Claisen Condensation | CHEMISTRY STUDY

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<span style="color: #af0000; font-family: Times; font-size: large;"><i>The Claisen Condensation</i></span></h2>
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<span style="font-family: Times;">The <b><i>nucleophilic </i></b>carbon of the enolate ion adds to the <b><i>electrophilic </i></b>carbon of a molecule of ethyl acetate that has not been deprotonated. A carbon-carbon bond is formed. The reaction produces yet another tetrahedral intemediate as shown in Equation 1.</span><br />
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<span style="font-family: Times;">Since the newly formed tetrahedral center has an electronegative atom attached to it, reformation of the carbonyl group, as shown in Equation 2, is a reasonable process.</span><br />
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<i><span style="font-size: large;"><b><span style="color: #0000af; font-family: Times;">         Exercise 1</span></b><span style="font-family: Times;"> </span></span></i></h4>
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<span style="font-family: Times;">Draw the structure of the major product you would expect to be formed in each of the following situations:</span></div>
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<b><span style="color: #0000af; font-family: Times; font-size: large;"><i>        Exercise 3:</i></span></b></h4>
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<span style="font-family: Times;">An <b><i>intramolecular </i></b>version of the <b><i><a href="http://forum-chemistry.blogspot.com/2014/08/claisen-condensationngung-tu-claisen.html" target="_blank">Claisen </a></i></b><i><b><a href="http://forum-chemistry.blogspot.com/2014/08/claisen-condensationngung-tu-claisen.html" target="_blank">condensation</a> </b></i>is known as the </span><span style="color: #af0000; font-family: Times;"><i><b>Dieckmann condensation</b></i></span><span style="font-family: Times;">. Equation 3 shows how this reaction was put to good use as part of the total synthesis of the prostaglandin </span><span style="font-family: Times;">PGA</span><sub><span style="font-family: Times;">2</span></sub><span style="font-family: Times;"><a href="https://www.blogger.com/null" name="PGA2"></a></span><span style="font-family: Times;">.</span><br />
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<span style="font-family: Times;">Equation 4 offers another example of the <b><i>Dieckmann condensation </i></b>that was involved in the synthesis of tropinone, a degradation product that was produced during the determination of the structure of the physiologically active alkaloid </span><span style="font-family: Times; font-style: normal; font-weight: normal;">atropine</span><span style="font-family: Times; font-style: normal; font-weight: normal;"><a href="https://www.blogger.com/null" name="Atropine"></a>.</span></div>
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<span style="font-family: Times; font-style: normal; font-weight: normal;">An early synthesis of </span><span style="font-family: Times; font-style: normal; font-weight: normal;">cholesterol</span><span style="font-family: Times;"><a href="https://www.blogger.com/null" name="Cholesterol"></a> involved the "mixed <b><i>Claisen </i></b><i><b>reaction</b></i>" shown if Equation 5.</span></div>
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<span style="font-family: Times;"><span style="font-size: large;"><i><span style="color: blue;">      Example 4</span></i><span style="color: black; font-style: normal; font-weight: normal;">  </span></span><span style="color: black; font-size: small; font-style: normal; font-weight: normal;">:</span></span><span style="background-color: white; color: black; font-family: 'PT Sans', arial, serif; font-size: small; letter-spacing: 1px; line-height: 28px;"><b><i>Dieckmann Condensation</i></b></span></h4>
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<i><span style="color: blue;">      <span style="font-size: large;">Example 5 </span></span></i>:<span style="background-color: white; font-family: 'PT Sans', arial, serif; font-size: small; letter-spacing: 1px; line-height: 28px;"><b><i>Crossed Claisen Condensation</i></b></span></h4>
