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<blockquote data-quote="MaD-DoC" data-source="post: 1304579" data-attributes="member: 56284"><p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"> <strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">nucleophilic substitution</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: A nucleophilic reagent replaces an atom or group of atoms in another molecule. </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">e.g. halogenoalkanes react with electron pair donating reagents (see <strong> nucleophilic attack </strong>above).</span></span> </p> </li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">polar bond</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: A covalent bond in which the two atoms have different electronegativities leading to an unequal sharing of the bonding pair(s) of electrons. </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-size: 10px"><span style="font-family: 'Comic Sans MS'">e.g. a carbon-chlorine bond <strong>C</strong></span><strong><span style="font-family: 'Comic Sans MS'">δ</span></strong><span style="font-family: 'Comic Sans MS'"><strong>+-Cl</strong></span><strong><span style="font-family: 'Comic Sans MS'">δ</span></strong><span style="font-family: 'Comic Sans MS'"><strong>- </strong>or the carbon-oxygen double bond (carbonyl) ><strong>C</strong></span><strong><span style="font-family: 'Comic Sans MS'">δ</span></strong><span style="font-family: 'Comic Sans MS'"><strong>+=O</strong></span><strong><span style="font-family: 'Comic Sans MS'">δ</span></strong><span style="font-family: 'Comic Sans MS'"><strong>-</strong> </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">See <strong> Pauling electronegativity</strong> scale above.</span></span> </p> </li> </ul></li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> primary </span></span> </strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">(prim or 1o): A structural term in organic chemistry to indicate no or just one alkyl/aryl group are attached to the <strong><span style="color: #0000ff"> carbon</span></strong> or <strong><span style="color: #0000ff"> nitrogen</span></strong> atom of the functional group e.g. </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> bromomethane <span style="color: #0000ff"> C</span>H3Br</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> and 1-chloropropane <strong> CH3CH2<span style="color: #0000ff">C</span>H2Cl</strong> are primary halogenoalkanes</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> methylamine CH3<span style="color: #0000ff">N</span>H2 </span></span> </strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> and propylamine <strong> CH3CH2CH2<span style="color: #0000ff">N</span>H2 </strong> are primary aliphatic amines</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">methanol <span style="color: #0000ff"> C</span>H3OH</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> and <strong> butan-1-ol CH3CH2CH2<span style="color: #0000ff">C</span>H2OH</strong> are primary alcohols</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"><span style="color: #0000ff"> C</span></span></span><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">H3+ </span></span> </strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> and <strong> CH3CH2<span style="color: #0000ff">C</span>H2+ </strong> are primary carbocations</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">see also <strong> secondary</strong> and <strong>tertiary</strong> for comparison</span></span> </p> </li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">propagation step</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: Type of mechanism step in free radical chain reactions, where a radical reacts with a substrate molecule, but also/only produces another reactive free radical which continues the reaction .e.g. </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">CH3. + Cl2 </span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> ==><strong> CH3Cl + .Cl </strong> </span></span> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> (which produces the product in the chlorination of methane AND a reactive chlorine radical)</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">RO-CH2-CH2. + CH2=CH2 </span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> ==><strong> RO-CH2-CH2-CH2-CH2. </strong> </span></span> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> (in the free radical polymerization of alkenes, a peroxide radical adds to an alkene (1st reactant on left) and this radical adds to another alkene molecule (right product) which is itself a radical and continue reaction building up the polymer chain until terminated!)