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  1. <?xml version="1.0"?>
  2.  
  3. <chapter id="ch05" num="5" page="" xml:base="media/content/">
  4. <head>Organic View</head>
  5. <title>Stereochemistry: Chiral Molecules</title>
  6.  
  7. <section id="ch05_02" num="5.2" page="">
  8.     <title>Isomerism: Constitutional Isomers and Stereoisomers</title>
  9.  
  10.     <item id="ch05_02_01" type="3D" page="185">
  11.         <title>Butane</title>
  12.         <description>A 3D molecular model.</description>
  13.         <pdb src="ch05/3d/anti1but.pdb"/>
  14.     </item>
  15.  
  16.     <item id="ch05_02_02" type="3D" page="185">
  17.         <title>Isobutane</title>
  18.         <description>A 3D molecular model.</description>
  19.         <pdb src="ch05/3d/isobut.pdb"/>
  20.     </item>
  21.  
  22.     <item id="ch05_02_03" type="3D" page="185">
  23.         <title>1-Chloropropane</title>
  24.         <description>A 3D molecular model.</description>
  25.         <pdb src="ch05/3d/propyl.pdb"/>
  26.     </item>
  27.  
  28.     <item id="ch05_02_04" type="3D" page="185">
  29.         <title>2-Chloropropane</title>
  30.         <description>A 3D molecular model.</description>
  31.         <pdb src="ch05/3d/isoprop.pdb"/>
  32.     </item>
  33.  
  34.     <item id="ch05_02_05" type="3D" page="185">
  35.         <title>Ethanol</title>
  36.         <description>A 3D molecular model.</description>
  37.         <pdb src="ch05/3d/ethanol.PDB"/>
  38.     </item>
  39.  
  40.     <item id="ch05_02_06" type="3D" page="185">
  41.         <title>Dimethyl ether</title>
  42.         <description>A 3D molecular model.</description>
  43.         <pdb src="ch05/3d/MeOMe.pdb"/>
  44.     </item>
  45.  
  46.     <item id="ch05_02_07" type="3D" page="185">
  47.         <title>cis -1,2-Dichloroethene</title>
  48.         <description>A 3D molecular model.</description>
  49.         <pdb src="ch05/3d/c12dicl.pdb"/>
  50.     </item>
  51.  
  52.     <item id="ch05_02_08" type="3D" page="185">
  53.         <title>trans -1,2-Dichloroethene</title>
  54.         <description>A 3D molecular model.</description>
  55.         <pdb src="ch05/3d/t12dicl.pdb"/>
  56.     </item>
  57.  
  58.     <item id="ch05_02_09" type="3D" page="186">
  59.         <title>cis and trans-1,2-dimethylcyclopentane</title>
  60.         <description>A 3D molecular model.</description>
  61.         <pdb src="ch05/3d/C512dm.pdb"/>
  62.     </item>
  63.  
  64.     <item id="ch05_02_10" type="3D" page="193">
  65.         <title>D-Alanine</title>
  66.         <description></description>
  67.         <c3d src="ch05/c3d/D-alanine.C3D"/>
  68.     </item>
  69.  
  70.     <item id="ch05_02_11" type="3D" page="193">
  71.         <title>L-Alanine</title>
  72.         <description></description>
  73.         <c3d src="ch05/c3d/L-alanine.C3D"/>
  74.     </item>
  75.  
  76.  
  77. </section>
  78.  
  79. <section id="ch05_03" num="5.3" page="">
  80.     <title>Enantiomers and Chiral Molecules</title>
  81.  
  82.     <item id="ch05_03_01" type="3D" page="188">
  83.         <title>structure I, (R)-2-butanol</title>
  84.         <description>A 3D molecular model.</description>
  85.         <pdb src="ch05/3d/(R)BUT.PDB"/>
  86.     </item>
  87.  