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<span style="color: blue; font-size: large;"><i>     Example 6:</i></span></h4>
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<span style="background-color: white; color: #252525; font-family: sans-serif; font-size: 14px; line-height: 22.399999618530273px;">The classic </span><b style="background-color: white; color: #252525; font-family: sans-serif; font-size: 14px; line-height: 22.399999618530273px;"><i>Claisen condensation</i></b><span style="background-color: white; color: #252525; font-family: sans-serif; font-size: 14px; line-height: 22.399999618530273px;">, a self-condensation between two molecules of a compound containing an enolizable ester.</span></div>
<dl style="background-color: white; font-family: sans-serif; line-height: 22.399999618530273px; margin-bottom: 0.5em; margin-top: 0.2em;"><dd style="color: #252525; font-size: 14px; line-height: 1.6; margin-bottom: 0.1em; margin-left: 1.6em; margin-right: 0px;"><a class="image" href="http://en.wikipedia.org/wiki/File:Claisen_ethyl_acetate.png" style="background: none; color: #0b0080; text-decoration: none;"><img alt="Exercises about Claisen condensation" data-file-height="245" data-file-width="1200" height="80" src="http://upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Claisen_ethyl_acetate.png/350px-Claisen_ethyl_acetate.png" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Claisen_ethyl_acetate.png/525px-Claisen_ethyl_acetate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0b/Claisen_ethyl_acetate.png/700px-Claisen_ethyl_acetate.png 2x" style="border: none; vertical-align: middle;" title="Exercises about Claisen condensation" width="400" /></a></dd><dd style="line-height: 1.6; margin-bottom: 0.1em; margin-left: 1.6em; margin-right: 0px;"><h4 style="clear: both; font-family: 'Times New Roman'; line-height: normal;">
<span style="color: blue; font-size: large;">Example 7:</span></h4>
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<span style="color: #252525; font-family: sans-serif; font-size: 14px; line-height: 22.399999618530273px;">The mixed (or "crossed") Claisen condensation, where one enolizable ester or ketone and one nonenolizable ester are used.</span></div>
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<span style="color: blue; font-size: large;"><i>Example  8:</i></span></h4>
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The <b><i>Dieckmann condensation</i></b>, where a molecule with two ester groups reacts intramolecularly, forming a cyclic <b><i>β-keto ester</i></b>. In this case, the ring formed must not be strained, usually a 5- or 6-membered chain or ring.</div>
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<span style="color: blue; font-size: large;"><i>Example 9:</i></span></h4>
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The <b>Stobbe condensation</b> <sup class="reference" id="cite_ref-5" style="line-height: 1; unicode-bidi: -webkit-isolate;">[5]</sup> is a modification specific for the diethyl ester of succinic acid requiring less strong bases.<sup class="reference" id="cite_ref-6" style="line-height: 1; unicode-bidi: -webkit-isolate;">[6]</sup>An example is its reaction with benzophenone:<sup class="reference" id="cite_ref-7" style="line-height: 1; unicode-bidi: -webkit-isolate;">[7]</sup></div>
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<a class="image" href="http://en.wikipedia.org/wiki/File:StobbeCondensation.svg" style="background: none; color: #0b0080; text-decoration: none;" title="Stobbe condensation"><img alt="Stobbe condensation" data-file-height="93" data-file-width="683" height="93" src="http://upload.wikimedia.org/wikipedia/commons/thumb/f/ff/StobbeCondensation.svg/683px-StobbeCondensation.svg.png" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/ff/StobbeCondensation.svg/1025px-StobbeCondensation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/ff/StobbeCondensation.svg/1366px-StobbeCondensation.svg.png 2x" style="border: none; margin: 0px; vertical-align: middle;" width="683" /></a></div>
