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- Second-year undergraduate (5)
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- Acylation (2)
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- Acetals (1)
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- Allylation (1)
- Amino Acids (1)
- Biginelli reaction (1)
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- Bismuth and compounds; Green chemistry; Dihydrobenzopyrans; Bismuth triflate. (1)
Articles 1 - 30 of 33
Full-Text Articles in Chemistry
Iron (Iii) Tosylate Catalyzed Synthesis Of 3,4-Dihydropyrimidin-2(1h)-Ones/Thiones, Ram Mohan, Jacob Starcevich, Thomas Laughlin
Iron (Iii) Tosylate Catalyzed Synthesis Of 3,4-Dihydropyrimidin-2(1h)-Ones/Thiones, Ram Mohan, Jacob Starcevich, Thomas Laughlin
Scholarship
No abstract provided.
Iron(Iii) Tosylate Catalyzed Acylation Of Alcohols, Phenols, And Aldehydes, Ram Mohan, Neil Baldwin, Anna Nord, Brendan O’Donnell
Iron(Iii) Tosylate Catalyzed Acylation Of Alcohols, Phenols, And Aldehydes, Ram Mohan, Neil Baldwin, Anna Nord, Brendan O’Donnell
Scholarship
Iron(III) p-toluenesulfonate (tosylate) is an efficient catalyst for acetylation of alcohols, phenols, and aldehydes. The acetylation of 1° and 2° alcohols, diols, and phenols proceeded smoothly with 2.0 mol % of catalyst. However, the reaction worked well with only a few 3° alcohols. The methodology was also applicable to the synthesis of a few benzoate esters but required the use of 5.0 mol % catalyst. Aldehydes could also be converted into the corresponding 1,1-diesters (acylals) under the reaction conditions. Iron(III) tosylate is an inexpensive, and easy to handle, commercially available catalyst.
A Discovery-Oriented Approach To Solid-Phase Peptide Synthesis, Brian Brennan, Matthew Bockman, Christopher Miedema
A Discovery-Oriented Approach To Solid-Phase Peptide Synthesis, Brian Brennan, Matthew Bockman, Christopher Miedema
Scholarship
In this discovery-oriented laboratory experiment, students use solid-phase synthesis techniques to construct a dipeptide containing an unknown amino acid. Following synthesis and cleavage from the polymeric support, electrospray ionization-mass spectrometry is employed to identify the unknown amino acid that was used in the peptide coupling. This experiment, performed in two, 3-h laboratory periods, provides an opportunity for students to learn the technique of solid-phase peptide synthesis and to critically evaluate data that they generate in the laboratory. The experiment is suitable for second-semester organic chemistry students as they learn methods for the formation of amide bonds or upper-level biochemistry students …
A Mild And Chemoselective Method For The Deprotection Of Tert-Butyldimethylsilyl (Tbdms) Ethers Using Iron(Iii) Tosylate As A Catalyst, Ram Mohan, Jason Bothwell, Veronica Angeles, James Carolan, Margaret Olson
A Mild And Chemoselective Method For The Deprotection Of Tert-Butyldimethylsilyl (Tbdms) Ethers Using Iron(Iii) Tosylate As A Catalyst, Ram Mohan, Jason Bothwell, Veronica Angeles, James Carolan, Margaret Olson
Scholarship
The most common method for the deprotection ofTBDMS ethers utilizes stoichiometric amounts of tetrabutylammonium fluoride, n-Bu4N+F(TBAF), which is highly corrosive and toxic. We have developed a mild and chemoselective method for the deprotection ofTBDMS, TES, and TIPS ethers using iron(III) tosylate as a catalyst. Phenolic TBDMS ethers, TBDPS ethers and the BOC group are not affected under these conditions. Iron(III) tosylate is an inexpensive, commercially available, and non-corrosive reagent.