  88.     <item id="ch05_03_02" type="3D" page="188">
  89.         <title>structure II, (S)-2-butanol</title>
  90.         <description>A 3D molecular model.</description>
  91.         <pdb src="ch05/3d/(S)BUT.PDB"/>
  92.     </item>
  93.  
  94.     <item id="ch05_03_03" type="CU" page="190">
  95.         <title>Tetrahedral Stereocenter</title>
  96.         <description>A graphics/audio presentation on a topic involving complex 3D structure or relationships or a dynamic process.</description>
  97.         <director src="ch05/cu/TetrCntr/dswmedia/TETRHD.dcr" width="640" height="480" border="0" id="TETRHD">
  98.             <param name="sw1" value="ch01_03_04"/>
  99.         </director>
  100.     </item>
  101.  
  102.     <item id="ch05_03_04" type="IE" page="190">
  103.         <title>Tetrahedral Stereocenter</title>
  104.         <description></description>
  105.         <director src="ch05/ie/iTetCtr/dswmedia/iTetCtr.dcr" width="640" height="480" border="0"/>
  106.     </item>
  107. <!--
  108.     <item id="ch05_03_05" type="IE" page="191">
  109.         <title>Comparing Enantiomers</title>
  110.         <description></description>
  111.         <director src="" width="640" height="480" border="0"/>
  112.     </item>
  113. -->
  114.     <item id="ch05_03_06" type="3D" page="191">
  115.         <title>2-propanol</title>
  116.         <description>A 3D molecular model.</description>
  117.         <pdb src="ch05/3d/iPrOH.pdb"/>
  118.     </item>
  119.  
  120.     <item id="ch05_03_07" type="CU" page="191">
  121.         <title>Two Identical Groups (Three Different Groups)</title>
  122.         <description>A graphics/audio presentation on a topic involving complex 3D structure or relationships or a dynamic process.</description>
  123.         <director src="ch05/cu/ThreeGrp/dswmedia/THREEG.dcr" width="640" height="480" border="0" id="THREEG">
  124.             <param name="sw1" value="ch05_03_08"/>
  125.         </director>
  126.     </item>
  127.  
  128.     <item id="ch05_03_08" type="IE" page="191">
  129.         <title>Two Identical Groups (Three Different Groups)</title>
  130.         <description></description>
  131.         <director src="ch05/ie/i3grps/dswmedia/i3grps.dcr" width="640" height="480" border="0"/>
  132.     </item>
  133. <!--
  134.     <item id="ch05_03_09" type="IE" page="191">
  135.         <title>Models with three Different Groups</title>
  136.         <description></description>
  137.         <director src="" width="640" height="480" border="0"/>
  138.     </item>
  139. -->
  140.     <item id="ch05_03_10" type="3D" page="201">
  141.         <title>Thalidomide</title>
  142.         <description></description>
  143.         <c3d src="ch05/c3d/thalidomide.C3D"/>
  144.     </item>
  145.  
  146. </section>
  147.  
  148. <section id="ch05_04" num="5.4" page="">
  149.     <title>The Biological Importance of Chirality</title>
  150.  
  151.     <item id="ch05_04_01" type="3D" page="192">
  152.         <title>limonene</title>
  153.         <description>A 3D molecular model.</description>
  154.         <pdb src="ch05/3d/LIMONENE.PDB"/>
  155.     </item>
  156.  
  157.     <item id="ch05_04_02" type="3D" page="192">
  158.         <title>(+)-Carvone (from caraway)</title>
  159.         <description>A 3D molecular model.</description>
  160.         <pdb src="ch05/3d/carvoneP.pdb"/>
  161.     </item>
  162.  
  163.     <item id="ch05_04_03" type="3D" page="192">
  164.         <title>(-)-Carvone (from spearmint)</title>
  165.         <description>A 3D molecular model.</description>
  166.         <pdb src="ch05/3d/carvoneM.pdb"/>
  167.     </item>
  168.  
