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Organic Reaction Mechanism : Through Problem Solving Approach Nitin D Gaikwad (M.Sc., Ph.D.) Assistant Professor Department of Chemistry, K.T.H.M College, Nashik-422005 Maharashtra, India email :gaikwad.chemistry@gmail.com Organic Reaction Mechanism: Through Problem Solving Approach ISBN : 978-93-5267-423-7 All rights reserved No part of this book may be reproduced in any form, byphotostat, microfilm, xerography or any other means or incorporated into any information retrieval system, electronic or mechanical, without the written permission of the copyright owner PREFACE This book aims to teach students how to draw organic reaction mechanism for themselves Almost all available books, on organic reaction mechanism describe reactions and their conversions This book confronts the student with the organic reaction mechanism by showing how the reagent and starting molecule act together in the reaction The reaction mechanism approach is learnt by students from this book who then teaches themselves how to use mechanism by solving a series of problems It is not a conventional text book with detailed text explanation In short this book understand quickly and giving information about reaction mechanism Also the student has planned sequence of problems to demonstrate the use of each new mechanism and to test his understanding of it Each problem is followed by possible reaction mechanism and short explanation, So that if the student fails to solve a problem he will still understand the answer better for having attempted the problem himself The student therefore has the possibility of continuous self assessment through the use of large number of problems There are some excellent books written about organic reaction mechanism but they mostly present complete synthesis not reaction mechanism I have tried in this book to teach student to speak the language of reaction mechanism themselves This book is originally written for the first year students The programme aims to allow students to teach themselves but it shouldn’t mean any less work for them Because students discover what they don’t know, they should have more sensible questions to ask when they were solving reaction mechanism My aim is to give you more time for real teaching The book should the ground work and you should be able to set suitable programme and discuss then profitably The book itself has plenty of problems of this sort Though the programme may introduce you reaction mechanism, its main aim is to suggest a mechanistic approach to the organic reactions You therefore need to have a reasonable grounding in organic chemistry so that you are familiar with most basic organic reactions If you are first year student with no much experience of organic chemistry or limited knowledge of organic reactions in practice you will probably be able to work straight through the book to learn the actual reaction mechanism The point of book learning is that you learn at your own pace and that you yourself check on your own progress Contents 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 Nitration Reaction Nucleophilic Substitution by NGP Aromatic Nucleophilic Substitution Halo-hydroxylation Reaction and Aliphatic Nucleophilic Substitution Neighbouring Group Participation by sigma bond Aromatic Electrophilic Substitution and Diazotization Aromatic Nucleophilic Substitution Addition Reaction Nitration Reaction Aromatic Electrophilic Substitution Neighbouring Group Participation by sigma bond Elimination Reaction with Rearrangement Rearrangement Pyrolytic Elimination Reaction Gattermann Koch Reaction Pinacol Pinacolone Rearrangement Alkylation and Dehydration Reaction Neighbouring Group Participation by heteroatom Aromatic Nucleophilic Substitution and condensation Aromatic Electrophilic Substitution Addition Reaction Methylation and Vilsmeyer Haack Formylation Reaction Elimination and Addition Reaction Aromatic Nucleophilic Substitution 25 26 27 28 29 Neighbouring Group Participation by sigma bond Diazotization Reaction with stereochemistry Friedel Craft Acylation and Condensation Reaction Addition Reaction: Bromination Rearrangement 30 Aliphatic Nucleophilic Substitution and Chlorination by SNi mechanism Aliphatic Nucleophilic Substitution Jacobson’s Reaction NGP by Aryl ring 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 Elimination Reaction by E2 Mechanism Cyclisation by protonation Cyclisation by using PTSA Aromatic Nucleophilic Substitution by Elimination –Addition Mechanism Diazotization Reaction with stereochemistry Neighbouring Group Participation by heteroatom and