Modren Organic Synthesis in The Laboratory

Contents:

Abbreviations and Acronyms xv

1 Fundamental Techniques 3
1.1 Safety! 3
1.2 Useful Preparations 5
1.3 Chromatography 17
1.4 Crystallization 22
1.5 Residual Solvent Peaks in Nuclear Magnetic Resonance 24

2 Functional Group Manipulations 28
2.1 Alcohol Oxidation State 28
2.2 Ketone Oxidation State 39
2.3 Acid Oxidation State 44

3 Oxidation 55
3.1 Alcohol to Ketone Oxidation State 55
3.2 Alcohol to Acid Oxidation State 68
3.3 Olefin to Diol 70
3.4 Aldehyde to Acid Oxidation State 76
3.5 Heteroatom Oxidations 78

4 Reductions 81
4.1 Alcohols to Alkanes 81
4.2 Aldehydes, Amides, and Nitriles to Amines 83
4.3 Carboxylic Acids and Derivatives to Alcohols 85
4.4 Esters and Other Carboxylic Acid Derivatives to Aldehydes 88
4.5 Ketones or Aldehydes to Alcohols 91
4.6 Ketones to Alkanes or Alkenes 98
4.7 Reductive Dehalogenations 104
4.8 Carbon–Carbon Double and Triple Bond Reductions 105
4.9 Heteroatom–Heteroatom Reductions 108

5 Carbon−Carbon Bond Formation 111
5.1 Carbon−Carbon Forming Reactions (Single Bonds) 111
5.2 Carbon−Carbon Double Bonds (Olefin Formation) 150
5.3 Reactions that Form Multiple Carbon−Carbon Bonds 166

6 Protecting Groups 168
6.1 Alcohols and Phenols 168
6.2 Amines and Anilines 176
6.3 Aldehydes and Ketones 185

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