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... groups  More electrophilic carbonyl groups are more reactive to addition (acyl halides are most reactive, amides are least)  The intermediate with the best leaving group decomposes fastest Based on McMurry, Organic Chemistry, Chapter 21, 6th edition, (c) 2003 ...
Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution
Carboxylic Acid Derivatives and Nucleophilic Acyl Substitution

... groups  More electrophilic carbonyl groups are more reactive to addition (acyl halides are most reactive, amides are least)  The intermediate with the best leaving group decomposes fastest Based on McMurry, Organic Chemistry, Chapter 21, 6th edition, (c) 2003 ...
Full Text
Full Text

... functional groups is the hydroxyl group, which is present in a number of compounds of biological and synthetic interest, including nucleosides, carbohydrates, steroids, macrolides, polyethers, and the side chain of some amino acids or in large numbers of intermediates in total syntheses of complex n ...
Aldehydes, Ketones and Carboxylic acids
Aldehydes, Ketones and Carboxylic acids

... Aldehydes and ketones undergo nucleophilic substitution reaction. In nucleophilic substitution, a species that has extra electron or lone pair of electron attacks the carbonyl carbon of the ketone or the aldehyde leading to an alkoxide intermediate as shown in the middle figure below. This alkoxide ...
Enantioselective Organocatalytic Aminomethylation of Aldehydes: A
Enantioselective Organocatalytic Aminomethylation of Aldehydes: A

... gave a 72% yield of material with >98% ee. The benzyl groups were removed and replaced by Boc in an efficient one-pot operation. Jones oxidation12 then provided desired β2-amino acid product after simple extraction, with >50% overall yield from A. The route is short, and purifications are simple; th ...
EXPERIMENT 4 (Organic Chemistry II) Pahlavan/Cherif
EXPERIMENT 4 (Organic Chemistry II) Pahlavan/Cherif

... Under the hood place a small piece of sodium metal in to a beaker of water. Observe the reaction and after completion of the reaction, add 1 or 2 drops of phenolphthalein indicator to the solution in the beaker. Write a balance equation for the reaction of sodium and water. Repeat the reaction of 2 ...
document
document

... • Heating an alcohol to 170ºC with conc. H2SO4 produces an alkene as a water molecule is eliminated. • The acid acts as a catalyst ...
Boron and Metal Catalyzed CC and CH Bond Formation
Boron and Metal Catalyzed CC and CH Bond Formation

... Kabalka, for his guidance, patience, and financial support throughout my graduate school experience. He provided an ideal, stress-free environment to learn and practice chemistry. In addition, he taught me the finer parts of teaching others, and helped me pursue a future career during a difficult ec ...
An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol1
An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol1

... Assemble the Apparatus. To a 10-mL round-bottom flask add 0.360 g of racemic borneol , 1.0 mL of acetone, and 0.30 mL of glacial acetic acid. After adding a magnetic stir bar to the flask, attach an air condenser and place the round-bottom flask in a water bath at about 45 °C. It is important that t ...
Alcohols
Alcohols

... HYDROXIDE ION (OH-) WHICH IS A NEGATIVELY CHARGED PARTICLE FOUND IN BASES. IN BASES, THE HYDROXIDE ION IS HELD TO A POSITIVE ION BY AN A IONIC BOND. • ALCOHOLS HAVE THE GENERAL FORMULA CnH 2n+ 1OH ...
Disproportionation of Monolithium Acetylide into
Disproportionation of Monolithium Acetylide into

... used. With less reactive electrophiles such as chloro bis(diisopropylamino)borane [ClB(N-i-Pr2)2] (3j), reaction takes place efficiently at 0 °C to deliver boracetylene 4j in excellent yield. The latter transformation is particularly worthy of note since the reaction is by far less effective at -78 ...
Elimination Reactions
Elimination Reactions

... higher entropies than substitutions because eliminations have a greater number of products formed than that of starting compounds). • Any substitution that occurs must take place through an SN1 mechanism ...
Recent developments in the applications of palladium complexes
Recent developments in the applications of palladium complexes

... display remarkable performances in many other organic transformations such as polymerization, C-H activation processes or olefin hydrogenation. The numerous applications of Pd-NHC systems have been comprehensively reviewed.32-38 The development of new Pd-NHC complexes and the study of their applicat ...
Substitution and Elimination Reactions . 7.1. Definitions.
Substitution and Elimination Reactions . 7.1. Definitions.