Bismuth(Iii) Bromide In Organic Synthesis. A Catalytic Method For The Allylation Of Tetrahydrofuranyl And Tetrahydropyranyl Ethers, Ram Mohan, Scott Krabbe, Veronica Angeles
Bismuth(Iii) Bromide In Organic Synthesis. A Catalytic Method For The Allylation Of Tetrahydrofuranyl And Tetrahydropyranyl Ethers, Ram Mohan, Scott Krabbe, Veronica Angeles
Scholarship
A bismuth bromide-catalyzed (10.0 mol %) multicomponent reaction involving the allylation of THF- and THP-ethers, followed by in situ derivatization with acetic anhydride to generate highly functionalized esters has been developed under solvent-free conditions. To the best of our knowledge, this is the first report of a catalytic procedure for the allylation of THF- and THP-ethers to yield ring-opened products.
Iron(Iii) Tosylate-Catalyzed Deprotection Of Aromatic Acetals In Water, Ram Mohan, Margaret Olson, James Carolan, Michael Chiodo, Phillip Lazzara
Iron(Iii) Tosylate-Catalyzed Deprotection Of Aromatic Acetals In Water, Ram Mohan, Margaret Olson, James Carolan, Michael Chiodo, Phillip Lazzara
Scholarship
The deprotection of aromatic as well as conjugated acetals and ketals in water is catalyzed by iron(III) tosylate (1.0–5.0 mol %). Iron(III) tosylate is an inexpensive and readily available catalyst. The use of water, the most environmentally benign solvent, makes this procedure especially attractive for acetal deprotection.
In Your Element: Green Bismuth, Ram Mohan
Environmentally Friendly Organic Synthesis Using Bismuth Compounds. Bismuth(Iii) Bromide Catalyzed Synthesis Of Substituted Tetrahydroquinoline Derivatives, Ram Mohan, Jamie Rogers, Justin Ernat, Herbie Yung
Environmentally Friendly Organic Synthesis Using Bismuth Compounds. Bismuth(Iii) Bromide Catalyzed Synthesis Of Substituted Tetrahydroquinoline Derivatives, Ram Mohan, Jamie Rogers, Justin Ernat, Herbie Yung
Scholarship
The bismuth bromide catalyzed synthesis of a range of substituted tetrahydroquinoline derivatives via a three component coupling reaction between substituted anilines and enol ethers is reported. Bismuth compounds are attractive for use as catalysts because of their remarkably low toxicity. Bismuth bromide is relatively inexpensive and easy to handle, and hence preferable to other corrosive catalysts previously used for synthesis of tetrahydroquinoline derivatives.
The Discovery-Oriented Approach To Organic Chemistry. 7. Rearrangement Of Trans-Stilbene Oxide With Bismuth Trifluoromethanesulfonate And Other Metal Triflates, Ram Mohan, James Christensen, Matthew Huddle, Jamie Rogers, Herbie Yung
The Discovery-Oriented Approach To Organic Chemistry. 7. Rearrangement Of Trans-Stilbene Oxide With Bismuth Trifluoromethanesulfonate And Other Metal Triflates, Ram Mohan, James Christensen, Matthew Huddle, Jamie Rogers, Herbie Yung
Scholarship
A microscale discovery-oriented experiment illustrating the rearrangement of trans-stilbene oxide using non-corrosive metal triflates as catalysts has been developed. The use of CDCl3 as the reaction solvent eliminates the need for any workup and avoids the use of highly toxic boron trifluoride etherate as a catalyst and additional reaction solvent.
Environmentally Friendly Organic Synthesis Using Bismuth Compounds: Bismuth(Iii) Iodide Catalyzed Deprotection Of Acetals In Water, Ram Mohan, Aaron Bailey, Ashvin Baru, Kendall Tashe
Environmentally Friendly Organic Synthesis Using Bismuth Compounds: Bismuth(Iii) Iodide Catalyzed Deprotection Of Acetals In Water, Ram Mohan, Aaron Bailey, Ashvin Baru, Kendall Tashe
Scholarship
The chemoselective deprotection of a wide range of acetals and ketals in water is catalyzed by bismuth(III) iodide. Bismuth(III) compounds are remarkably nontoxic and hence are attractive as environmentally friendly catalysts.
