CH 208
Syllabus
References to Organic Chemistry by McMurry, 4th Ed., Brooks/Cole, 1996.
Chapter 14 Ultraviolet Spectroscopy
14.11 Structure Determination in Conjugated System: Ultraviolet Spectroscopy p. 519 14.12 Ultraviolet Spectrum of 1,3-Butadiene p. 520
14.13 Interpreting Ultraviolet Spectra: The Effect of Conjugation p. 522
14.14 Colored Organic Compounds p. 524
Summary and Key Words 527
Additional Problems 527
Chapter 12 Structure Determination: Mass
Spectrometry and Infrared Spectroscopy
12.1 Mass Spectrometry p. 425
12.2 Interpreting Mass Spectra p. 427
12.3 Interpreting Mass Spectral Fragmentation Patterns p. 429
12.4 Spectroscopy and the Electromagnetic Spectrum p. 433
12.5 Infrared Spectroscopy of Organic Molecules p. 437
12.6 Interpreting Infrared Spectra p. 439
12.7 Infrared Spectra of Hydrocarbons p. 443
12.8 Infrared Spectra of Other Functional Groups p. 444
Summary and Key Words 448
Additional Problems 448
Chapter 13: Nuclear Magnetic Resonance
Spectroscopy
13.1 Nuclear Magnetic Resonance Spectroscopy p. 455
13.2 The Nature of NMR Absorptions p. 457
13.3 Chemical Shifts p. 461
13.4 1H NMR Spectroscopy and Proton Equivalence p. 463
13.5 Chemical Shifts in 1H NMR Spectroscopy p. 464
13.6 Integration of 1H NMR Absorptions: Proton Counting p. 467
13.7 Spin-Spin Splitting in 1H NMR Spectra p. 468
13.8 More Complex Spin-Spin Splitting Patterns p. 473
13.9 Uses of 1H NMR Spectroscopy p. 476
13.10 13C NMR Spectroscopy: Signal Averaging and FT-NMR p. 477
13.11 Characteristics of 13C NMR Spectroscopy p. 479
13.12 DEPT 13C NMR Spectroscopy p. 482
13.13 Uses of 13C NMR Spectroscopy p. 484
Summary and Key Words p. 486
Additional Problems p. 487
Organic Reactions: A Brief Review p.p. 623-631
Chapter 17: ALCOHOLS AND THIOLS
17.2 Sources and Uses of Simple Alcohols p. 634
17.3 Properties of Alcohols: Hydrogen Bonding p. 635
17.4 Properties of Alcohols: Acidity and Basicity p. 637
17.5 Preparation of Alcohols 639
17.6 Alcohols from Reduction of Carbonyl Compounds p. 641
17.7 Alcohols from Addition of Grignard Reagents to Carbonyl Compounds p. 644
17.8 Reactions of Alcohols p. 648
17.9 Oxidation of Alcohols p. 653
17.10 Protection of Alcohols p. 656
17.11 Spectroscopic Analysis of Alcohols p. 659
17.12 Thiols p. 662
Summary and Key Wor p. ds p. 665
Summary of Reactions p. 666
Additional Problems p. 668
Chapter 18: ETHERS, EPOXIDES, AND
SULFIDES
18.2 Structure and Properties of Ethers p. 677
18.3 Industrial Preparation of Ethers p. 678
18.4 The Williamson Ether Synthesis p. 679
18.5 Alkoxymercuration/Demercuration of Alkenes p. 681
18.6 Reactions of Ethers: Acidic Cleavage p. 682
18.7 Cyclic Ethers: Epoxides p. 683
18.8 Ring Opening Reactions of Epoxi des p. 686
18.9 Crown Ethers p. 690
18.10 Spectroscopic Analysis of Ethers p. 691
18.11 Sulfides p. 693
Summary and Key Words p. 696
Summary of Reactions p. 697
Additional Problems p. 699
Chemistry of Carbonyl Compounds: An
Overview
I. Kinds of Carbonyl Compounds p. 706
II. Nature of the Carbonyl Group p. 707
III. General Reactions of carbonyl Compounds p. 709
Chapter 19: ALDEHYDES AND KETONES
19.1 Properties of Aldehydes and Ketones p. 717
19.2 Naming Aldehydes and Ketones p. 718
19.3 Preparation of Aldehydes p. 720