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A reaction mechanism that explains the formation of both an ester group and a carboxylic acid group is centered around alactone intermediate (<b>5</b>):</div>
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<a class="image" href="http://en.wikipedia.org/wiki/File:StobbeMechanism.svg" style="background: none; color: #0b0080;" title="Stobbe condensation mechanism"><img alt="Stobbe condensation mechanism" data-file-height="285" data-file-width="664" height="285" src="http://upload.wikimedia.org/wikipedia/commons/thumb/d/d4/StobbeMechanism.svg/664px-StobbeMechanism.svg.png" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/StobbeMechanism.svg/996px-StobbeMechanism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/StobbeMechanism.svg/1328px-StobbeMechanism.svg.png 2x" style="border: none; margin: 0px; vertical-align: middle;" title="Stobbe condensation mechanism" width="664" /></a></div>
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<span style="color: blue; font-size: large;"><i>Example 10:<a href="https://www.blogger.com/null" name="more"></a></i></span></h4>
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<span style="color: blue; font-size: large;"><i>Example 11:</i></span></h4>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgZtnYMYn2-3BSQgVacaIQwI4NO__TyGLTcU8c2SGSn_3qYSfHVOaCrSDuoX_4CSQbwtKb850cDEJS9VQxQAp7Hdfr2p0KtxONzOIKYhrwt6sFSbgh1RFnRab2LCqAIJK83FejixdVkeEs/s1600/dieckmann.gif" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img alt="Exercises about Claisen condensation" border="0" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgZtnYMYn2-3BSQgVacaIQwI4NO__TyGLTcU8c2SGSn_3qYSfHVOaCrSDuoX_4CSQbwtKb850cDEJS9VQxQAp7Hdfr2p0KtxONzOIKYhrwt6sFSbgh1RFnRab2LCqAIJK83FejixdVkeEs/s1600/dieckmann.gif" title="Exercises about Claisen condensation" /></a></div>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEi94WCp2v3QwPY0bURwvcG1v-TktpvLD58YwTW667rAmZmmw-5fWnSTYPFaedD0MYrWkqP6Xq3lMxYGwX6jcowq57p3LtmakC9y7J88DskbNj4u5qSVvBPo4JZ4cFcpcGQBReO3w5ouXAY/s1600/claisen05.gif" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img alt="Exercises about Claisen condensation" border="0" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEi94WCp2v3QwPY0bURwvcG1v-TktpvLD58YwTW667rAmZmmw-5fWnSTYPFaedD0MYrWkqP6Xq3lMxYGwX6jcowq57p3LtmakC9y7J88DskbNj4u5qSVvBPo4JZ4cFcpcGQBReO3w5ouXAY/s1600/claisen05.gif" title="Exercises about Claisen condensation" /></a>  </div>
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<span style="color: blue; font-size: large;"><i>Example 12:</i></span></h4>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjJ0KSgGIfSVnjShUsgcOrakQTa_WJpUiPYEKfRUEMJbs_G7P2lbeaMCjzkEFDYjzoSnnY2kj7kJmiOxqsFLnKtXlyaj2bUa3yiqY3ezVjvp9MTqY5b3eBlrQC7EKKOLHfIOlQcrykXrQY/s1600/11.jpg" imageanchor="1" style="line-height: 1.6; margin-left: 1em; margin-right: 1em;"><img alt="Exercises about Claisen condensation" border="0" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjJ0KSgGIfSVnjShUsgcOrakQTa_WJpUiPYEKfRUEMJbs_G7P2lbeaMCjzkEFDYjzoSnnY2kj7kJmiOxqsFLnKtXlyaj2bUa3yiqY3ezVjvp9MTqY5b3eBlrQC7EKKOLHfIOlQcrykXrQY/s1600/11.jpg" title="Exercises about Claisen condensation" /></a></div>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgtDk9N-x1a_p481MDxsd445gPCWNHA5ivZPH_fluouKPTxBXAXUxMzYz-AXN2W2qYrguk93W_ZAwQVWkGFG2N9ebKqi_1GqdMdl3KDMnulqD3TlH02bewjYJsTmXg0wTZZ7w63JjxLznc/s1600/12.jpg" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img alt="Exercises about Claisen condensation" border="0" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEgtDk9N-x1a_p481MDxsd445gPCWNHA5ivZPH_fluouKPTxBXAXUxMzYz-AXN2W2qYrguk93W_ZAwQVWkGFG2N9ebKqi_1GqdMdl3KDMnulqD3TlH02bewjYJsTmXg0wTZZ7w63JjxLznc/s1600/12.jpg" title="Exercises about Claisen condensation" /></a></div>
