TIGER

Journal Articles: 8 results
Using Ozone in Organic Chemistry Lab: The Ozonolysis of Eugenol  Bruce M. Branan, Joshua T. Butcher, and Lawrence R. Olsen
This organic laboratory involves the ozonolysis of eugenol (clove oil) followed by a reductive workup that generates an aldehyde easily identified by its NMR and IR spectra.
Branan, Bruce M.; Butcher, Joshua T.; Olsen, Lawrence R. J. Chem. Educ. 2007, 84, 1979.
Aldehydes / Ketones |
Gases |
IR Spectroscopy |
Laboratory Equipment / Apparatus |
Natural Products |
NMR Spectroscopy |
Synthesis |
Oxidation / Reduction
A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl Compounds  Robert E. Rosenberg
Students teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones.
Rosenberg, Robert E. J. Chem. Educ. 2007, 84, 1474.
Addition Reactions |
Aldehydes / Ketones |
Esters |
Grignard Reagents |
IR Spectroscopy |
Oxidation / Reduction |
Reactions |
Student-Centered Learning
Enantioselective Reduction by Crude Plant Parts: Reduction of Benzofuran-2-yl Methyl Ketone with Carrot (Daucus carota) Bits  Silvana Ravía, Daniela Gamenara, Valeria Schapiro, Ana Bellomo, Jorge Adum, Gustavo Seoane, and David Gonzalez
Presents the enantioselective reduction of a ketone by crude plant parts, using carrot (Daucus carota) as the reducing agent.
Ravía, Silvana; Gamenara, Daniela; Schapiro, Valeria; Bellomo, Ana; Adum, Jorge; Seoane, Gustavo; Gonzalez, David. J. Chem. Educ. 2006, 83, 1049.
Aldehydes / Ketones |
Biotechnology |
Catalysis |
Chromatography |
Green Chemistry |
Oxidation / Reduction |
Stereochemistry |
Separation Science
Reductive Amination: A Remarkable Experiment for the Organic Laboratory  Kim M. Touchette
The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory.
Touchette, Kim M. J. Chem. Educ. 2006, 83, 929.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Green Chemistry |
Instrumental Methods |
IR Spectroscopy |
NMR Spectroscopy |
Oxidation / Reduction |
Solids
The Discovery-Oriented Approach to Organic Chemistry. 6. Selective Reduction in Organic Chemistry: Reduction of Aldehydes in the Presence of Esters Using Sodium Borohydride  Ashvin R. Baru and Ram S. Mohan
Describes two discovery oriented lab experiments involving the chemoselective reduction of vanillin acetate and methyl 4-formylbenzoate in the presence of esters using sodium borohydride, followed by product identification using 1H and 13C NMR spectroscopy.
Baru, Ashvin R.; Mohan, Ram S. J. Chem. Educ. 2005, 82, 1674.
NMR Spectroscopy |
Alcohols |
Aldehydes / Ketones |
Esters |
Oxidation / Reduction |
Thin Layer Chromatography |
Synthesis
A Microwave-Assisted Reduction of Cyclohexanone Using Solid-State-Supported Sodium Borohydride  Lori L. White and Kevin W. Kittredge
We report a microwave-assisted reduction of cyclohexanone by sodium borohydride that is supported on SiO2. The reaction was completed in less than 3 minutes. Workup and analysis by GCMS, IR, and 1H NMR was possible in a two and half-hour laboratory session. This reduction was used successfully in a second-year organic chemistry laboratory. Students were exposed to a green chemistry reaction using solid-state-supported reactants in the absence of solvent.
White, Lori L.; Kittredge, Kevin W. J. Chem. Educ. 2005, 82, 1055.
Oxidation / Reduction |
Solid State Chemistry |
Green Chemistry |
Alcohols |
Aldehydes / Ketones
Baker's Yeast Reduction of alpha-Diketones: A Four-Hour Experiment for Undergraduate Students  Besse, Pascale; Bolte, Jean; Veschambre, Henri
Procedure for quickly and efficiently reducing alpha-diketones using bakers' yeast.
Besse, Pascale; Bolte, Jean; Veschambre, Henri J. Chem. Educ. 1995, 72, 277.
Oxidation / Reduction |
Synthesis |
Aldehydes / Ketones
A More Affordable Undergraduate Experiment on the Reduction of Acetophenone by Yeast  Lee, Moses; Huntington, Martha
Preparation of Mosher's esters through the reduction of acetophenone with baker's yeast.
Lee, Moses; Huntington, Martha J. Chem. Educ. 1994, 71, A62.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Oxidation / Reduction |
Stereochemistry |
Chirality / Optical Activity |
Esters |
Synthesis