19.4 Preparation of Ketones p. 721
19.5 Oxidation of Aldehydes and Ketones p. 723
19.6 Nucleophilic Addition Reactions of Aldehydes and Ketones p. 724
19.7 Relative Reactivity of Aldehydes and Ketones p. 726
19.8 Nucleophilic Addition of H20: Hydration p. 727
19.9 Nucleophilic Addition of HCN: Cyanohydrins p. 730
19.10 Nucleophilic Addition of Grignard Reagents: Alcohol Formation p. 732
19.11 Nucleophilic Addition of Hydride: Reduction p. 732
19.12 Nucleophilic Addition of Amines: Imine and Enamine Formation p. 733
19.13 Nucleophilic Addition of Hydrazine: The Wolif-Kishner Reaction p. 737
19.14 Nucleophilic Addition of Alcohols: Acetal Formation p. 740
19.15 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction p. 743
19.16 The Cannizzaro Reaction p. 746
19.17 Conjugate Nucleophilic Addition to a,ß-Unsaturated Carbonyl Groups p. 748
19.18 Some Biological Nucleophilic Addition Reactions p. 752
19.19 Spectroscopic Analysis of Ketones and Aldehydes p. 753
Summary and Key Words p. 760
Summary of Reactions p. 761
Additional Problems p. 764
Chapter 20: Carboxylic Acids
20.1 Naming Carboxylic Acids p. 775
20.2 Structure and Physical Properties of Carboxylic Acids p. 777
20.3 Dissociation of Carboxylic Acids p. 778
20.4 Substituent Effects on Acidity p. 782
20 .5 Substituent Effects in Substituted Benzoic Acids p. 784
20.6 Preparation of Carboxylic Acids p. 786
20.7 Reactions of Carboxylic Acids p. 788
20.8 Reduction of Carboxylic Acids p. 789
20.9 Spectroscopic Analysis of Carboxylic Acids p. 790
Summary and Key Words p. 794
Summary of Reactions p. 794
Additional Problems p. 796
Chapter 21: Carboxylic Acid Derivatives
21.1 Naming Carboxylic Acid Derivatives p. 803
21.2 Nucleophilic Acyl Substitution Reactions p. 806
21.3 Relative Reactivity of Carboxylic Acid Derivatives p. 808
21.4 Nucleophilic Acyl Substitution Reactions of Carboxylic Acids p. 810
21.5 Chemistry ofAcid Halides p. 815
21.6 Chemistry of Acid Anhydrides p. 822
21.7 Chemistry ofEsters p. 824
21.8 Chemistry ofAmides p. 831.
21.9 Chemistry of Nitriles p. 833
21.10 Thiol Esters: Biological Carboxylic Acid Derivatives p. 838
21.11 Polyamides and Polyesters: Step-Growth Polymers p. 839
21.12 Spectroscopy of Carboxylic Acid Derivatives p. 843
Summary and Key Words p. 847
Summary of Reactions p. 848
Additional Problems p. 851
Chapter 24: ALIPHATIC AMINES
24.1 Naming Amines p. 935
24.2 Structure and Bonding in Amines p. 938
24.3 Physical Properties of Amines p. 940
24.4 Amine Basicity p. 941
24.5 Industrial Sources and Uses of Alkylamines p. 945
24.6 Synthesis of Amines p. 946
24.7 Reactions of Amines p. 954
24.8 Tetraalkylammornum Salts as Phase-Transfer Agents p. 956
24.9 Spectroscopy of Amines p. 957
Summary and Key Words p. 964
Summary of Reactions p. 964
Additional Problems p. 966
Chapter 25: Arylamines and Phenols
25.1 Basicity of Arylamines p. 974 4
25.2 Preparation of Arylamines p. 977
25.3 Reactionns of Arylamines p. 978
25.4 Phenols p. 985
25.5 Industrial Uses of Phenols p. 986
25.6 Properties of Phenols: Acidity p. 988
25.7 Preparation of Phenols p. 991
25.8 Reactions of Phenols p. 992
25.9 Spectroscopy of Arylamines and Phenols p. 997
Summary of Key Words p.1000
Summary of Reactions p. 1001
Additional Problems p.1004