  169.     <item id="ch05_04_04" type="3D" page="193">
  170.         <title>Thalidoamide</title>
  171.         <description>A 3D molecular model.</description>
  172.         <pdb src="ch05/3d/THALDOMD.PDB"/>
  173.     </item>
  174.  
  175.     <item id="ch05_04_05" type="3D" page="201">
  176.         <title>R-Limonene</title>
  177.         <description></description>
  178.         <c3d src="ch05/c3d/R-limonene.C3D"/>
  179.     </item>
  180.  
  181.     <item id="ch05_04_06" type="3D" page="201">
  182.         <title>S-Limonene</title>
  183.         <description></description>
  184.         <c3d src="ch05/c3d/S-limonene.C3D"/>
  185.     </item>
  186.  
  187. </section>
  188.  
  189. <!--<section id="ch05_05" num="5.5" page="">
  190.     <title>The Historical Origin of Stereochemistry</title>
  191. </section>!-->
  192.  
  193. <section id="ch05_06" num="5.6" page="">
  194.     <title>Tests for Chirality: Planes of Symmetry</title>
  195.  
  196.     <item id="ch05_06_01" type="AG" page="194">
  197.         <title>Planes of symmetry in 2-chloropropane and 2-chlorobutane</title>
  198.         <description>A rotating, 3D version  of a text graphic.</description>
  199.         <director src="ch05/ag/Qplanes/dswmedia/Qplanes.dcr" width="640" height="480" border="0"/>
  200.     </item>
  201.  
  202.     <item id="ch05_06_02" type="3D" page="194">
  203.         <title>2-Chloropropane</title>
  204.         <description>A 3D molecular model.</description>
  205.         <pdb src="ch05/3d/isoprop.pdb"/>
  206.     </item>
  207.  
  208.     <item id="ch05_06_03" type="3D" page="194">
  209.         <title>2-Chlorobutane</title>
  210.         <description>A 3D molecular model.</description>
  211.         <pdb src="ch05/3d/sec-but.pdb"/>
  212.     </item>
  213. <!--
  214.     <item id="ch05_06_04" type="IE" page="194">
  215.         <title>Models with three Different Groups</title>
  216.         <description></description>
  217.         <director src="" width="640" height="480" border="0"/>
  218.     </item>
  219. -->
  220.  
  221.  
  222. </section>
  223.  
  224. <section id="ch05_07" num="5.7" page="">
  225.     <title>Nomenclature of Enantiomers: The (R-S) System</title>
  226.  
  227.     <item id="ch05_07_01" type="3D" page="195">
  228.         <title>structure I, (R)-2-butanol</title>
  229.         <description>A 3D molecular model.</description>
  230.         <pdb src="ch05/3d/(R)BUT.PDB"/>
  231.     </item>
  232.  
  233.     <item id="ch05_07_02" type="3D" page="195">
  234.         <title>structure II, (S)-2-butanol</title>
  235.         <description>A 3D molecular model.</description>
  236.         <pdb src="ch05/3d/(S)BUT.PDB"/>
  237.     </item>
  238.  
  239.     <item id="ch05_07_03" type="IE" page="196">
  240.         <title>R,S-Naming</title>
  241.         <description></description>
  242.         <director src="ch05/ie/iRSnmng/dswmedia/iRSnmng.dcr" width="640" height="480" border="0"/>
  243.     </item>
  244.  
  245.     <item id="ch05_07_04" type="CU" page="197">
  246.         <title>R,S-Naming</title>
  247.         <description>A graphics/audio presentation on a topic involving complex 3D structure or relationships or a dynamic process.</description>
  248.         <director src="ch05/cu/RSnaming/dswmedia/RSNAMING.dcr" width="640" height="480" border="0" id="RSNAMING">
  249.             <param name="sw1" value="ch05_07_05"/>
  250.         </director>
  251.     </item>
  252.  