</span></span> </p> </li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">protonation</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: Adding a proton, H+, to a species e.g. </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">CH2=CH2 + H2SO4 </span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> ==><strong> CH3-CH2+ + HSO4-</strong></span></span> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> (in the electrophilic addition of sulphuric acid to alkenes)</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">CH3CH2OH + H3O+ </span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> ==><strong> CH3CH2OH2+ + H2O</strong></span></span> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> (in the OH substituted reactions of alcohols)</span></span> </p> </li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">quaternary </span></span> </strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">(quat or 4o): The term used to describe the alkylammonium salts formed when <span style="color: #0000ff"><strong> nitrogen</strong></span> is bonded to four alkyl groups i.e. all four hydrogens on the ammonium ion are replaced by alkyl groups.</span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">[(CH3)4<span style="color: #0000ff">N</span>]+Cl-</span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> is tetramethylammonium chloride, and can be formed by multiple nucleophilic substitutions happen when e.g. bromoethane is reacted with ammonia.</span></span> </p> </li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"> <strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">secondary </span></span> </strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">(sec or 2o): A structural term in organic chemistry to indicate two alkyl/aryl groups are attached to the <strong><span style="color: #0000ff"> carbon</span></strong> or <strong><span style="color: #0000ff"> nitrogen</span></strong> atom of the functional group e.g. </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> 2-chloropropane CH3<span style="color: #0000ff">C</span>HClCH3 </span></span> </strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> is a secondary halogenoalkane</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> diethylamine (CH3CH2)2<span style="color: #0000ff">N</span>H</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> is a secondary aliphatic amine</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">CH3<span style="color: #0000ff">C</span>H+CH3 </span></span> </strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> is a secondary carbocation</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> butan-2-ol CH3CH2<span style="color: #0000ff">C</span>HOHCH3</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> is a secondary alcohol</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">see also <strong> primary</strong> and <strong>tertiary</strong> for comparison</span></span></p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">shift of electrons</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: see use of <strong>arrows</strong> in mechanisms</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> SN1</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: Shorthand for a nucleophilic substitution reaction in which the rate determining step is the formation of carbocation from just one of the reactant molecules or intermediates (<strong>X</strong>) and the rate is independent any other reactant or intermediate. </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> This results in overall <strong> 1st order reaction kinetics</strong>: e.g. <strong>rate = k1[X]</strong> </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">and sometimes referred to as a '<strong>unimolecular</strong>' reaction. (see <strong>mechanisms Part II</strong>)</span></span> </p> </li> </ul></li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> SN2</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: Shorthand for a nucleophilic substitution reaction in which the rate determining step is a bimolecular collision of two reactant molecules (<strong>X</strong> and <strong>Y</strong>) and the rate is independent any other reactant or intermediate. </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> This results in overall <strong> 2nd order reaction kinetics</strong>: e.g. <strong>rate = k2[X][Y]</strong> </span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">and sometimes referred to as a '<strong>bimolecular</strong>' reaction. (see <strong>mechanisms Part II</strong>)</span></span> </p> </li> </ul></li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> stereospecific/stereospecificity</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: means the change <strong>reactants ==> products</strong> is <strong>dependent in some way on the spatial orientation</strong> of at least one of the reactants or intermediates, e.g. in the key-lock mechanism of enzymes, the 'key into lock' interaction, i.e. the stereospecificity of enzymes, partly depends on the spatial orientation of the enzyme's protein structure and the shape of the substrate molecule, particularly from the point of view of bond formation or the inter-molecular force of hydrogen bonding.</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">steric hindrance</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: This means a reaction is inhibited because of some spatial/orientation limitation, e.g. bulky groups attached to an atom/bond that theoretically is susceptible to attack by a particular reagent.</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">substitution</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: When one atom or group of atoms is replaced by another atom or group of atoms. (see <strong>mechanism index</strong> for lots of examples)</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">symmetrical alkene</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: An alkene in which the groups attached to each carbon of the double bond are identical. (see <strong>alkene mechanisms</strong>) e.g.