting in H NMR Spectra
13.06: H NMR Spectroscopy and Proton Equivalence
13.07: More Complex Spin-Spin Splitting Patterns
13.08: Uses of H NMR Spectroscopy
13.09: C NMR Spectroscopy - Signal Averaging and FT-NMR
13.10: Characteristics of C NMR Spectroscopy
13.11: DEPT C NMR Spectroscopy
13.12: Uses of C NMR Spectroscopy
13.S: Structure Determination - Nuclear Magnetic Resonance Spectroscopy (Summary)
14: Conjugated Compounds and Ultraviolet Spectroscopy
14.00: Introduction
14.01: Stability of Conjugated Dienes- Molecular Orbital Theory
14.02: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
14.03: Kinetic vs. Thermodynamic Control of Reactions
14.04: The Diels-Alder Cycloaddition Reaction
14.05: Characteristics of the Diels-Alder Reaction
14.06: Diene Polymers- Natural and Synthetic Rubbers
14.07: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy
14.08: Interpreting Ultraviolet Spectra- The Effect of Conjugation
14.09: Conjugation Color and the Chemistry of Vision
14.S: Conjugated Compounds and Ultraviolet Spectroscopy (Summary)
15: Benzene and Aromaticity
15.00: Introduction
15.01: Naming Aromatic Compounds
15.02: Structure and Stability of Benzene
15.03: Aromaticity and the Huckel 4n 2 Rule
15.04: Aromatic Ions
15.05: Aromatic Heterocycles - Pyridine and Pyrrole
15.06: Polycyclic Aromatic Compounds
15.07: Spectroscopy of Aromatic Compounds
15.S: Benzene and Aromaticity (Summary)
16: Chemistry of Benzene - Electrophilic Aromatic Substitution
16.00: Introduction
16.01: Electrophilic Aromatic Substitution Reactions - Bromination
16.02: Other Aromatic Substitutions
16.03: Alkylation and Acylation of Aromatic Rings - The Friedel-Crafts Reaction
16.04: Substituent Effects in Substituted Aromatic Rings
16.05: An Explanation of Substituent Effects
16.06: Trisubstituted Benzenes - Additivity of Effects
16.07: Nucleophilic Aromatic Substitution
16.08: Benzyne
16.09: Oxidation of Aromatic Compounds
16.10: Reduction of Aromatic Compounds
16.11: Synthesis of Polysubstituted Benzenes
16.S: Chemistry of Benzene - Electrophilic Aromatic Substitution (Summary)
17: Alcohols and Phenols
17.00: Introduction to Alcohols and Phenols
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 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)
18: Ethers and Epoxides Thiols and Sulfides
18.00: Introduction
18.01: Names and Properties of Ethers
18.02: Preparing 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: Interchapter - A Preview of Carbonyl Chemistry
18.S: Ethers and Epoxides Thiols and Sulfides (Summary)
19: Aldehydes and Ketones- Nucleophilic Addition Reactions
19.00: Chapter Objectives and Preview of Carbonyl Chemistry
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 Water- Hydration
19.06: Nucleophilic Addition of HCN- Cyanohydrin Formation
19.07: Nucleophilic Addition of Hydride and Grignard 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 -unsaturated Aldehydes and Ketones
19.14: Spectroscopy of Aldehydes and Ketones
19.S: Aldehydes and Ketones (Summary)
20: Carboxylic Acids and Nitriles
20.00: Chapter Objectives and Introduction to Carboxylic Acids
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)
21: Carboxylic Acid Derivatives- Nucleophilic Acyl Substitution Reactions
21.00: Chapter Objectives and Introduction to Carboxylic Acid Derivatives
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)
22: Carbonyl Alpha-Substitution Reactions
22.00: Chapter Objectives and Introduction to Carbonyl Alpha-Substitution Reactions
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)
23: Carbonyl Condensation Reactions
23.00: 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)