  253.     <item id="ch05_07_05" type="IE" page="197">
  254.         <title>R,S-Naming</title>
  255.         <description></description>
  256.         <director src="ch05/ie/iRSnmng/dswmedia/iRSnmng.dcr" width="640" height="480" border="0"/>
  257.     </item>
  258. <!--
  259.     <item id="ch05_07_06" type="IE" page="198">
  260.         <title>R,S-Comparison, glyceraldehyde</title>
  261.         <description></description>
  262.         <director src="" width="640" height="480" border="0"/>
  263.     </item>
  264.  
  265.     <item id="ch05_07_07" type="IE" page="198">
  266.         <title>R,S-Comparisons</title>
  267.         <description></description>
  268.         <director src="" width="640" height="480" border="0"/>
  269.     </item>
  270.  
  271.     <item id="ch05_07_08" type="IE" page="199">
  272.         <title>Stereocenter Comparisons</title>
  273.         <description></description>
  274.         <director src="" width="640" height="480" border="0"/>
  275.     </item>
  276. -->
  277. </section>
  278.  
  279. <section id="ch05_08" num="5.8" page="">
  280.     <title>Properties of Enantiometers: Optical Activity</title>
  281.  
  282.     <item id="ch05_08_01" type="AG" page="201">
  283.         <title>Unpolarized Light and Plane-Polarized light</title>
  284.         <description>A rotating, 3D version  of a text graphic.</description>
  285.         <director src="ch05/ag/Qarrows/dswmedia/Qarrows.dcr" width="640" height="480" border="0"/>
  286.     </item>
  287.  
  288.     <item id="ch05_08_02" type="3D" page="205">
  289.         <title>(+)-Carvone (from caraway)</title>
  290.         <description>A 3D molecular model.</description>
  291.         <pdb src="ch05/3d/carvoneP.pdb"/>
  292.     </item>
  293.  
  294.     <item id="ch05_08_03" type="3D" page="205">
  295.         <title>(-)-Carvone (from spearmint)</title>
  296.         <description>A 3D molecular model.</description>
  297.         <pdb src="ch05/3d/carvoneM.pdb"/>
  298.     </item>
  299.  
  300. </section>
  301.  
  302. <!--<section id="ch05_09" num="5.9" page="">
  303.     <title>The Origin of optical Activity</title>
  304. </section>!-->
  305.  
  306. <section id="ch05_10" num="5.10" page="">
  307.     <title>The Synthesis of Chiral molecules</title>
  308.  
  309.     <item id="ch05_10_01" type="3D" page="209">
  310.         <title>(R)-2-butanol</title>
  311.         <description>A 3D molecular model.</description>
  312.         <pdb src="ch05/3d/(R)BUT.PDB"/>
  313.     </item>
  314.  
  315.     <item id="ch05_10_02" type="3D" page="209">
  316.         <title>(S)-2-butanol</title>
  317.         <description>A 3D molecular model.</description>
  318.         <pdb src="ch05/3d/(S)BUT.PDB"/>
  319.     </item>
  320.  
  321. </section>
  322.  
  323. <section id="ch05_11" num="5.11" page="">
  324.     <title>Chiral Drugs</title>
  325.  
  326.     <item id="ch05_11_01" type="3D" page="210">
  327.         <title>(S)-Ibuprofen</title>
  328.         <description>A 3D molecular model.</description>
  329.         <pdb src="ch05/3d/(S)IBUP.PDB"/>
  330.     </item>
  331.  
  332.     <item id="ch05_11_02" type="3D" page="210">
  333.         <title>(S)-Methyldopa</title>
  334.         <description>A 3D molecular model.</description>
  335.         <pdb src="ch05/3d/(s)mdop.pdb"/>
  336.     </item>
  337.  
  338.     <item id="ch05_11_03" type="3D" page="210">
  339.         <title>(S)-Penicillamine</title>
  340.         <description>A 3D molecular model.</description>
  341.         <pdb src="ch05/3d/(S)PENI.PDB"/>
  342.     </item>
  343.  
