Książki

Teaches and enables students to build confidence in drawing and manipulating curly arrows, a fundamental skill for all organic chemists


This book is an interactive approach to learning about chemistry of the carbonyl group-inviting students to work through its pages with pencil and paper in hand. It educates with the belief that the most effective way to learn is by practice and interaction. With this in mind, the reader is asked to predict what would happen under a specific set of reaction conditions. The book is divided into frames: each frame poses a question and invites the reader to predict what will happen. Subsequent frames give the solution but then pose more questions to develop a theme further.


Chemistry of the Carbonyl Group: A Programmed Approach to Organic Reaction Mechanisms, Revised Edition provides a solid grounding in the fundamental reactions of carbonyls. Presented in full colour to enhance the understanding of mechanisms within chemistry, the chapters of this step-by-step guide cover: nucleophilic addition to the carbonyl group; nucleophilic substitution; nucleophilic substitution at the carbonyl group with complete removal of carbonyl oxygen; carbanions and enolisation; and building organic molecules from carbonyl compounds.





A must-have book for undergraduate chemists to emphasise understanding in carbonyl group chemistry

Goes through all the stages of basic carbonyl chemistry, detailing even the simplest mechanisms

A step-by-step learning guide to synthetic chemistry for the first year of a chemistry degree, with all the information needed for independent learning

Provides a solid grounding in the fundamental reactions of carbonyls which will inform the understanding of many other organic chemistry reactions



Chemistry of the Carbonyl Group: A Programmed Approach to Organic Reaction Mechanisms - Revised Edition is packed with all the information on synthetic chemistry that every first-year student will need in order to learn independently.

Chemistry of the Carbonyl Group - A Step-by-Step Approach to Understanding Organic Reaction Mechanisms - Revised Edition

PREFACE xi





ACKNOWLEDGEMENTS xiii





SOME HELP THAT YOU MAY NEED xv





WHAT DO YOU NEED TO KNOW BEFORE YOU START? xvii





INTRODUCTION xix





1 Nucleophilic Addition to the Carbonyl Group 1





Nucleophilic addition: what it is and how it happens 3





Alcohols as nucleophiles: acetal formation 6





Some carbon-carbon bond-forming reactions with carbon nucleophiles: cyanide ion, acetylide ion and Grignard reagents 10





Hydride ion and its derivatives LiAlH4 and NaBH4. Reduction of aldehydes and ketones 17





Meerwein-Ponndorf reduction and Oppenauer oxidation, with a branch program on how to draw transition states 19





Two general revision problems 25





2 Nucleophilic Substitution 29





Substitution: how it happens 31





LiAlH4 reduction of esters 33





Reaction of Grignard reagents with esters 34





Alkaline hydrolysis of esters 38





Acid hydrolysis of amides 39





Summary of acid and base catalysis 41





Reaction between carboxylic acids and thionyl chloride 41





Synthesis of esters and anhydrides from carboxylic acids 43





Review questions 45





3 Nucleophilic Subsitution at the Carbonyl Group with Complete Removal of Carbonyl Oxygen 49





Imine formation from aldehydes and ketones 51





Oxime formation and the structure of oximes 53





Hydrazone and semicarbazone formation 54





Reduction of C=O to CH2 56





Conversion of C=O to CCl2 60





DDT synthesis 64





Chloromethylation of aromatic compounds 65





Review questions 66





4 Carbanions and Enolisation 69





Carbanions 71





Tautomerism 72





Equilibration and racemisation of ketones by enolisation 73





Halogenation of ketones 78





Formation of bromo-acid derivatives 83





Organo-zinc derivatives and their use in synthesis 85





Review questions 87





5 Building Organic Molecules from Carbonyl Compounds 89





Using enols as nucleophiles to attack other carbonyl groups 92





The aldol reaction 92





The Claisen ester condensation 93





Acid catalysed condensation of acetone 94





Self-condensation reactions 96





Elaboration of a skeleton in synthesis 97





Cross-condensations with molecules which cannot enolise 98





Mannich reaction 103





Perkin reaction 105





Stable enols from -dicarbonyl compounds 108





Knoevenagel reaction 110





Alkylation of -dicarbonyl compounds 113





Michael reaction 116





Decarboxylation 125





Base cleavage of -dicarbonyl compounds 131





Cyclisation reactions: the Dieckmann condensation 134





Cyclisation of diketones 136





The dimedone synthesis 137





Ring opening by base cleavage of -dicarbonyl compounds 141





Revision questions 142





Examples of syntheses: two steroid syntheses 145





Stork's cedrene synthesis 150





INDEX 155