Iron(Iii) P-Toluenesulfonate Catalyzed Synthesis Of Homoallyl Ethers From Acetals And Aldehydes, Ram Mohan, Matthew Spafford, Erin Anderson, Joshua Lacey, Ann Palma
Iron(Iii) P-Toluenesulfonate Catalyzed Synthesis Of Homoallyl Ethers From Acetals And Aldehydes, Ram Mohan, Matthew Spafford, Erin Anderson, Joshua Lacey, Ann Palma
Scholarship
Iron(III) p-toluenesulfonate, Fe(OTs)3.6H20, is an inexpensive, versatile and commercially available catalyst for the allylation of acetals using allyltrimethylsilane to yield homoallyl ethers in moderate to good yields. The one-pot conversion of aldehydes to homoallyl ethers using alkoxysilanes has also been accomplished using Fe(OTs)3.6H20 as a catalyst. The use of mild reaction conditions and a relatively non-corrosive catalyst make this method an attractive option for the synthesis of a range of homoallyl ethers.
Reactivity Of Ionic Liquids, Ram Mohan, Shahana Chowdhury, Janet Scott
Reactivity Of Ionic Liquids, Ram Mohan, Shahana Chowdhury, Janet Scott
Scholarship
Ionic liquids are becoming widely used in synthetic organic chemistry and yet relatively little attention has been paid to the intrinsic reactivity of these low temperature molten salts. Clues to the non-innocent nature of many ionic liquids are contained in the reports of altered reactivity of dissolved substrates, unexpected catalytic activity and unforeseen by-product formation. In this review, we focus on the reactivity of ionic liquids, as opposed to reactivity in ionic liquids (although discussion of the latter is often included where it aids understanding of the former).
Environment Friendly Organic Synthesis Using Bismuth Compounds. An Efficient Method For Carbonyl-Ene Reactions Catalyzed By Bismuth Triflate, Ram Mohan, Erin Anderson, Justin Ernat, Mai Nguyen, Ann Palma
Environment Friendly Organic Synthesis Using Bismuth Compounds. An Efficient Method For Carbonyl-Ene Reactions Catalyzed By Bismuth Triflate, Ram Mohan, Erin Anderson, Justin Ernat, Mai Nguyen, Ann Palma
Scholarship
Bismuth triflate (0.1 mol %) is a highly efficient catalyst for the cyclization of citronellal 1, a reaction that yields a ratio of 80:20 of isopulegol 2 and neoisopulegol 3. This methodology has also been extended to the synthesis of substituted piperidines. The bismuth triflate catalyzed ene reaction of aldehyde 4 gives a 70:30 mixture of piperidines 5 and 6. The advantages of these methods include the use of a highly efficient catalyst that is relatively nontoxic, cheap and easy to handle.
A Study Of Epoxyolefin Cyclizations Catalyzed By Bismuth Trifluoromethanesulfonate And Other Metal Triflates, Ram Mohan, Joshua Lacey, Peter Anzalone, Christopher Duncan, Matthew Hackert
A Study Of Epoxyolefin Cyclizations Catalyzed By Bismuth Trifluoromethanesulfonate And Other Metal Triflates, Ram Mohan, Joshua Lacey, Peter Anzalone, Christopher Duncan, Matthew Hackert
Scholarship
Epoxyolefin cyclizations have attracted considerable interest due to their importance in biosynthetic pathways. Bismuth trifluoromethanesulfonate as well as several other metal triflates are shown to be highly effective (0.1 mol %) catalysts for the cyclization of geraniolene oxide. The product composition is found to be more dependent on solvent and substrate concentration than on the nature of the metal triflate. Cyclization products are favored in CH2Cl2 and under high dilution conditions. Ether solvents favored acyclic products.