  344.     <item id="ch05_11_04" type="3D" page="218">
  345.         <title>(S)-Naproxen</title>
  346.         <description></description>
  347.         <c3d src="ch05/c3d/S-naproxen.C3D"/>
  348.     </item>
  349.  
  350. </section>
  351.  
  352. <section id="ch05_12" num="5.12" page="">
  353.     <title>Molecules with More Than One Stereocenter</title>
  354.  
  355.     <item id="ch05_12_01" type="3D" page="211">
  356.         <title>2,3-Dibromopentane, Stereoisomer 1</title>
  357.         <description>A 3D molecular model.</description>
  358.         <pdb src="ch05/3d/L1P23.PDB"/>
  359.     </item>
  360.  
  361.     <item id="ch05_12_02" type="3D" page="211">
  362.         <title>2,3-Dibromopentane, Stereoisomer 2</title>
  363.         <description>A 3D molecular model.</description>
  364.         <pdb src="ch05/3d/R2P23.PDB"/>
  365.     </item>
  366.  
  367.     <item id="ch05_12_03" type="3D" page="212">
  368.         <title>2,3-Dibromopentane, Stereoisomer 3</title>
  369.         <description>A 3D molecular model.</description>
  370.         <pdb src="ch05/3d/L3P23.PDB"/>
  371.     </item>
  372.  
  373.     <item id="ch05_12_04" type="3D" page="212">
  374.         <title>2,3-Dibromopentane, Stereoisomer 4</title>
  375.         <description>A 3D molecular model.</description>
  376.         <pdb src="ch05/3d/R4P23.PDB"/>
  377.     </item>
  378.  
  379.     <item id="ch05_12_05" type="3D" page="212">
  380.         <title>2,3-Dibromopentane, Stereoisomers montage</title>
  381.         <description>A 3D molecular model.</description>
  382.         <pdb src="ch05/3d/P23MNT.PDB"/>
  383.     </item>
  384. <!--
  385.     <item id="ch05_12_06" type="IE" page="212">
  386.         <title>Dibromopentane, Stereoisomers</title>
  387.         <description></description>
  388.         <director src="" width="640" height="480" border="0"/>
  389.     </item>
  390. -->
  391.     <item id="ch05_12_07" type="3D" page="213">
  392.         <title>2,3-Dibromobutane, Stereoisomer A</title>
  393.         <description>A 3D molecular model.</description>
  394.         <pdb src="ch05/3d/LAB23.PDB"/>
  395.     </item>
  396.  
  397.     <item id="ch05_12_08" type="3D" page="213">
  398.         <title>2,3-Dibromobutane, Stereoisomer B</title>
  399.         <description>A 3D molecular model.</description>
  400.         <pdb src="ch05/3d/RBB23.PDB"/>
  401.     </item>
  402.  
  403.     <item id="ch05_12_09" type="3D" page="213">
  404.         <title>2,3-Dibromobutane, Stereoisomer C</title>
  405.         <description>A 3D molecular model.</description>
  406.         <pdb src="ch05/3d/LCB23.PDB"/>
  407.     </item>
  408.  
  409.     <item id="ch05_12_10" type="3D" page="213">
  410.         <title>2,3-Dibromobutane, Stereoisomer D</title>
  411.         <description>A 3D molecular model.</description>
  412.         <pdb src="ch05/3d/RDB23.PDB"/>
  413.     </item>
  414. <!--
  415.     <item id="ch05_12_11" type="IE" page="212">
  416.         <title>Dibromobutane, Stereoisomers</title>
  417.         <description></description>
  418.         <director src="" width="640" height="480" border="0"/>
  419.     </item>
  420. -->
  421.     <item id="ch05_12_12" type="3D" page="214">
  422.         <title>2,3-Dibromobutane</title>
  423.         <description>A 3D molecular model.</description>
  424.         <pdb src="ch05/3d/LAB23.PDB"/>
  425.     </item>
  426.  