</span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> ethene <strong>H2C=CH2</strong> or but-2-ene <strong>CH3-CH=CH-CH3</strong> </span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">If an unsymmetrical reagent e.g. <strong>HX</strong> is added, <strong>only one product</strong> is formed.</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">e.g. <strong>CH3-CH2X</strong> or <strong>CH3-CH2-CHX-CH3</strong> from ethene or but-2-ene.</span></span> </p> </li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"> <strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">termination step</span></span> </strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> : A step in a free radical chain reaction in which two radicals combine to bring that particular 'chain' to a halt.</span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">e.g. in the chlorination of methane two methyl radicals can combine to form ethane. (see <strong>mechanisms Part Ia</strong>)</span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">2H3C<span style="color: #ff0000">.</span> </span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">==><strong> H3C-CH3 </strong></span></span> </p> </li> </ul></li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> tertiary</span></span> </strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">(tert or 3o): A structural term in organic chemistry to indicate three alkyl or aryl groups are attached to the <strong><span style="color: #0000ff"> carbon</span></strong> or <strong><span style="color: #0000ff"> nitrogen</span></strong> atom of the functional group e.g.</span></span> </p> <ul> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> 2-chloro-2-methylpropane (CH3)3<span style="color: #0000ff">C</span>Cl</span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> is a tertiary halogenoalkane</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> trimethylamine (CH3)3<span style="color: #0000ff">N</span>:</span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> is a tertiary aliphatic amine</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> 2-methylpropan-2-ol (CH3)3<span style="color: #0000ff">C</span>OH</span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> is a tertiary alcohol</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">(CH3)2<span style="color: #0000ff">C</span>+CH2CH3 </span></span> </strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> is a tertiary carbocation</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">see also <strong> primary</strong> and <strong>secondary</strong> for comparison</span></span> </p> </li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">transition state</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: see <strong> activated complex</strong> above</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> 'unimolecular' </span></span> </strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">mechanism/kinetics : <strong> see SN1</strong></span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">unsymmetrical alkene</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: structure and addition to, see <strong>non-symmetrical alkene</strong></span></span> </p> </li> </ul> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">I hope this page will help with the following GCE-AS-A2-IB Advanced/Subsidiary Level Chemistry syllabuses</span></span> </strong> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">Salters Chemistry:</span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> Chemistry 3887/7887 5.3.20 Organic Reaction Mechanisms, unit/module A Atmosphere, PR Polymer Revolution, What's in a Medicine, MD Medicine by Design</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">OCR Chemistry:</span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> 3882/7882 module 2812 Chains and Rings, 2814 Chains, Rings and Spectroscopy</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">Edexcel Chemistry</span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> 8080/8090 Topic 2.2 Organic Chemistry I (Introduction, alkanes, alkenes, halogenoalkanes), Topic 4.5 Organic Chemistry II (acids, esters, carbonyl compounds, acid chlorides, nitrogen compounds, and further halogeno-compounds, Topic 5.3 Organic chemistry III (reaction mechanisms and aromatic compounds)</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">Nuffield Chemistry:</span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> 8086/9086 Unit 1 Introductory Chemistry Topic 2 Alcohols: an introduction to organic chemistry, Unit 2 Bonding and reactions: Topic 8 Organic Chemistry: Hydrocarbons, Topic 10 Halogenoalkanes (haloalkanes), Unit 4 Energy and reactions: Topic 12 Arenes: benzene and phenol</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">AQA Chemistry:</span></span></strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> 5421/6421 Module 3 Introduction to Organic Chemistry/Practical: Chlorination alkanes, alkene reactions, haloalkanes, alcohols; Module 4 Further Physical and Organic Chemistry: aldehydes and ketones reactions, carboxylic acids and esters, acylation, aromatic chemistry, amines</span></span> </p> </li> <li data-xf-list-type="ul"> <p style="text-align: left"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> International Baccalaureate Chemistry</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: Topic 16 Kinetics: 16.2 Reaction Mechanism; Topic 20 Organic Chemistry: 20.2 Hydrocarbons, 20.3 Nucleophilic substitution reactions, 20.4 Alcohols; Option A Higher Physical Organic Chemistry A.3 Reaction Mechanism, A.4 Nucleophilic substitution reactions; Option E Chemical Industries: Topic E.8 Mechanisms in the Organic Chemicals Industry; Option H Further Organic Chemistry: H.2 Free Radical Substitution Reactions, H.3 Electrophilic Addition Reactions, H.4 Electrophilic Substitution Reactions, H.5 Nucleophilic Addition Reactions, H.6 Nucleophilic Substitution Reactions, H.7 Elimination Reactions, H.8 Addition-elimination Reactions.</span></span></p> </li> </ul><p> <img src="http://books.google.com/images/cleardot.gif" alt="" class="fr-fic fr-dii fr-draggable " style="" /></blockquote><p></p>
[QUOTE="MaD-DoC, post: 1304579, member: 56284"] [LIST] [*] [LEFT] [B][FONT=Comic Sans MS][SIZE=2]nucleophilic substitution[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: A nucleophilic reagent replaces an atom or group of atoms in another molecule. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]e.g. halogenoalkanes react with electron pair donating reagents (see [B] nucleophilic attack [/B]above).[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]polar bond[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: A covalent bond in which the two atoms have different electronegativities leading to an unequal sharing of the bonding pair(s) of electrons. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][SIZE=2][FONT=Comic Sans MS]e.g. a carbon-chlorine bond [B]C[/B][/FONT][B][FONT=Comic Sans MS]δ[/FONT][/B][FONT=Comic Sans MS][B]+-Cl[/B][/FONT][B][FONT=Comic Sans MS]δ[/FONT][/B][FONT=Comic Sans MS][B]- [/B]or the carbon-oxygen double bond (carbonyl) >[B]C[/B][/FONT][B][FONT=Comic Sans MS]δ[/FONT][/B][FONT=Comic Sans MS][B]+=O[/B][/FONT][B][FONT=Comic Sans MS]δ[/FONT][/B][FONT=Comic Sans MS][B]-[/B] [/FONT][/SIZE] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]See [B] Pauling electronegativity[/B] scale above.[/SIZE][/FONT] [/LEFT] [/LIST] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] primary [/SIZE][/FONT] [/B][FONT=Comic Sans MS][SIZE=2](prim or 1o): A structural term in organic chemistry to indicate no or just one alkyl/aryl group are attached to the [B][COLOR=#0000ff] carbon[/COLOR][/B] or [B][COLOR=#0000ff] nitrogen[/COLOR][/B] atom of the functional group e.g. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] bromomethane [COLOR=#0000ff] C[/COLOR]H3Br[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2] and 1-chloropropane [B] CH3CH2[COLOR=#0000ff]C[/COLOR]H2Cl[/B] are primary halogenoalkanes[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] methylamine CH3[COLOR=#0000ff]N[/COLOR]H2 [/SIZE][/FONT] [/B] [FONT=Comic Sans MS][SIZE=2] and propylamine [B] CH3CH2CH2[COLOR=#0000ff]N[/COLOR]H2 [/B] are primary aliphatic amines[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]methanol [COLOR=#0000ff] C[/COLOR]H3OH[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2] and [B] butan-1-ol CH3CH2CH2[COLOR=#0000ff]C[/COLOR]H2OH[/B] are primary alcohols[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2][COLOR=#0000ff] C[/COLOR][/SIZE][/FONT][FONT=Comic Sans MS][SIZE=2]H3+ [/SIZE][/FONT] [/B] [FONT=Comic Sans MS][SIZE=2] and [B] CH3CH2[COLOR=#0000ff]C[/COLOR]H2+ [/B] are primary carbocations[/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]see also [B] secondary[/B] and [B]tertiary[/B] for comparison[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]propagation step[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: Type of mechanism step in free radical chain reactions, where a radical reacts with a substrate molecule, but also/only produces another reactive free radical which continues the reaction .e.g. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]CH3. + Cl2 [/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] ==>[B] CH3Cl + .Cl [/B] [/SIZE][/FONT] [FONT=Comic Sans MS][SIZE=2] (which produces the product in the chlorination of methane AND a reactive chlorine radical)[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]RO-CH2-CH2. + CH2=CH2 [/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2] ==>[B] RO-CH2-CH2-CH2-CH2. [/B] [/SIZE][/FONT] [FONT=Comic Sans MS][SIZE=2] (in the free radical polymerization of alkenes, a peroxide radical adds to an alkene (1st reactant on left) and this radical adds to another alkene molecule (right product) which is itself a radical and continue reaction building up the polymer chain until terminated!)[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]protonation[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: Adding a proton, H+, to a species e.g. