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The Complete Mechanism of an Aldol Condensation
Although aldol condensation is one of the most important organic reactions, capable of forming new C–C bonds, its mechanism has never been fully established. We now conclude that the rate-limiting step in the base-catalyzed aldol condensation of benzaldehydes with acetophenones, to produce chalcones...
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Published in: | Journal of organic chemistry 2016-07, Vol.81 (13), p.5631-5635 |
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Language: | English |
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container_end_page | 5635 |
container_issue | 13 |
container_start_page | 5631 |
container_title | Journal of organic chemistry |
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creator | Perrin, Charles L Chang, Kuei-Lin |
description | Although aldol condensation is one of the most important organic reactions, capable of forming new C–C bonds, its mechanism has never been fully established. We now conclude that the rate-limiting step in the base-catalyzed aldol condensation of benzaldehydes with acetophenones, to produce chalcones, is the final loss of hydroxide and formation of the CC bond. This conclusion is based on a study of the partitioning ratios of the intermediate ketols and on the solvent kinetic isotope effects, whereby the condensations are faster in D2O than in H2O, regardless of substitution. |
doi_str_mv | 10.1021/acs.joc.6b00959 |
format | article |
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Org. Chem</addtitle><date>2016-07-01</date><risdate>2016</risdate><volume>81</volume><issue>13</issue><spage>5631</spage><epage>5635</epage><pages>5631-5635</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>Although aldol condensation is one of the most important organic reactions, capable of forming new C–C bonds, its mechanism has never been fully established. We now conclude that the rate-limiting step in the base-catalyzed aldol condensation of benzaldehydes with acetophenones, to produce chalcones, is the final loss of hydroxide and formation of the CC bond. 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title | The Complete Mechanism of an Aldol Condensation |
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