Aliphatic Nucleophilic Substitution Friedel Craft Alkylation Reaction and Aromatization Reaction Riemann Tiemann Reaction SN2 Mechanism N-Acylation and Nitration Reaction Addition Reaction Aromatic Nucleophilic Substitution by Elimination –Addition Mechanism and Diazo coupling reaction Grignard Reaction Halogenation Reaction and amide formation Elimination and Addition Reaction 49 Dehydration and Epoxidation Reaction 50 Aliphatic Nucleophilic Substitution and Chlorination by SNi 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 mechanism and SN2 Mechanism Friedel Craft Acylation and Clemmensons Reduction Nitration ans N-Acylation Reaction Chlorination with stereochemistry and Elimination Reaction by Saytzeff rule Diazotization Reaction with stereochemistry and oxime formation Hydroboration – Oxidation Reaction SNi Mechanism Nitration and Aromatic Nucleophilic Substitution Halogenation and Nitration Reaction Aromatic Electrophilic Substitution Vilsmeyer Haack Formylation Reaction Friedel Craft Acylation Reaction Hunds Dicker Reaction Oxidation and Nitration Reaction Aldol Condensation Reaction Epoxidation and Hydrolysis Vilsmeyer Haack Formylation Reaction Halogenation Reaction and Neighbouring Group Participation by Pi bond Halogenation: Aromatic Electrophilic Substitution Halogenation: Aromatic Electrophilic Substitution Methylation and Nitration Reaction Rearrangement Diazotisation and Diazo coupling Reaction Rearrangement 73 74 75 76 77 78 79 80 81 82 83 84 Pyrolytic Elimination Reaction Vilsmeyer Haack Formylation Reaction Dehydration: Elimination Reaction Aliphatic Nucleophilic substitution: Chlorination Cyclisation Aliphatic Nucleophilic substitution Aromatic Electrophilic Substitution Phase Transfer Catalyst Addition and Elimination Reaction Methylation , Oxidation and Hydrolysis Aliphatic Nucleophilic substitution and Reduction Halogenation: addition Reaction with Stereochemistry 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 Elimination Reaction (E2) Alkylation Reaction Iodination Reaction Addition Reaction Through Rearrangement Friedel Craft Alkylation Reaction Aromatic Electrophilic Substitution Friedel Craft Acylation Reaction and Bromination reaction Pyrolytic Elimination Reaction Sulphonation and Nitration Reaction Aromatic Nucleophilic Substitution Nitration and Oxidation Reaction Sandmeyer Reaction Pyrolytic Elimination Reaction Diazotization and Neighbouring Group Participation Dehydration: Elimination Reaction Neighbouring Group Participation with Stereochemistry 109 110 111 112 113 114 115 116 117 118 119 Benzyne Formation Ortho Nitration reaction Grignard Reaction Friedel Craft Acylation Reaction and Clemmensons Reduction Elimination Reaction Addition Reaction Neighbouring Group Participation by Hetero atom and Grignard Reagent Elimination Reaction and Neighbouring Group Participation by Aryl ring Cyclisation Nitration Reaction Dehydration and Elimination Reaction Elimination Reaction with Stereochemistry Methylation and o-Nitration Bromination and Elimination Reaction Elimination and Epoxidation Reaction Addition and Cyclisation Reaction Neighbouring Group Participation by Aryl ring Pyrolytic Elimination Reaction Acid Hydrolysis reaction 120 121 122 123 124 125 126 Elimination Reaction: E2 Aliphatic Nucleophilic substitution and Catalytic Reduction N-Acylation and Nitration Reaction Friedel Craft Alkylation, Oxidation and Halogenation Addition and Rearrangement Reaction Dehydration and Hydroxylation Reaction Grignard Reagent and Dehydration 101 102 103 104 105 106 107 108 Nitration Reaction 10 Aromatic Electrophilic Substitution 11 Neighbouring Group Participation by sigma bond 12 Elimination Reaction with Rearrangement 13 Rearrangement 14 Pyrolytic Elimination Reaction 15 Gattermann Koch Reaction 16 Pinacol Pinacolone Rearrangement 17 Alkylation and Dehydration Reaction 18 Neighbouring Group Participation by heteroatom 19 Aromatic Nucleophilic Substitution and condensation 20 Aromatic Electrophilic Substitution 21 Addition Reaction 22 Methylation and Vilsmeyer Haack Formylation Reaction .. .Organic Reaction Mechanism : Through Problem Solving Approach Nitin D Gaikwad (M.Sc., Ph .D.) Assistant Professor Department of Chemistry, K.T.H.M... email :gaikwad. chemistry@gmail.com Organic Reaction Mechanism: Through Problem Solving Approach ISBN : 978-93-5267-423-7 All rights reserved No part of this book may be reproduced in any form, byphotostat,... organic reaction mechanism for themselves Almost all available books, on organic reaction mechanism describe reactions and their conversions This book confronts the student with the organic reaction