  427.     <item id="ch05_12_13" type="3D" page="215">
  428.         <title>Chloramphenicol</title>
  429.         <description>A 3D molecular model.</description>
  430.         <pdb src="ch05/3d/CLAMPH.PDB"/>
  431.     </item>
  432.  
  433. </section>
  434.  
  435. <section id="ch05_13" num="5.13" page="">
  436.     <title>Fischer Projection Formulas</title>
  437.  
  438.     <item id="ch05_13_01" type="3D" page="216">
  439.         <title>2,3-Dibromobutane, Stereoisomer A</title>
  440.         <description>A 3D molecular model.</description>
  441.         <pdb src="ch05/3d/LAB23.PDB"/>
  442.     </item>
  443.  
  444.     <item id="ch05_13_02" type="3D" page="216">
  445.         <title>2,3-Dibromobutane, Stereoisomer B</title>
  446.         <description>A 3D molecular model.</description>
  447.         <pdb src="ch05/3d/RBB23.PDB"/>
  448.     </item>
  449.  
  450. </section>
  451.  
  452. <section id="ch05_14" num="5.14" page="">
  453.     <title>Stereoisomerism of Cyclic Compounds</title>
  454.  
  455.     <item id="ch05_14_01" type="3D" page="217">
  456.         <title>1,2-Dimethylcyclopentane, Stereoisomer 5</title>
  457.         <description>A 3D molecular model.</description>
  458.         <pdb src="ch05/3d/R5T12DM.PDB"/>
  459.     </item>
  460.  
  461.     <item id="ch05_14_02" type="3D" page="217">
  462.         <title>1,2-Dimethylcyclopentane, Stereoisomer 6</title>
  463.         <description>A 3D molecular model.</description>
  464.         <pdb src="ch05/3d/L5T12DM.PDB"/>
  465.     </item>
  466.  
  467.     <item id="ch05_14_03" type="3D" page="217">
  468.         <title>1,2-Dimethylcyclopentane, Stereoisomer 7</title>
  469.         <description>A 3D molecular model.</description>
  470.         <pdb src="ch05/3d/M512DM.PDB"/>
  471.     </item>
  472. <!--
  473.     <item id="ch05_14_04" type="IE" page="217">
  474.         <title>1,3-Dimethylcyclopentane Stereoisomers</title>
  475.         <description></description>
  476.         <director src="" width="640" height="480" border="0"/>
  477.     </item>
  478. -->
  479.     <item id="ch05_14_05" type="3D" page="218">
  480.         <title>cis -1,4-Dimethylcyclohexane</title>
  481.         <description>A 3D molecular model.</description>
  482.         <pdb src="ch05/3d/c14dma.pdb"/>
  483.     </item>
  484. <!--
  485.     <item id="ch05_14_06" type="IE" page="218">
  486.         <title>cis -1,4-Dimethylcyclohexane</title>
  487.         <description></description>
  488.         <director src="" width="640" height="480" border="0"/>
  489.     </item>
  490. -->
  491.     <item id="ch05_14_07" type="3D" page="218">
  492.         <title>trans -1,4-Dimethylcyclohexane</title>
  493.         <description>A 3D molecular model.</description>
  494.         <pdb src="ch05/3d/14DEDM.PDB"/>
  495.     </item>
  496. <!--
  497.     <item id="ch05_14_08" type="IE" page="218">
  498.         <title>trans -1,4-Dimethylcyclohexane</title>
  499.         <description></description>
  500.         <director src="" width="640" height="480" border="0"/>
  501.     </item>
  502. -->
  503.     <item id="ch05_14_09" type="3D" page="218">
  504.         <title>cis -1,3-Dimethylcyclohexane</title>
  505.         <description>A 3D molecular model.</description>
  506.         <pdb src="ch05/3d/ce13dm.pdb"/>
  507.     </item>
  508. <!--
  509.     <item id="ch05_14_10" type="IE" page="218">
  510.         <title>cis -1,3-Dimethylcyclohexane</title>
