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<blockquote data-quote="MaD-DoC" data-source="post: 1304549" data-attributes="member: 56284"><p style="text-align: center"><strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 15px"> IMPORTANT DEFINITIONS and ORGANIC TERMINOLOGY</span></span></strong></p><p> <p style="text-align: center"> <strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 12px">An alphabetical list of some terms used in organic reactions</span></span></strong></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">abstraction</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: When one reacting species removes an atom/ion from another molecule, radical or ion. </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. a methyl radical abstracts a chlorine atom from a chlorine 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"><strong>CH3. + Cl2 </strong>==><strong> CH3Cl + .Cl</strong> (see <strong>mechanisms Part Ia</strong>)</span></span> </p> </li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">or a water molecule abstracting a proton from a protonated alcohol 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"><strong>H2O + CH3CH2OH2+ </strong> ==><strong> H3O+ + CH3CH2OH</strong> (see <strong> mechanisms Part III</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">Though the phrase <strong>proton transfer</strong> is more appropriate here.</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">acylation</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: The introduction of a <strong>R-C=O</strong> group into a molecule (R = alkyl or aryl). (see <strong> mechanisms Part IV</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">acylonium ion</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: A type of carbocation formed in the electrophilic substitution alkylation of aromatic compounds </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. <strong> CH3-C+=O</strong> or <strong>CH3CO+</strong> where the positive charge is carried on the carbon of the <strong>C</strong>=O bond. They are formed e.g. in the aluminium chloride catalysed acylation of aromatic compounds. (see <strong> mechanisms Part IV</strong>)</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"> activated</span></span><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> complex</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: An unstable or 'transient state' formed when two reactant particles collide with sufficient kinetic energy in a reaction mechanism step. The activated complex breaks down to give the products. (see <strong> mechanisms Part II</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">activation energy Ea</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: The minimum energy reacting particles must possess in order to form an 'activated complex' or transition state before forming the products. Its the top of the hump on a reaction progress energy profile diagram. (see <strong> mechanisms Part II</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">addition</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">: The adding of one molecule to another with no other product, but not necessarily in a single reaction step. </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">The molecule is often added in two parts across e.g. a double bond </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. <strong> electrophilic</strong> addition of hydrogen halide to alkenes: </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">><strong>C=C<</strong> + <strong>HX </strong> ==> ><strong>CH-CX</strong>< (see <strong> mechanisms Part Ib</strong>)</span></span> </p> </li> </ul></li> <li data-xf-list-type="ul"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">or <strong> nucleophilic</strong> addition of hydrogen cyanide to aldehydes/ketones </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">><strong>C=O</strong> + <strong>HCN </strong>==><strong> >C(OH)-CN</strong> (see <strong> mechanisms Part III</strong>)</span></span> </p> </li> </ul></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">alkoxy </span></span> </strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> group: An alkyl-oxygen part of a molecule e.g. <strong>CH3CH2-O</strong>- is an ethoxy group. </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">alkyl </span></span> </strong> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> group: A saturated section of a molecule derived from an alkane 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">-<strong>CH3 methyl</strong>, -<strong>CH2CH3 ethyl</strong>, or -<strong>CH2CH2CH3 propyl</strong> etc.