The Discovery-Oriented Approach To Organic Chemistry. 6. Selective Reduction In Organic Chemistry: Reduction Of Aldehydes In The Presence Of Esters Using Sodium Borohydride, Ram Mohan, Ashvin Baru
The Discovery-Oriented Approach To Organic Chemistry. 6. Selective Reduction In Organic Chemistry: Reduction Of Aldehydes In The Presence Of Esters Using Sodium Borohydride, Ram Mohan, Ashvin Baru
Scholarship
Chemoselective reductions are valuable in organic synthesis and are routinely discussed in a sophomore organic chemistry course. Yet, there are few examples of laboratory experiments that illustrate such chemoselectivity. A reaction that is routinely discussed in sophomore organic chemistry is the selective reduction of aldehydes and ketones using sodium borohydride. Esters are typically not affected by NaBH4. However, none of the lab experiments reported to date illustrate this chemoselectivity (1). We have developed a discovery-oriented lab experiment that illustrates the chemoselective nature of reductions using sodium borohydride. The experiments involve the reduction of vanillin acetate (Scheme I) and methyl 4-formylbenzoate …
Bismuth Compounds In Organic Synthesis. Bismuth Nitrate Catalyzed Chemoselective Synthesis Of Acylals From Aromatic Aldehydes, Ram Mohan, David Aggen, Joshua Arnold, Patrick Hayes, Nathaniel Smoter
Bismuth Compounds In Organic Synthesis. Bismuth Nitrate Catalyzed Chemoselective Synthesis Of Acylals From Aromatic Aldehydes, Ram Mohan, David Aggen, Joshua Arnold, Patrick Hayes, Nathaniel Smoter
Scholarship
Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 3–10 mol% Bi(NO3)3•5H2O. Ketones are not affected under the reaction conditions. The relatively non-toxic nature of the catalyst, its ease of handling, easy availability and low cost make this procedure especially attractive for large-scale synthesis.
Environment-Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Triflate Catalyzed Synthesis Of Substituted 3,4-Dihydro-2h-L-Benzopyrans, Ram Mohan, Mai Nguyen, Joshua Arnold, Katherine Peterson
Environment-Friendly Organic Synthesis Using Bismuth Compounds. Bismuth Triflate Catalyzed Synthesis Of Substituted 3,4-Dihydro-2h-L-Benzopyrans, Ram Mohan, Mai Nguyen, Joshua Arnold, Katherine Peterson
Scholarship
A highly catalytic method for the synthesis of dihydrobenzopyrans from salicylaldehydes has been developed. An extension of this method to the synthesis of a pyrano [2,3,b]benzopyran has also been achieved. Bi(OTf)3.xH2O (1< x < 4) (0.1mol%) smoothly catalyzes the condensation of substituted salicylaldehydes with 2,2-dimethoxypropane to give the corresponding substituted 3,4-dihydro-2H-1-benzopyrans as a mixture of diastereomers (9:1) in moderate yields. The relative configuration of the methoxy groups in the two diastereomers was established by NOE experiments. The advantages of this method include the use of an easy to handle, inexpensive and relatively non-toxic catalyst.
Bismuth Compounds In Organic Synthesis. Deprotection Of Ketoximes Using Bismuth Bromide-Bismuth Triflate, Ram Mohan, Joshua Arnold, Patrick Hayes, Robert Kohaus
Bismuth Compounds In Organic Synthesis. Deprotection Of Ketoximes Using Bismuth Bromide-Bismuth Triflate, Ram Mohan, Joshua Arnold, Patrick Hayes, Robert Kohaus
Scholarship
Ketoximes undergo deprotection in CH3CN/acetone/H2O (3:6:1) in the presence of 20–40 mol% BiBr3/5 mol% Bi(OTf)3. Bismuth(III) salts are relatively non-toxic, insensitive to air and inexpensive. These features coupled with the use of a relatively non-toxic solvent system make this method an attractive alternative to existing routes for deprotection of ketoximes.
Bismuth Compounds In Organic Synthesis. Synthesis Of Resorcinarenes Using Bismuth Triflate, Ram Mohan, Katherine Peterson, Russell Smith
Bismuth Compounds In Organic Synthesis. Synthesis Of Resorcinarenes Using Bismuth Triflate, Ram Mohan, Katherine Peterson, Russell Smith
Scholarship
Bismuth triflate (5 mol%) smoothly catalyzes the condensation of aromatic and aliphatic aldehydes with resorcinol to give tetrameric cyclic products, resorcinarenes. With benzaldehyde, the product is obtained as a mixture of two diastereomers and the ratio of the diastereomers depends on reaction time. On the other hand, a single diastereomer is obtained with aliphatic aldehydes. The low toxicity and ease of handling of bismuth compounds coupled with fast reaction times make this method an attractive alternative to the existing methods for resorcinarene formation
Applications Of Bismuth(Iii) Compounds In Organic Synthesis, Ram Mohan, Nicholas Leonard, Laura Wieland
Applications Of Bismuth(Iii) Compounds In Organic Synthesis, Ram Mohan, Nicholas Leonard, Laura Wieland
Scholarship
No abstract provided.