  511.         <description></description>
  512.         <director src="" width="640" height="480" border="0"/>
  513.     </item>
  514. -->
  515.     <item id="ch05_14_11" type="3D" page="218">
  516.         <title>trans -1,3-Dimethylcyclohexane (a)</title>
  517.         <description>A 3D molecular model.</description>
  518.         <pdb src="ch05/3d/lat13dm.pdb"/>
  519.     </item>
  520. <!--
  521.     <item id="ch05_14_12" type="IE" page="218">
  522.         <title>trans -1,3-Dimethylcyclohexane</title>
  523.         <description></description>
  524.         <director src="" width="640" height="480" border="0"/>
  525.     </item>
  526. -->
  527.     <item id="ch05_14_13" type="3D" page="218">
  528.         <title>trans -1,3-Dimethylcyclohexane (b)</title>
  529.         <description>A 3D molecular model.</description>
  530.         <pdb src="ch05/3d/rat13dm.pdb"/>
  531.     </item>
  532. <!--
  533.     <item id="ch05_14_14" type="IE" page="218">
  534.         <title>trans -1,3-Dimethylcyclohexane</title>
  535.         <description></description>
  536.         <director src="" width="640" height="480" border="0"/>
  537.     </item>
  538. -->
  539.     <item id="ch05_14_15" type="3D" page="219">
  540.         <title>trans -1,2-Dimethylcyclohexane (a)</title>
  541.         <description>A 3D molecular model.</description>
  542.         <pdb src="ch05/3d/lt12dm.pdb"/>
  543.     </item>
  544.  
  545.     <item id="ch05_14_16" type="3D" page="219">
  546.         <title>trans -1,2-Dimethylcyclohexane (b)</title>
  547.         <description>A 3D molecular model.</description>
  548.         <pdb src="ch05/3d/rt12dm.pdb"/>
  549.     </item>
  550. <!--
  551.     <item id="ch05_14_17" type="IE" page="219">
  552.         <title>trans -1,2-Dimethylcyclohexane</title>
  553.         <description></description>
  554.         <director src="" width="640" height="480" border="0"/>
  555.     </item>
  556. -->
  557.     <item id="ch05_14_18" type="3D" page="219">
  558.         <title>cis -1,2-Dimethylcyclohexane (a)</title>
  559.         <description>A 3D molecular model.</description>
  560.         <pdb src="ch05/3d/cl12dm.pdb"/>
  561.     </item>
  562.  
  563.     <item id="ch05_14_19" type="3D" page="219">
  564.         <title>cis -1,2-Dimethylcyclohexane (b)</title>
  565.         <description>A 3D molecular model.</description>
  566.         <pdb src="ch05/3d/cr12dm.pdb"/>
  567.     </item>
  568. <!--
  569.     <item id="ch05_14_20" type="IE" page="219">
  570.         <title>cis -1,2-Dimethylcyclohexane</title>
  571.         <description></description>
  572.         <director src="" width="640" height="480" border="0"/>
  573.     </item>
  574. -->
  575. </section>
  576.  
  577. <section id="ch05_15" num="5.15" page="">
  578.     <title>Relating Configurations Through Reactions in Which No Bonds to the Stereocenter Are Broken</title>
  579.  
  580.     <item id="ch05_15_01" type="3D" page="220">
  581.         <title>(S)-(-)-2-Methyl-1-butanol</title>
  582.         <description>A 3D molecular model.</description>
  583.         <pdb src="ch05/3d/mebu214.pdb"/>
  584.     </item>
  585.  
  586.     <item id="ch05_15_02" type="3D" page="220">
  587.         <title>(S)-(+)-1-Chloro-2-methylbutane</title>
  588.         <description>A 3D molecular model.</description>
  589.         <pdb src="ch05/3d/clbu214.pdb"/>
  590.     </item>
  591.  
