Aldol Condensation Reaction Rate Demonstrates Steric and Electronic Substituent Effects in the Organic Chemistry Lab

Autor:	Matthew D. Berardi, Isabelle Kozik, Filippo Gentile, Timothy M. Gregg
Rok vydání:	2021
Předmět:	Steric effects Reaction mechanism education Substituent General Chemistry Education Reaction rate chemistry.chemical_compound chemistry Aldol reaction Nucleophile Electrophile Organic chemistry Aldol condensation
Zdroj:	Journal of Chemical Education. 98:1732-1735
ISSN:	1938-1328 0021-9584
DOI:	10.1021/acs.jchemed.0c00448
Popis:	Aldol chemistry is highlighted in many introductory organic chemistry laboratory experiments because it provides synthesis, mechanism, and experimental challenges for students. In the experiment described here, students synthesize dibenzalacetone derivatives by crossed aldol condensation, observe reaction rates using a semiquantitative rubric, and illustrate the connection between reactant structures and reaction rate through their knowledge of the reaction mechanism. By combining class data and working through a guided-inquiry questionnaire, students link reaction rates with nucleophile and electrophile characteristics of the reactant structures. Independent rate determination of the aldol addition step, using UV absorption, confirmed that student rate observations of the overall reaction are a valid approach to learning about structure–function effects.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2b1c408b82a44a579c1c13cba2313fed https://doi.org/10.1021/acs.jchemed.0c00448 Zobrazit plný text záznamu