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Synthesis of Ibuprofen in the Introductory Organic Laboratory
Organic chemistry: “Introduction to amines”. Amine nomenclature. and of amines. Synthesis of amines—through SN2, through lithium aluminum hydride (LAH) reduction of amides or , through the Gabriel synthesis, or through reductive . Overview of LAH reductions—of and , of carboxylic acids, of esters, of amides, and of .
Our programs are tied by the common theme of organic synthesis. We are interested in the development of new reactions and reagents for natural product total synthesis, and we have contributed a variety of new reactions to the chemist's arsenal, including free radical-mediated aryl and vinyl amination, the Brønsted acid-catalyzed aza-Darzens reaction, and a new acid catalyzed olefin aminoacyloxylation reaction. We also apply these reactions to the targets that inspired them. For example, our synthesis of mitomycin C uses the acid-catalyzed aza-Darzens reaction, in addition to a regioselective enamine-quinone coupling. And in our approach to (+)-zwittermicin A, we deploy a variation of our Brønsted acid catalyzed azide-olefin addition. As a result, we are able to synthesize highly functionalized, stereochemically dense advanced intermediates with considerable brevity. We reported the first total synthesis of (+)-serratezomine A using the free radical-mediated vinyl amination reaction, which provided this challenging target in a mere 15 steps (longest linear sequence).
Experimental Organic Chemistry - 1st Edition
Organic chemistry: “Ethers”. Ethers. Williamson ether synthesis (preparation of ethers via SN2); . Digression on how to remember the -Lowry and Lewis definitions of acids and bases. Cleavage of ethers with (HX). Effect of positive formal charges on reactivity. Effect of acid or base on reactivity.
Organic chemistry: “”. How to make and alkyl (). Reactions of and alkyl (with solvents, and , and ). Synthesis problems—using radical , E2, SN2, oxidation (PCC), and for synthesis. The “” technique for solving synthesis problems.
Advanced Organic Synthesis: A Laboratory Manual - …
The dissociative chemisorption of methane on a metal catalyst is the rate limiting step in the steam reforming of natural gas, our primary source for the molecular hydrogen used in the Haber-Bosch process. In collaboration with the experimental group of Rainer Beck at the École Polytechnic Fédéral de Lausanne, we examined this reaction on a Pt surface containing step defects. We were able to differentiate between reactions at the step edges and the terrace sites, using both UHV molecular beam experiments and high-dimensional quantum scattering theory. Both approaches were also able to resolve the reaction probability with respect to the velocity and vibrational state of the methane molecule and the surface temperature, providing additional details about the reaction mechanism.
Our research focuses on developing new tools to broaden our fundamental understanding of chemistry while addressing problems significant to human health. To achieve this objective, we divide our efforts between two broadly defined areas, bio- and glycoconjugate assembly and natural product total synthesis. Since our goal is to interface our synthetic efforts with issues of therapeutic application, we value interdisciplinary collaborations with biologists who aid in evaluation of the molecules we prepare. This approach, which is fostered by the Vanderbilt Institute of Chemical Biology, is a critical aspect of our program.
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Advanced Organic Synthesis: A Laboratory ..
Organic chemistry: “Reactions of and ”. formation through attack of secondary amines on and ; as ; of ; synthesis problems involving . condensation; crossed condensation; condensation. condensation; condensation; crossed condensation; condensation as a route to . ester synthesis; ester synthesis. Michael addition; Michael acceptors; Michael donors
This syllabus section provides an ..
Organic chemistry: “Carboxylic acids and acid derivatives”. Acidity of carboxylic acids; ranking compounds in order of acidity. How to synthesize carboxylic acids: oxidation; carbonation; hydrolysis. The types of carboxylic acid derivative. The general pattern for attack on carboxylic acids and acid derivatives (addition-elimination). . Ranking carboxylic acids derivatives in order of reactivity
Introduction to Organic Synthesis Laboratory ..
Organic chemistry: “More on and ”. attack on and ; the three main categories of attack. Two category 1 reactions: attack by a Grignard to form an alcohol; attack by LAH to form an alcohol. A category 2 reaction: attack by alcohol in acidic conditions to form an or . A category 2 “reverse” reaction: reaction of an or with aqueous acid to form an or
asymmetric cycloaddition reaction.
Organic chemistry: “ synthesis and reactions”. of carbons; acidity of alkynes; use of anions as for SN2 reactions and for attack on (). synthesis from by double elimination; synthesis from alkenes by -double . reactions. Hydrogenation of alkynes; hydrogenation of with catalyst to form alkenes; sequential one-electron reduction of alkynes with sodium metal to form trans alkenes. addition of HX to alkynes; addition of X2 to alkynes (). ; ; mercuric ion-catalyzed hydration of alkynes to form
Organic synthesis is a special branch of chemical synthesis ..
Organic chemistry: “ of alkenes”. addition reactions. Addition of OsO4 (osmium ) to achieve . Using to achieve anti . A synthesis problem. The synthetic toolbox. When does hindrance block one face of a planar intermediate?
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