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<span style="color: blue; font-size: large;"><i>Example 13:</i></span></h4>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEihQ49WG09I6uCF7LnjQU_k2EhyGLm4uC1pS3VrQOGmnsLGXLWODhvFAblhracbtsgIdKiSfcFXoMQMxC8OqVaKCPSa-Xz-dPz4Dspx8h7u_F3xIQHSOEI9eZcADgbodYFA5NRx99aSWqY/s1600/ClaisenExample1.png" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img alt="Exercises about Claisen condensation" border="0" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEihQ49WG09I6uCF7LnjQU_k2EhyGLm4uC1pS3VrQOGmnsLGXLWODhvFAblhracbtsgIdKiSfcFXoMQMxC8OqVaKCPSa-Xz-dPz4Dspx8h7u_F3xIQHSOEI9eZcADgbodYFA5NRx99aSWqY/s1600/ClaisenExample1.png" title="Exercises about Claisen condensation" /></a></div>
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<span style="color: blue; font-size: large;"><i>Example 14:</i></span></h4>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjcJXS_XSb7L9GtiqA65enOkr6Q-x7yF33GUssyNzRSm9rlvaydprx5R9aimsjofYZbITspopuaFtr_m9dU-GJ3u2iBDF-KHENecikuNSbrnFu0EB6vPuW1sQLI-CyqPgtOyAO2EAYl5aE/s1600/dieckmann-condensation-reaction-mechanism.png" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img alt="Exercises about Claisen condensation" border="0" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjcJXS_XSb7L9GtiqA65enOkr6Q-x7yF33GUssyNzRSm9rlvaydprx5R9aimsjofYZbITspopuaFtr_m9dU-GJ3u2iBDF-KHENecikuNSbrnFu0EB6vPuW1sQLI-CyqPgtOyAO2EAYl5aE/s1600/dieckmann-condensation-reaction-mechanism.png" title="Exercises about Claisen condensation" /></a></div>
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<span style="color: blue; font-size: large;"><i>Example 15:</i></span></h4>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEhwwUrrLEus5PQ6sh2sgGiY03_8T5FQ1Q6Q4hUQlkZ7DmUrFPMSwQmlvO3vdeGqQcyvsf22keSHTEVjh0BpYV8C4vtVXFz5sleiLqV9rMh8WAxRx3Z0bzn5cGTVchR5ulAN5zJoGp-iFXk/s1600/dieckmann_condensation01.jpg" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img alt="Exercises about Claisen condensation" border="0" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEhwwUrrLEus5PQ6sh2sgGiY03_8T5FQ1Q6Q4hUQlkZ7DmUrFPMSwQmlvO3vdeGqQcyvsf22keSHTEVjh0BpYV8C4vtVXFz5sleiLqV9rMh8WAxRx3Z0bzn5cGTVchR5ulAN5zJoGp-iFXk/s1600/dieckmann_condensation01.jpg" title="Exercises about Claisen condensation" /></a>                                                                           </div>
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<span style="color: blue; font-size: large;">Example 16:</span></h4>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEigRmzzhxksoeaN6O6KP_txGiN0YMU_atc6Cb8S-_yg_s9h5Ih0w-LT1rsOrUGcXO7-Uw-27drOhHZX0WlBl-SdUpAwEKVnCz_YUFv1M44-qs6ypG9e2tR0XsOVjve27ed0lyj0t-hx8nA/s1600/DieckmannCondensationMechanism.png" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img alt="Exercises about Claisen condensation" border="0" height="139" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEigRmzzhxksoeaN6O6KP_txGiN0YMU_atc6Cb8S-_yg_s9h5Ih0w-LT1rsOrUGcXO7-Uw-27drOhHZX0WlBl-SdUpAwEKVnCz_YUFv1M44-qs6ypG9e2tR0XsOVjve27ed0lyj0t-hx8nA/s1600/DieckmannCondensationMechanism.png" title="Exercises about Claisen condensation" width="400" /></a></div>
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<span style="color: blue; font-size: large;"><i>Example 17:</i></span></h4>
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<a href="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjcumMQH3jTulkKWIRfyoUV5Mb0QPz-aOMuxVjQ6SiO66f9BhRro2K4XwzvbZYLg4GG-EclqrNNtjctxb6qA8LCzvFMJuZE0xUocqieIu2xhVbzmSlXiWG8DjxNqABzbRRzWXIDWYNrW6s/s1600/intramech.gif" imageanchor="1" style="margin-left: 1em; margin-right: 1em;"><img alt="Exercises about Claisen condensation" border="0" src="https://blogger.googleusercontent.com/img/b/R29vZ2xl/AVvXsEjcumMQH3jTulkKWIRfyoUV5Mb0QPz-aOMuxVjQ6SiO66f9BhRro2K4XwzvbZYLg4GG-EclqrNNtjctxb6qA8LCzvFMJuZE0xUocqieIu2xhVbzmSlXiWG8DjxNqABzbRRzWXIDWYNrW6s/s1600/intramech.gif" title="Exercises about Claisen condensation" /></a></div>
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<span style="color: blue; font-size: large;"><i>Example 18:</i></span></h4>
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Exercises about Claisen condensation

The Claisen Condensation The nucleophilic carbon of the enolate ion adds to the electrophilic carbon of a molecule of ethyl acetate that ...

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