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]CH2=CH2 + H2SO4 [/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2] ==>[B] CH3-CH2+ + HSO4-[/B][/SIZE][/FONT] [FONT=Comic Sans MS][SIZE=2] (in the electrophilic addition of sulphuric acid to alkenes)[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]CH3CH2OH + H3O+ [/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2] ==>[B] CH3CH2OH2+ + H2O[/B][/SIZE][/FONT] [FONT=Comic Sans MS][SIZE=2] (in the OH substituted reactions of alcohols)[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]quaternary [/SIZE][/FONT] [/B][FONT=Comic Sans MS][SIZE=2](quat or 4o): The term used to describe the alkylammonium salts formed when [COLOR=#0000ff][B] nitrogen[/B][/COLOR] is bonded to four alkyl groups i.e. all four hydrogens on the ammonium ion are replaced by alkyl groups.[/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2][(CH3)4[COLOR=#0000ff]N[/COLOR]]+Cl-[/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] is tetramethylammonium chloride, and can be formed by multiple nucleophilic substitutions happen when e.g. bromoethane is reacted with ammonia.[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT] [B][FONT=Comic Sans MS][SIZE=2]secondary [/SIZE][/FONT] [/B][FONT=Comic Sans MS][SIZE=2](sec or 2o): A structural term in organic chemistry to indicate two alkyl/aryl groups are attached to the [B][COLOR=#0000ff] carbon[/COLOR][/B] or [B][COLOR=#0000ff] nitrogen[/COLOR][/B] atom of the functional group e.g. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] 2-chloropropane CH3[COLOR=#0000ff]C[/COLOR]HClCH3 [/SIZE][/FONT] [/B] [FONT=Comic Sans MS][SIZE=2] is a secondary halogenoalkane[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] diethylamine (CH3CH2)2[COLOR=#0000ff]N[/COLOR]H[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2] is a secondary aliphatic amine[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]CH3[COLOR=#0000ff]C[/COLOR]H+CH3 [/SIZE][/FONT] [/B] [FONT=Comic Sans MS][SIZE=2] is a secondary carbocation[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] butan-2-ol CH3CH2[COLOR=#0000ff]C[/COLOR]HOHCH3[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2] is a secondary alcohol[/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]see also [B] primary[/B] and [B]tertiary[/B] for comparison[B][/B][/SIZE][/FONT][/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]shift of electrons[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: see use of [B]arrows[/B] in mechanisms[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] SN1[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: Shorthand for a nucleophilic substitution reaction in which the rate determining step is the formation of carbocation from just one of the reactant molecules or intermediates ([B]X[/B]) and the rate is independent any other reactant or intermediate. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2] This results in overall [B] 1st order reaction kinetics[/B]: e.g. [B]rate = k1[X][/B] [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]and sometimes referred to as a '[B]unimolecular[/B]' reaction. (see [B]mechanisms Part II[/B])[/SIZE][/FONT] [/LEFT] [/LIST] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] SN2[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: Shorthand for a nucleophilic substitution reaction in which the rate determining step is a bimolecular collision of two reactant molecules ([B]X[/B] and [B]Y[/B]) and the rate is independent any other reactant or intermediate. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2] This results in overall [B] 2nd order reaction kinetics[/B]: e.g. [B]rate = k2[X][Y][/B] [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]and sometimes referred to as a '[B]bimolecular[/B]' reaction. (see [B]mechanisms Part II[/B])[/SIZE][/FONT] [/LEFT] [/LIST] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] stereospecific/stereospecificity[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: means the change [B]reactants ==> products[/B] is [B]dependent in some way on the spatial orientation[/B] of at least one of the reactants or intermediates, e.g. in the key-lock mechanism of enzymes, the 'key into lock' interaction, i.e. the stereospecificity of enzymes, partly depends on the spatial orientation of the enzyme's protein structure and the shape of the substrate molecule, particularly from the point of view of bond formation or the inter-molecular force of hydrogen bonding.[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]steric hindrance[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: This means a reaction is inhibited because of some spatial/orientation limitation, e.g. bulky groups attached to an atom/bond that theoretically is susceptible to attack by a particular reagent.[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]substitution[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: When one atom or group of atoms is replaced by another atom or group of atoms. (see [B]mechanism index[/B] for lots of examples)[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]symmetrical alkene[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: An alkene in which the groups attached to each carbon of the double bond are identical. (see [B]alkene mechanisms[/B]) e.g.[/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2] ethene [B]H2C=CH2[/B] or but-2-ene [B]CH3-CH=CH-CH3[/B] [/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]If an unsymmetrical reagent e.g. [B]HX[/B] is added, [B]only one product[/B] is formed.