10/6/2010. Chapter 6 An Overview of Organic Reactions. Organic Chemical Reactions. 6.1 Kinds of Organic Reactions
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1 John E. McMurry Chapter 6 An Overview of Organic Reactions Richard Morrison University of Georgia, Athens Organic Chemical Reactions Organic chemical reactions broadly organized in two ways: 1. What kinds of reactions occur 2. How those reactions occur 6.1 Kinds of Organic Reactions Addition reactions Occur when two reactants add together to form a single product with no atoms left over Reaction of fumarate with water to yield malate (a step in the citric acid cycle of food metabolism) 1
2 Kinds of Organic Reactions Elimination reactions Occur when a single reactant splits into two products (usually with the formation of a small molecule such as water) Reaction of hydroxybutyryl ACP to yield trans-crotonyl ACP and water (a step in the biosynthesis of fat molecules) Kinds of Organic Reactions Substitution reactions Occur when two reactants exchange parts to give two new products Reaction of an ester such as methyl acetate with water to yield a carboxylic acid and an alcohol In biological pathways this type of reaction occurs in the metabolism of dietary fats Kinds of Organic Reactions Rearrangement reactions Occur when a single reactant undergoes a reorganization of bonds and atoms to yield an isomeric product Rearrangement of dihydroxyacetone phosphate into its constitutional isomer glyceraldehyde 3-phosphate (a step in the metabolism of carbohydrates) 2
3 6.2 How Organic Reactions Occur: Mechanisms Reaction Mechanism An overall description of how a reaction occurs at each stage of a chemical transformation Which bonds are broken and in what order Which bonds are formed and in what order What is the relative rate of each step A complete mechanism accounts for all reactants consumed and all products formed How Organic Reactions Occur: Mechanisms All chemical reactions involve bond breaking and bond making Two ways a covalent two-electron bond can break: 1. Symmetrical One electron remains with each product fragment 2. Unsymmetrical Both bonding electrons remain with one product fragment, leaving the other with a vacant orbital Half-headed arrow, fishhook, indicates movement of one electron Full-headed arrow indicates movement of two electrons How Organic Reactions Occur: Mechanisms Two ways a covalent two-electron bond can form: 1. Symmetrical One electron is donated to the new bond by each reactant (radical) 2. Unsymmetrical Both bonding electrons are donated by one reactant (polar) 3
4 How Organic Reactions Occur: Mechanisms Radical reaction Process that involves symmetrical bond breaking and bond making Radical (free radical) A neutral chemical species that contains an odd number of electrons and has a single, unpaired electron in one of its orbitals Polar reactions Process that involves unsymmetrical bond breaking and bond making Involve species that have an even number of electrons (have only electron pairs in their orbitals) Common in both organic and biological chemistry 6.3 Radical Highly reactive because it contains an atom with an odd number of electrons (usually seven) in a valence shell Can achieve a valence shell octet through: Radical substitution reaction Radical abstracts an atom and one bonding electron from another reactant Radical addition reaction A reactant radical adds to a double bond, taking one electron from double bond and leaving one behind to form a new radical 4
5 Industrial radical reaction The chlorination of methane to yield chloromethane A substitution reaction First step in the preparation of the solvents dichloromethane (CH 2 Cl 2 ) and chloroform (CHCl 3 ) Radical chlorination of methane requires three kinds of steps: initiation, propagation, and termination 1. Initiation Ultraviolet light breaks Cl-Cl bond to generate chlorine radicals 2. Propagation Reaction with CH 4 to generate new radicals and propagate the chain reaction 5
6 3. Termination Two radicals combine to end the chain reaction No new radical species is formed Biological radical reaction Prostaglandin synthesis initiated by abstraction of a hydrogen atom from arachidonic acid. The carbon radical reacts with O 2 to give an oxygen radical Oxygen radical reacts with C=C bond (several steps) Prostaglandin H 2 produced 6
2/28/2011. Chapter 6 An Overview of Organic Reactions. Organic Chemical Reactions. 6.1 Kinds of Organic Reactions
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