Bismuth Triflate Catalyzed Allylation Of Acetals: A Simple And Mild Method For Synthesis Of Homoallyl Ethers, Ram Mohan, Laura Wieland, Herbert Zerth
Bismuth Triflate Catalyzed Allylation Of Acetals: A Simple And Mild Method For Synthesis Of Homoallyl Ethers, Ram Mohan, Laura Wieland, Herbert Zerth
Scholarship
The allylation of acetals using allyltrimethylsilane is efficiently catalyzed by bismuth triflate (1.0 mol%). The reaction proceeds smoothly at room temperature to afford the corresponding homoallyl ether in good yield. The mild reaction conditions, the low toxicity of bismuth salts, and the high catalytic efficiency of the system make this procedure particularly attractive for large-scale synthesis.
A Facile And Efficient Method For The Rearrangement Of Aryl-Substituted Epoxides To Aldehydes And Ketones Using Bismuth Triflate, Ram Mohan, Kaushik Bhatia, Kyle Eash, Nicholas Leonard, Matthew Oswald
A Facile And Efficient Method For The Rearrangement Of Aryl-Substituted Epoxides To Aldehydes And Ketones Using Bismuth Triflate, Ram Mohan, Kaushik Bhatia, Kyle Eash, Nicholas Leonard, Matthew Oswald
Scholarship
Aryl-substituted epoxides undergo smooth rearrangement in the presence of 0.01–0.1 mol% Bi(OTf)3•xH2O. The rearrangement is regioselective with aryl-substituted epoxides, and products arise from cleavage of the benzylic C―O bond. The highly catalytic nature of this method coupled with the fact that the reagent is relatively non-toxic, easy to handle and inexpensive make it an attractive alternative to more corrosive and toxic Lewis acids, such as BF3•Et2O, currently used to effect epoxide rearrangements.
The Discovery-Oriented Approach To Organic Chemistry. 5. Stereochemistry Of E2 Elimination: Elimination Of Cis- And Trans-2-Methylcyclohexyl Tosylate, Ram Mohan, Marcus Cabay, Brad Ettlie, Adam Tuite, Kurt Welday
The Discovery-Oriented Approach To Organic Chemistry. 5. Stereochemistry Of E2 Elimination: Elimination Of Cis- And Trans-2-Methylcyclohexyl Tosylate, Ram Mohan, Marcus Cabay, Brad Ettlie, Adam Tuite, Kurt Welday
Scholarship
The E2 elimination is one of the most important reactions in organic chemistry and is discussed in considerable detail in a sophomore organic course. We have developed a discovery-oriented lab that illustrates the stereochemistry of the E2 elimination reaction and is a good exercise in 1H NMR spectroscopy. The added element of discovery insures that student interest and enthusiasm are retained.
An Efficient Method For The Chemoselective Synthesis Of Acylals From Aromatic Aldehydes Using Bismuth Triflate, Ram Mohan, Marc Carrigan, Kyle Eash, Matthew Oswald
An Efficient Method For The Chemoselective Synthesis Of Acylals From Aromatic Aldehydes Using Bismuth Triflate, Ram Mohan, Marc Carrigan, Kyle Eash, Matthew Oswald
Scholarship
Aromatic aldehydes are smoothly converted into the corresponding acylals in good yields in the presence of 0.10 mol% Bi(OTf)3•xH2O. Ketones are not affected under the reaction conditions. The highly catalytic nature of bismuth triflate and the fact that it is relatively non-toxic, easy to handle and insensitive to small amounts of air and moisture makes this procedure especially attractive for large-scale synthesis.