</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">arrows</span></span></strong><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">, <strong> use of in mechanisms</strong>: A <strong> half-arrow head means a single electron shift</strong> and a <strong> full arrow head shows an electron pair shift</strong> and used in the context of <strong>making or breaking bonds</strong>. Examples: 1. to 2. show single electron shifts and 4. to 6. show bond pair shifts. </span></span> </p> <ol> <li data-xf-list-type="ol"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"><img src="http://www.docbrown.info/page15/arrowuse1.gif" alt="" class="fr-fic fr-dii fr-draggable " style="" /> </span> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px">The bonding pair of electrons of the chlorine molecule is split between the two chlorine atoms/radicals on homolytic bond fission in the initiation of a free radical chain reaction. (for 1. and 2. see <strong> mechanisms Part Ia</strong>)</span></span> </span> </p> </li> <li data-xf-list-type="ol"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"><img src="http://www.docbrown.info/page15/arrowuse2.gif" alt="" class="fr-fic fr-dii fr-draggable " style="" /> One electron from each radical pairs up to form a C-Cl covalent bond in a free radical chain termination step. </span></span> </p> </li> <li data-xf-list-type="ol"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"><img src="http://www.docbrown.info/page15/arrowuse3.gif" alt="" class="fr-fic fr-dii fr-draggable " style="" /> A bond pair from the alkene is donated to a proton on the oxonium ion, H3O+, forming a C-H bond and simultaneously the H-O bond pair moves completely on to the oxygen to form a lone pair of non-bonding electrons. (see <strong>mechanisms Part Ib</strong>) </span></span> </p> </li> <li data-xf-list-type="ol"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"><img src="http://www.docbrown.info/page15/arrowuse4.gif" alt="" class="fr-fic fr-dii fr-draggable " style="" /> A hydroxide ion, OH-, donates a lone pair of non-bonding electrons to a carbon atom to form a C-OH bond and simultaneously the C-Cl bond pair shifts to become a lone pair of electrons on the chlorine atom as a chloride ion is formed. (see <strong>mechanisms Part II</strong>) </span></span> </p> </li> <li data-xf-list-type="ol"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"><img src="http://www.docbrown.info/page15/arrowuse5.gif" alt="" class="fr-fic fr-dii fr-draggable " style="" /> The cyanide ion, -CN, donates a lone pair of electrons to form a C-N bond and simultaneously one of the C=O bond pairs moves completely on to the oxygen to form a lone pair of non-bonding electrons and giving the oxygen atom an overall single positive charge. (see <strong> mechanisms Part III</strong>) </span></span> </p> </li> <li data-xf-list-type="ol"> <p style="text-align: left"><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"><img src="http://www.docbrown.info/page15/arrowuse6.gif" alt="" class="fr-fic fr-dii fr-draggable " style="" /> The C-H bond pair shifts to complete the </span></span> <span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> ∏ </span></span><span style="font-family: 'Comic Sans MS'"><span style="font-size: 10px"> electrons of the benzene ring and simultaneously a hydrogensulphate ion donates a lone pair and forms an H-O bond in forming a sulphuric acid molecule. (see <strong> mechanisms Part IV</strong>) </span></span> </p> </li> </ol></li> </ul></blockquote><p></p>
[QUOTE="MaD-DoC, post: 1304549, member: 56284"] [CENTER][B][FONT=Comic Sans MS][SIZE=4] IMPORTANT DEFINITIONS and ORGANIC TERMINOLOGY[/SIZE][/FONT][/B][/CENTER] [CENTER] [B][FONT=Comic Sans MS][SIZE=3]An alphabetical list of some terms used in organic reactions[/SIZE][/FONT][/B][/CENTER] [LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]abstraction[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: When one reacting species removes an atom/ion from another molecule, radical or ion. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]e.g. a methyl radical abstracts a chlorine atom from a chlorine molecule [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2][B]CH3. + Cl2 [/B]==>[B] CH3Cl + .Cl[/B] (see [B]mechanisms Part Ia[/B])[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]or a water molecule abstracting a proton from a protonated alcohol molecule [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2][B]H2O + CH3CH2OH2+ [/B] ==>[B] H3O+ + CH3CH2OH[/B] (see [B] mechanisms Part III[/B])[/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]Though the phrase [B]proton transfer[/B] is more appropriate here.