  592.     <item id="ch05_15_03" type="3D" page="220">
  593.         <title>(R)-1-Bromo-2-butanol</title>
  594.         <description>A 3D molecular model.</description>
  595.         <pdb src="ch05/3d/brbu215.pdb"/>
  596.     </item>
  597.  
  598.     <item id="ch05_15_04" type="3D" page="220">
  599.         <title>(S)- 2-Butanol</title>
  600.         <description>A 3D molecular model.</description>
  601.         <pdb src="ch05/3d/(S)BUT.PDB"/>
  602.     </item>
  603.  
  604.     <item id="ch05_15_05" type="3D" page="221">
  605.         <title>(R)-(+)-Glyceraldehyde (D-Glyceraldehyde)</title>
  606.         <description>A 3D molecular model.</description>
  607.         <pdb src="ch05/3d/(R)GLYC.PDB"/>
  608.     </item>
  609.  
  610.     <item id="ch05_15_06" type="3D" page="221">
  611.         <title>(S)-(-)-Glyceraldehyde (L-Glyceraldehyde)</title>
  612.         <description>A 3D molecular model.</description>
  613.         <pdb src="ch05/3d/(S)GLYC.PDB"/>
  614.     </item>
  615.  
  616.     <item id="ch05_15_07" type="3D" page="221">
  617.         <title>(R)-(-)-Lactic Acid</title>
  618.         <description>A 3D molecular model.</description>
  619.         <pdb src="ch05/3d/lactic.pdb"/>
  620.     </item>
  621.  
  622.     <item id="ch05_15_08" type="3D" page="222">
  623.         <title>(+)-Tartaric Acid</title>
  624.         <description>A 3D molecular model.</description>
  625.         <pdb src="ch05/3d/tartaric.pdb"/>
  626.     </item>
  627.  
  628. </section>
  629.  
  630. <!--<section id="ch05_16" num="5.16" page="">
  631.     <title>Separation of Entantiomers: Resolution</title>
  632. </section>
  633.  
  634. <section id="ch05_17" num="5.17" page="">
  635.     <title>Compounds with Stereocenters Other than Carbon</title>
  636. </section>!-->
  637.  
  638. <section id="ch05_18" num="5.18" page="">
  639.     <title>Chiral Molecules That Do Not Possess a Tetrahedral Atom with Four Different Groups</title>
  640.  
  641.     <item id="ch05_18_01" type="AG" page="224">
  642.         <title>Allene Orbitals</title>
  643.         <description>A graphics/audio presentation on a topic involving complex 3D structure or relationships or a dynamic process.</description>
  644.         <director src="ch05/ag/Qallene/dswmedia/Qallene.dcr" width="640" height="480" border="0"/>
  645.     </item>
  646.  
  647.     <item id="ch05_18_02" type="3D" page="224">
  648.         <title>1,3-Dichloroallene (left)</title>
  649.         <description>A 3D molecular model.</description>
  650.         <pdb src="ch05/3d/all219l.pdb"/>
  651.     </item>
  652.  
  653.     <item id="ch05_18_03" type="3D" page="224">
  654.         <title>1,3-Dichloroallene (right)</title>
  655.         <description>A 3D molecular model.</description>
  656.         <pdb src="ch05/3d/all219r.pdb"/>
  657.     </item>
  658.  
  659.     <item id="ch05_18_04" type="3D" page="232">
  660.         <title>(S)-BINAP</title>
  661.         <description></description>
  662.         <c3d src="ch05/c3d/S-BINAP.C3D"/>
  663.     </item>
  664.  
  665.     <item id="ch05_18_05" type="3D" page="232">
  666.         <title>(R)-BINAP</title>
  667.         <description></description>
  668.         <c3d src="ch05/c3d/R-BINAP.C3D"/>
  669.     </item>
  670.  
  671. </section>
  672.  
  673. </chapter>