The Course Description for Advanced Organic Chemistry Lab, featuring the listed experiments, might
encompass the following topics: This laboratory course offers advanced practical experience in organic synthesis and
reaction mechanisms, building upon the foundational knowledge gained in introductory organic chemistry courses. The
experiments listed below are indicative of the sophisticated reactions and techniques covered in the course: 1.
Dibenzalacetone by the Aldol Condensation: Students will explore the aldol condensation reaction, synthesizing
dibenzalacetone from the condensation of two molecules of benzaldehyde in the presence of a base catalyst. This
experiment emphasizes the formation of carbon-carbon bonds and stereochemical considerations. 2. Diels-Alder
Reaction: Synthesis of Tetrahydrophthalic Anhydride: The Diels-Alder reaction, a powerful method for constructing cyclic
compounds, will be employed to synthesize tetrahydrophthalic anhydride from a conjugated diene and a dienophile. This
experiment highlights both the regioselectivity and stereoselectivity inherent in Diels-Alder reactions. 3. Synthesis of The
Sweetener Dulcin from The Analgesic Acetaminophen: Students will engage in a multistep synthesis to transform the
analgesic acetaminophen into the sweetener dulcin. This experiment involves various functional group transformations
and purification techniques. 4. Dilantin® and Benzilic Acid from Benzaldehyde: Through a series of reactions including
condensation, reduction, and rearrangement, students will synthesize Dilantin® (phenytoin) and benzilic acid from
benzaldehyde. This experiment showcases the application of diverse synthetic strategies to access complex molecules.
5. Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone: Students will investigate
photochemical reactions by performing the photoreduction of benzophenone to benzopinacol and subsequent
rearrangement to benzopinacolone. This experiment underscores the role of light in driving chemical transformations and
the mechanistic intricacies of photochemistry. Throughout the course, students will gain proficiency in advanced synthetic
techniques, including inert atmosphere reactions, chromatographic separations, and spectroscopic analyses (such as IR,
NMR, and UV-Vis spectroscopy) for compound characterization. Emphasis will be placed on critical thinking skills,
experimental design, and interpretation of results. Additionally, students will explore the underlying principles governing
organic reactions and mechanisms, deepening their understanding of organic chemistry concepts. Safety protocols and
good laboratory practices will be strictly enforced to ensure a safe and productive learning environment.