[/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]e.g. [B]CH3-CH2X[/B] or [B]CH3-CH2-CHX-CH3[/B] from ethene or but-2-ene.[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT] [B][FONT=Comic Sans MS][SIZE=2]termination step[/SIZE][/FONT] [/B] [FONT=Comic Sans MS][SIZE=2] : A step in a free radical chain reaction in which two radicals combine to bring that particular 'chain' to a halt.[/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]e.g. in the chlorination of methane two methyl radicals can combine to form ethane. (see [B]mechanisms Part Ia[/B])[/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]2H3C[COLOR=#ff0000].[/COLOR] [/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]==>[B] H3C-CH3 [/B][/SIZE][/FONT] [/LEFT] [/LIST] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] tertiary[/SIZE][/FONT] [/B][FONT=Comic Sans MS][SIZE=2](tert or 3o): A structural term in organic chemistry to indicate three alkyl or aryl groups are attached to the [B][COLOR=#0000ff] carbon[/COLOR][/B] or [B][COLOR=#0000ff] nitrogen[/COLOR][/B] atom of the functional group e.g.[/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] 2-chloro-2-methylpropane (CH3)3[COLOR=#0000ff]C[/COLOR]Cl[/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] is a tertiary halogenoalkane[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] trimethylamine (CH3)3[COLOR=#0000ff]N[/COLOR]:[/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] is a tertiary aliphatic amine[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] 2-methylpropan-2-ol (CH3)3[COLOR=#0000ff]C[/COLOR]OH[/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] is a tertiary alcohol[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2](CH3)2[COLOR=#0000ff]C[/COLOR]+CH2CH3 [/SIZE][/FONT] [/B] [FONT=Comic Sans MS][SIZE=2] is a tertiary carbocation[/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]see also [B] primary[/B] and [B]secondary[/B] for comparison[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]transition state[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: see [B] activated complex[/B] above[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] 'unimolecular' [/SIZE][/FONT] [/B][FONT=Comic Sans MS][SIZE=2]mechanism/kinetics : [B] see SN1[/B][/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]unsymmetrical alkene[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: structure and addition to, see [B]non-symmetrical alkene[/B][/SIZE][/FONT] [/LEFT] [/LIST] [LEFT][B][FONT=Comic Sans MS][SIZE=2]I hope this page will help with the following GCE-AS-A2-IB Advanced/Subsidiary Level Chemistry syllabuses[/SIZE][/FONT] [/B] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]Salters Chemistry:[/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] Chemistry 3887/7887 5.3.20 Organic Reaction Mechanisms, unit/module A Atmosphere, PR Polymer Revolution, What's in a Medicine, MD Medicine by Design[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]OCR Chemistry:[/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] 3882/7882 module 2812 Chains and Rings, 2814 Chains, Rings and Spectroscopy[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]Edexcel Chemistry[/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] 8080/8090 Topic 2.2 Organic Chemistry I (Introduction, alkanes, alkenes, halogenoalkanes), Topic 4.5 Organic Chemistry II (acids, esters, carbonyl compounds, acid chlorides, nitrogen compounds, and further halogeno-compounds, Topic 5.3 Organic chemistry III (reaction mechanisms and aromatic compounds)[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]Nuffield Chemistry:[/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] 8086/9086 Unit 1 Introductory Chemistry Topic 2 Alcohols: an introduction to organic chemistry, Unit 2 Bonding and reactions: Topic 8 Organic Chemistry: Hydrocarbons, Topic 10 Halogenoalkanes (haloalkanes), Unit 4 Energy and reactions: Topic 12 Arenes: benzene and phenol[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]AQA Chemistry:[/SIZE][/FONT][/B] [FONT=Comic Sans MS][SIZE=2] 5421/6421 Module 3 Introduction to Organic Chemistry/Practical: Chlorination alkanes, alkene reactions, haloalkanes, alcohols; Module 4 Further Physical and Organic Chemistry: aldehydes and ketones reactions, carboxylic acids and esters, acylation, aromatic chemistry, amines[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] International Baccalaureate Chemistry[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: Topic 16 Kinetics: 16.2 Reaction Mechanism; Topic 20 Organic Chemistry: 20.2 Hydrocarbons, 20.3 Nucleophilic substitution reactions, 20.4 Alcohols; Option A Higher Physical Organic Chemistry A.3 Reaction Mechanism, A.4 Nucleophilic substitution reactions; Option E Chemical Industries: Topic E.8 Mechanisms in the Organic Chemicals Industry; Option H Further Organic Chemistry: H.2 Free Radical Substitution Reactions, H.3 Electrophilic Addition Reactions, H.4 Electrophilic Substitution Reactions, H.5 Nucleophilic Addition Reactions, H.6 Nucleophilic Substitution Reactions, H.7 Elimination Reactions, H.8 Addition-elimination Reactions.[/SIZE][/FONT][/LEFT] [/LIST] [IMG]http://books.google.com/images/cleardot.gif[/IMG] [LIST] [*][/LIST] [/QUOTE]
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