The Discovery-Oriented Approach To Organic Chemistry. 4. Epoxidation Of P-Methoxy-Trans-Β-Methylstyrene. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Rebecca Centko
The Discovery-Oriented Approach To Organic Chemistry. 4. Epoxidation Of P-Methoxy-Trans-Β-Methylstyrene. An Exercise In 1H Nmr And 13C Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Rebecca Centko
Scholarship
Epoxidation of alkenes using peroxyacids is one of the most fundamental reactions in organic chemistry, yet there are very few examples of laboratory experiments that illustrate this important reaction. We have developed a discovery-oriented lab experiment that illustrates epoxidation of alkenes as well as the reactivity of epoxides toward acids. The experiment involves reaction of p-methoxy-trans-β-methylstyrene (trans-anethole) with m-chloroperoxybenzoic acid (MCPBA), in both the absence and presence of a buffer, followed by product identification using 1H NMR, 13C NMR, and IR spectroscopy. The added element of discovery ensures that students' interest and enthusiasm are retained.
Deprotection Of Ketoximes Using Bismuth(Iii) Nitrate Pentahydrate, Ram Mohan, Bryce Nattier, Kyle Eash
Deprotection Of Ketoximes Using Bismuth(Iii) Nitrate Pentahydrate, Ram Mohan, Bryce Nattier, Kyle Eash
Scholarship
Ketoximes undergo facile deprotection in acetone-H20 (9: 1) in the presence 01' 0.5 equivalents of Bi(N03h•5H20. Bismuth(III) nitrate is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the use of a relatively nontoxic solvent system make this method an attractive alternative to existing routes for deprotection of ketoximes.
Bismuth(Iii) Oxide Perchlorate Promoted Rearrangement Of Epoxides To Aldehydes And Ketones, Ram Mohan, Andrew Anderson, Jesse Blazek, Parie Garg, Brian Payne
Bismuth(Iii) Oxide Perchlorate Promoted Rearrangement Of Epoxides To Aldehydes And Ketones, Ram Mohan, Andrew Anderson, Jesse Blazek, Parie Garg, Brian Payne
Scholarship
Aryl-substituted epoxides and aliphatic epoxides with a tertiary epoxide carbon undergo smooth rearrangement in the presence of 10–50 mol% bismuth(III) oxide perchlorate, BiOClO4•xH2O, to give carbonyl compounds. The rearrangement is regioselective with aryl substituted epoxides and a single carbonyl compound arising from cleavage of benzylic C―O bond is formed. BiOClO4•xH2O is relatively non-toxic, insensitive to air and inexpensive, making this catalyst an attractive alternative to more corrosive and toxic Lewis acids such as BF3•Et2O or InCl3 currently used to effect epoxide rearrangements.
The Discovery-Oriented Approach To Organic Chemistry. 3. Boron-Trifluoride Catalyzed Rearrangement Of Cis- And Trans-Stilbene Oxides. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Erik Sgariglia, Regina Schopp, Kostas Gavardinas
The Discovery-Oriented Approach To Organic Chemistry. 3. Boron-Trifluoride Catalyzed Rearrangement Of Cis- And Trans-Stilbene Oxides. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Erik Sgariglia, Regina Schopp, Kostas Gavardinas
Scholarship
Epoxides, or oxiranes, are among the most versatile intermediates in organic synthesis. Yet very few examples of laboratory experiments involving reactions of epoxides are to be found in lab texts. We have developed a discovery-oriented laboratory experiment that involves the rearrangement of both cis- and trans-stilbene oxides with boron trifluoride etherate. The identity of the product can be easily determined by 1H NMR spectroscopy and, in case of the trans isomer, by preparation of the semicarbazone derivative as well. In spite of the simplicity of the experiment, the element of discovery ensures that student interest and enthusiasm are retained.
Isolation Of Curcumin From Tumeric, Ram Mohan, Andrew Anderson, Matthew Mitchell
Isolation Of Curcumin From Tumeric, Ram Mohan, Andrew Anderson, Matthew Mitchell
Scholarship
No abstract provided.
The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Steven Shadwick
The Discovery-Oriented Approach To Organic Chemistry. 2. Selectivity In Alcohol Oxidation. An Exercise In 1H Nmr Spectroscopy For Sophomore Organic Laboratories, Ram Mohan, Steven Shadwick
Scholarship
We have developed a simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine. 1H NMR analysis of the product mixture allows the student to determine the selectivity exhibited by the reagent.