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.
By:
Timothy K. Dickens,
Stuart Warren (Cambridge University,
UK)
Imprint: John Wiley & Sons Inc
Country of Publication: United States
Edition: Revised Edition
Dimensions:
Height: 213mm,
Width: 137mm,
Spine: 13mm
Weight: 272g
ISBN: 9781119459569
ISBN 10: 1119459567
Pages: 192
Publication Date: 22 June 2018
Audience:
College/higher education
,
A / AS level
Format: Paperback
Publisher's Status: Active
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 β-dicarbonyl compounds 108 Knoevenagel reaction 110 Alkylation of β-dicarbonyl compounds 113 Michael reaction 116 Decarboxylation 125 Base cleavage of β-dicarbonyl compounds 131 Cyclisation reactions: the Dieckmann condensation 134 Cyclisation of diketones 136 The dimedone synthesis 137 Ring opening by base cleavage of β-dicarbonyl compounds 141 Revision questions 142 Examples of syntheses: two steroid syntheses 145 Stork’s cedrene synthesis 150 Index 155
TIMOTHY K. DICKENS, FRSC, is Official Fellow, College Lecturer and Director of Studies in Chemistry at Peterhouse, Cambridge. Dr Dickens graduated from the University of Kent in 1982, and, after two years' research at Oxford, he joined Glaxo where he spent 24 years in both scientific and technology senior roles. In 2008, he joined the University of Cambridge, where his research has focused on Ring Currents in conjugated systems. STUART WARREN, PHD, is the author of the textbooks Organic Chemistry, Organic Synthesis: The Disconnection Approach and Organic Synthesis. He retired from Churchill College, Department of Chemistry, University of Cambridge in 2006, having fostered some of the most successful organic chemistry academics in the UK.