[/SIZE][/FONT] [/LEFT] [/LIST] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]acylation[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: The introduction of a [B]R-C=O[/B] group into a molecule (R = alkyl or aryl). (see [B] mechanisms Part IV[/B])[/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]acylonium ion[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: A type of carbocation formed in the electrophilic substitution alkylation of aromatic compounds [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]e.g. [B] CH3-C+=O[/B] or [B]CH3CO+[/B] where the positive charge is carried on the carbon of the [B]C[/B]=O bond. They are formed e.g. in the aluminium chloride catalysed acylation of aromatic compounds. (see [B] mechanisms Part IV[/B])[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2] activated[/SIZE][/FONT][FONT=Comic Sans MS][SIZE=2] complex[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: An unstable or 'transient state' formed when two reactant particles collide with sufficient kinetic energy in a reaction mechanism step. The activated complex breaks down to give the products. (see [B] mechanisms Part II[/B])[/SIZE][/FONT] [/LEFT] [*][LEFT][B][FONT=Comic Sans MS][SIZE=2]activation energy Ea[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: The minimum energy reacting particles must possess in order to form an 'activated complex' or transition state before forming the products. Its the top of the hump on a reaction progress energy profile diagram. (see [B] mechanisms Part II[/B]) [/SIZE][/FONT] [/LEFT] [*][LEFT][B][FONT=Comic Sans MS][SIZE=2]addition[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2]: The adding of one molecule to another with no other product, but not necessarily in a single reaction step. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]The molecule is often added in two parts across e.g. a double bond [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]e.g. [B] electrophilic[/B] addition of hydrogen halide to alkenes: [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]>[B]C=C<[/B] + [B]HX [/B] ==> >[B]CH-CX[/B]< (see [B] mechanisms Part Ib[/B])[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]or [B] nucleophilic[/B] addition of hydrogen cyanide to aldehydes/ketones [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]>[B]C=O[/B] + [B]HCN [/B]==>[B] >C(OH)-CN[/B] (see [B] mechanisms Part III[/B])[/SIZE][/FONT] [/LEFT] [/LIST] [/LIST] [/LIST] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]alkoxy [/SIZE][/FONT] [/B] [FONT=Comic Sans MS][SIZE=2] group: An alkyl-oxygen part of a molecule e.g. [B]CH3CH2-O[/B]- is an ethoxy group. [/SIZE][/FONT] [/LEFT] [*] [LEFT][B][FONT=Comic Sans MS][SIZE=2]alkyl [/SIZE][/FONT] [/B] [FONT=Comic Sans MS][SIZE=2] group: A saturated section of a molecule derived from an alkane e.g. [/SIZE][/FONT] [/LEFT] [LIST] [*] [LEFT][FONT=Comic Sans MS][SIZE=2]-[B]CH3 methyl[/B], -[B]CH2CH3 ethyl[/B], or -[B]CH2CH2CH3 propyl[/B] etc.[/SIZE][/FONT] [/LEFT] [/LIST] [*] [LEFT] [B][FONT=Comic Sans MS][SIZE=2]arrows[/SIZE][/FONT][/B][FONT=Comic Sans MS][SIZE=2], [B] use of in mechanisms[/B]: A [B] half-arrow head means a single electron shift[/B] and a [B] full arrow head shows an electron pair shift[/B] and used in the context of [B]making or breaking bonds[/B]. Examples: 1. to 2. show single electron shifts and 4. to 6. show bond pair shifts. [/SIZE][/FONT] [/LEFT] [LIST=1] [*] [LEFT][FONT=Comic Sans MS][SIZE=2][IMG]http://www.docbrown.info/page15/arrowuse1.gif[/IMG] [/SIZE] [FONT=Comic Sans MS][SIZE=2]The bonding pair of electrons of the chlorine molecule is split between the two chlorine atoms/radicals on homolytic bond fission in the initiation of a free radical chain reaction. (for 1. and 2. see [B] mechanisms Part Ia[/B])[/SIZE][/FONT] [/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2][IMG]http://www.docbrown.info/page15/arrowuse2.gif[/IMG] One electron from each radical pairs up to form a C-Cl covalent bond in a free radical chain termination step. [/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2][IMG]http://www.docbrown.info/page15/arrowuse3.gif[/IMG] A bond pair from the alkene is donated to a proton on the oxonium ion, H3O+, forming a C-H bond and simultaneously the H-O bond pair moves completely on to the oxygen to form a lone pair of non-bonding electrons. (see [B]mechanisms Part Ib[/B]) [/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2][IMG]http://www.docbrown.info/page15/arrowuse4.gif[/IMG] A hydroxide ion, OH-, donates a lone pair of non-bonding electrons to a carbon atom to form a C-OH bond and simultaneously the C-Cl bond pair shifts to become a lone pair of electrons on the chlorine atom as a chloride ion is formed. (see [B]mechanisms Part II[/B]) [/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2][IMG]http://www.docbrown.info/page15/arrowuse5.gif[/IMG] The cyanide ion, -CN, donates a lone pair of electrons to form a C-N bond and simultaneously one of the C=O bond pairs moves completely on to the oxygen to form a lone pair of non-bonding electrons and giving the oxygen atom an overall single positive charge. (see [B] mechanisms Part III[/B]) [/SIZE][/FONT] [/LEFT] [*] [LEFT][FONT=Comic Sans MS][SIZE=2][IMG]http://www.docbrown.info/page15/arrowuse6.gif[/IMG] The C-H bond pair shifts to complete the [/SIZE][/FONT] [FONT=Comic Sans MS][SIZE=2] ∏ [/SIZE][/FONT][FONT=Comic Sans MS][SIZE=2] electrons of the benzene ring and simultaneously a hydrogensulphate ion donates a lone pair and forms an H-O bond in forming a sulphuric acid molecule. (see [B] mechanisms Part IV[/B]) [/SIZE][/FONT] [/LEFT] [/LIST] [/LIST] [/QUOTE]
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