Chapter05- An Overview of Organic Reactions

Chapter05- An Overview of Organic Reactions - 5 An...

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McMurry Organic Chemistry 6th edition Chapter 5 1 5. An Overview of Organic Reactions Based on McMurry’s Organic Chemistry , 6 th edition, Chapter 5 ©2003 Ronald Kluger Department of Chemistry University of Toronto
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McMurry Organic Chemistry 6th edition Chapter 5 2 5.1 Kinds of Organic Reactions In general, we look at what occurs and try to learn how it happens Common patterns describe the changes Addition reactions – two molecules combine Elimination reactions – one molecule splits into two Substitution – parts from two molecules exchange Rearrangement reactions – a molecule undergoes changes in the way its atoms are connected
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McMurry Organic Chemistry 6th edition Chapter 5 3 5.2 How Organic Reactions Occur: Mechanisms In a clock the hands move but the mechanism behind the face is what causes the movement In an organic reaction, we see the transformation that has occurred. The mechanism describes the steps behind the changes that we can observe Reactions occur in defined steps that lead from reactant to product
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McMurry Organic Chemistry 6th edition Chapter 5 4 Steps in Mechanisms We classify the types of steps in a sequence A step involves either the formation or breaking of a covalent bond Steps can occur in individually or in combination with other steps When several steps occur at the same time they are said to be concerted
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McMurry Organic Chemistry 6th edition Chapter 5 5 Types of Steps in Reaction Mechanisms Formation of a covalent bond Homogenic or heterogenic Breaking of a covalent bond Homogenic or heterogenic Oxidation of a functional group Reduction of a functional group
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McMurry Organic Chemistry 6th edition Chapter 5 6 Homogenic Formation of a Bond One electron comes from each fragment No electronic charges are involved Not common in organic chemistry
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McMurry Organic Chemistry 6th edition Chapter 5 7 Heterogenic Formation of a Bond One fragment supplies two electrons One fragment supplies no electrons Combination can involve electronic charges Common in organic chemistry
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McMurry Organic Chemistry 6th edition Chapter 5 8 Homolytic Breaking of Covalent Bonds Each product gets one electron from the bond Not common in organic chemistry
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McMurry Organic Chemistry 6th edition Chapter 5 9 Heterolytic Breaking of Covalent Bonds Both electrons from the bond that is broken become associated with one resulting fragment A common pattern in reaction mechanisms
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McMurry Organic Chemistry 6th edition Chapter 5 10 Indicating Steps in Mechanisms Curved arrows indicate breaking and forming of bonds Arrowheads with a “half” head (“fish-hook”) indicate homolytic and homogenic steps (called ‘radical processes’) Arrowheads with a complete head indicate heterolytic and heterogenic steps (called ‘polar processes’)
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McMurry Organic Chemistry 6th edition Chapter 5 11 Radicals Alkyl groups are abbreviate “R” for radical
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