... the starting material to a very crowded five-coordinate C in the TS, so the reaction is very sensitive to steric hindrance about the electrophilic C. Tertiary alkyl halides do not undergo SN2 substitution reactions! - See Jones, Table 7.1 Note also that nucleophiles can be neutral or anionic. Also n ...
Synthesis of [RuCl2(NO)2(THF)] and its Double CN BondForming
Synthesis of [RuCl2(NO)2(THF)] and its Double CN BondForming

... investigation, methods for controlling the reactivity of nitric oxide at transition-metal centers have received considerably less attention.[1–3] For example, the migratory insertion of NO into metal–alkyl or metal–aryl bonds has been observed in only a handful of metal complexes,[3] despite the ana ...
Asymmetric Catalytic Aldol
Asymmetric Catalytic Aldol

... contain a Zn2+ cofactor in the active site. • In both types of aldolases the formation of the enolate is rate determining. • These enzymes generally tolerate a broad range of acceptor substrates but have stringent requirements for the donor substrates. ...
RheniumCatalyzed Deoxydehydration of Diols and Polyols
RheniumCatalyzed Deoxydehydration of Diols and Polyols

... While the majority of oil, coal, and gas is used for energy production, the realization of an economy completely independent of fossil resources also requires biomass-based substitutes for polymers, medicine, pesticides, and so forth.[1] The evergrowing world population makes it questionable to use ...
Amino Alcohol Oxidation with Gold Catalysts: The Effect of Amino
Amino Alcohol Oxidation with Gold Catalysts: The Effect of Amino

... catalysts, represents a suitable alternative. The main problem lies on the high affinity of nitrogen for metal such as Pt or Pd, which lead to active sites blocking [7]. Gold catalyst appeared more resistant, and therefore applicable [8]. It has been shown, for example, that alaninol can be directly ...
Novel Brønsted-acidic ionic liquids based on benzothiazolium
Novel Brønsted-acidic ionic liquids based on benzothiazolium

... had many advantages over reactions catalyzed by conventional liquid or solid acids. In recent years, parallel to the rapid development of ILs, their applications in esterification have been extensively studied. For example, catalytic amounts of Brønsted-acidic ionic liquids promoted esterification, ...
Organic Chemistry Introduction
Organic Chemistry Introduction

... • Stabilize a high energy intermediate you stabilize the transition state leading to it ...
Chemistry 0310 - Organic Chemistry 1 Chapter 12. Reactions of
Chemistry 0310 - Organic Chemistry 1 Chapter 12. Reactions of

... - Syn-Hydroxylations of alkenes are most conveniently performed with catalytic OsO4 and NMO (N-methylmorpholine N-oxide) as co-oxidant. Attack occurs from the less-hindered face of the alkene, and a vicinal syn-diol is isolated after reductive workup. - Oxidative cleavage of 1,2-disubstituted alken ...
Alcohols, Thiols, and Ethers Ch#5
Alcohols, Thiols, and Ethers Ch#5

... The longest chain contains six carbon atoms, but it does not contain the carbon bonded to the hydroxyl group. The longest chain containing the carbon bonded to the —OH group is the one outlined by the green box, containing five carbon atoms. This chain is numbered from right to left in order to give ...
Solvent and Temperature Effects on the Reduction and Amination
Solvent and Temperature Effects on the Reduction and Amination

... Singaram, B. Org. Proc. Res. DeV. 2006, 10, 959. ...
Alcohols Phenols and Ethers
Alcohols Phenols and Ethers

... An ether cannot form hydrogen bonds with other ether molecules since there is no H to be donated (no -OH group) Ethers can be involved in H-bonding with systems able to donate H (e.g. water). The implications of these effects are: lower melting and boiling points compared to analogous alcohols solub ...
Chapter 7- Alcohols
Chapter 7- Alcohols

... Example of a substituted reaction (OH replaced by X) Good synthetic route to alkyl halides Rate depends on degree of substitution 3o > 2o > 1o ...
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Elias James Corey



Elias James ""E.J."" Corey (born July 12, 1928) is an American organic chemist. In 1990, he won the Nobel Prize in Chemistry ""for his development of the theory and methodology of organic synthesis"", specifically retrosynthetic analysis. Regarded by many as one of the greatest living chemists, he has developed numerous synthetic reagents, methodologies and total syntheses and has advanced the science of organic synthesis considerably.
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