Synthesis and Metalation of a Ligand: An Interdisciplinary Laboratory Experiment for Second-Year Organic and Introductory Inorganic Chemistry Students

Abstract

An interdisciplinary laboratory experiment involving second-year undergraduate organic chemistry and introductory inorganic chemistry undergraduate students is described. Organic chemistry students prepare a series of amine-bis(phenols) via a Mannich reaction, and characterize their products using melting point; FTIR; and 1 H, 13 C, DEPT-135, and HSQC NMR experiments. In the inorganic chemistry laboratory, students utilize these amine ligands to prepare a series of octahedral titanium complexes, and characterize the resultant complexes using FTIR, and 1 H, 13 C, DEPT-135, and HSQC NMR spectroscopy. Students are asked to revisit concepts such as the two-and three-dimensional representations of their target molecules and reaction mechanisms throughout both experiments. From these experiments, students gain an appreciation for the multidisciplinary nature of chemistry.

Synthesis and Use of Ethyl 6-Acetyloxyhexanoate as an Internal Standard: An Interdisciplinary Experiment for an Undergraduate Chemistry Laboratory

“…Further to this, such a laboratorysynthesizing a chemical to then be used in an analytical experimentdemonstrates the utility and value of making a compound to be used in further investigations. This is very different from traditional organic synthetic laboratories, which are typically “synthesize and discard” . Similarly, analytical chemistry experiments most frequently use purchased chemical standards rather than standards that have been made by the studentthis fosters the idea that all required chemicals are commercially available, which is most definitely not the case.…”

“…For this reason, it is becoming increasingly important to provide interdisciplinary laboratory experiments and courses for undergraduate students. Not only does such an offering expose students to real-life situations, often emulating processes that may be involved in their future career, but it also increases understanding of theoretical material and facilitates enhanced student engagement and interest in course material. − Furthermore, it introduces to students the concept that while often taught separately, there is extensive and increasing overlap in the various disciplines within chemistry . The combining of several aspects of chemistry allows students to view these areas of study as interrelated, rather than disconnectedsuch a perception enables students to perceive bigger-picture questions in a new light and solve the problems that are posed to them in a more informed manner. ,, …”

“…3 The combining of several aspects of chemistry allows students to view these areas of study as interrelated, rather than disconnectedsuch a perception enables students to perceive bigger-picture questions in a new light and solve the problems that are posed to them in a more informed manner. 3,7,8 For these aforementioned reasons, the pairing of an organic synthesis-focused and analytical-focused experiment is an excellent learning opportunity for students. Further to this, such a laboratorysynthesizing a chemical to then be used in an analytical experimentdemonstrates the utility and value of making a compound to be used in further investigations.…”

Expanding the Scope of an Electrophilic Aromatic Substitution Discovery Experiment Including Hydride and Methyl Shifts

“…In one case the authors put forth a multistep reaction in which students generate metal ligands in organic chemistry then metalate them in their inorganic chemistry course, an attractive variation connecting multiple courses in the curriculum. 24 Carbocations and their behavior also continue to fascinate, 25 carbocation structures 26 including the isobornyl system. 27 Faculty may consider options for mining textbooks 28 or the research literature 29 for descriptions of carbocations, including analysis of their stabilizing features such as resonance, hyperconjugation, and induction; in many cases these are supported by computational chemistry approaches.…”

“…Some of these offerings include computational exercises in which students investigate relative reactivities and product distributions; others incorporate EAS in a multistep reaction sequence. In one case the authors put forth a multistep reaction in which students generate metal ligands in organic chemistry then metalate them in their inorganic chemistry course, an attractive variation connecting multiple courses in the curriculum …”