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... not only one of the most valuable reagents for electrophilic fluorination but also a versatile mediator or catalyst for various other functionalisations of organic compounds. Its application for selective and effective iodination, bromination, chlorination, nitration and thiocyanation of a comprehen ...
... not only one of the most valuable reagents for electrophilic fluorination but also a versatile mediator or catalyst for various other functionalisations of organic compounds. Its application for selective and effective iodination, bromination, chlorination, nitration and thiocyanation of a comprehen ...
Chapter 17 Allylic and Benzylic Reactivity
... Compound (1) reacts most rapidly because the carbocation intermediate is not destabilized by the deactivating polar effect of a chloro substituent, which outweighs its resonance effect. ...
... Compound (1) reacts most rapidly because the carbocation intermediate is not destabilized by the deactivating polar effect of a chloro substituent, which outweighs its resonance effect. ...
Nuggets of Knowledge for Chapter 13 – Alcohols (II)
... OH is not a good leaving group, so nucleophiles cannot attack them. o Reduction: Although in theory the alcohol could lose a bond to oxygen, there are no reagents available to accomplish this reaction (the only way to do this is using more than one step). ...
... OH is not a good leaving group, so nucleophiles cannot attack them. o Reduction: Although in theory the alcohol could lose a bond to oxygen, there are no reagents available to accomplish this reaction (the only way to do this is using more than one step). ...
Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to
... Dissolving aldehydes or ketones in water causes formation of an equilibrium between the carbonyl compound and its hydrate l The hydrate is also called a gem-diol l The equilibrum favors a ketone over its hydrate because the tetrahedral ketone hydrate is stericallycrowded l Aqueous solution of formal ...
... Dissolving aldehydes or ketones in water causes formation of an equilibrium between the carbonyl compound and its hydrate l The hydrate is also called a gem-diol l The equilibrum favors a ketone over its hydrate because the tetrahedral ketone hydrate is stericallycrowded l Aqueous solution of formal ...
Remodeling of the natural product fumagillol
... reasonable reaction times, presumably due to the greater basicity of these amines leading to tighter interaction with the catalyst. An even greater reduction in reaction rate was observed with Zn(II) catalysis, rendering the reaction unacceptably slow (60 h, approx. 5-10% conversion). Use of Mg(OTf ...
... reasonable reaction times, presumably due to the greater basicity of these amines leading to tighter interaction with the catalyst. An even greater reduction in reaction rate was observed with Zn(II) catalysis, rendering the reaction unacceptably slow (60 h, approx. 5-10% conversion). Use of Mg(OTf ...
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... dehydrohalogenation, the major product is the more stable stereoisomer. • A reaction is stereoselective when it forms predominantly or exclusively one stereoisomer when two or more are possible. • The E2 reaction is stereoselective because one stereoisomer is formed preferentially. Why? ...
... dehydrohalogenation, the major product is the more stable stereoisomer. • A reaction is stereoselective when it forms predominantly or exclusively one stereoisomer when two or more are possible. • The E2 reaction is stereoselective because one stereoisomer is formed preferentially. Why? ...
1 Bite Angle Effects of Diphosphines in Carbonylation Reactions
... systematic studies using diphosphines was by Unruh [23] who used substituted dppf. Both rate and selectivity increase when the w-value of the ligands increase. There are two possible reasons: electrons preference for linear alkyl complex formation when the p-back-donation to the phosphine increases ...
... systematic studies using diphosphines was by Unruh [23] who used substituted dppf. Both rate and selectivity increase when the w-value of the ligands increase. There are two possible reasons: electrons preference for linear alkyl complex formation when the p-back-donation to the phosphine increases ...
Synthesis of first row transition metal carboxylate complexes by ring
... tetrahydrate with pyromellitic dianhydride in the presence of 2,2 -bipyridine in methanol gave a mononuclear nickel(II) complex (scheme 2). This complex is totally different from the one that have 1,10phenathroline. The 2,2 -bipyridine containing complex has non-coordinating carboxylate anions. Th ...
... tetrahydrate with pyromellitic dianhydride in the presence of 2,2 -bipyridine in methanol gave a mononuclear nickel(II) complex (scheme 2). This complex is totally different from the one that have 1,10phenathroline. The 2,2 -bipyridine containing complex has non-coordinating carboxylate anions. Th ...
Alkyl halide
... What product would you expect from a nucleophilic substitution reaction of (R)-1-bromo-1-phenylethane with cyanide ion, -C≡N as nucleophile? Show the stereochemistry of both reactant and product, assuming that inversion of configuration occurs. ...
... What product would you expect from a nucleophilic substitution reaction of (R)-1-bromo-1-phenylethane with cyanide ion, -C≡N as nucleophile? Show the stereochemistry of both reactant and product, assuming that inversion of configuration occurs. ...
Lab 9 - Academic Computer Center
... does not react with these solvents. Therefore, NaBH4 is the reagent of choice for reducing aldehydes and ketones. Lithium aluminum hydride, LiAlH4, is a stronger reducing agent than NaBH4, and LiAlH4 is used to reduce carboxylic acids, epoxides, esters, lactones, nitro groups, nitriles, azides, amid ...
... does not react with these solvents. Therefore, NaBH4 is the reagent of choice for reducing aldehydes and ketones. Lithium aluminum hydride, LiAlH4, is a stronger reducing agent than NaBH4, and LiAlH4 is used to reduce carboxylic acids, epoxides, esters, lactones, nitro groups, nitriles, azides, amid ...
Alcohols, Ethers and Epoxides Alcohols contain a hydroxy group (OH)
... equilibrium will react to counteract any disturbance to the equilibrium. One consequence of this is that removing a product from a reaction mixture as it is formed drives the equilibrium to the right, forming more product. Thus, the alkene, which usually has a lower boiling point than the starting a ...
... equilibrium will react to counteract any disturbance to the equilibrium. One consequence of this is that removing a product from a reaction mixture as it is formed drives the equilibrium to the right, forming more product. Thus, the alkene, which usually has a lower boiling point than the starting a ...
ORGANOHALIDES + Nucleophilic Reactions (SN1
... • R-X, alkyl halides are ELECTROPHILES (positive or electron-poor) • They react with NUCLEOPHILES/BASES (negative or electron-rich) • Either substitution – C-C-X becomes C-C-blah + X- ...
... • R-X, alkyl halides are ELECTROPHILES (positive or electron-poor) • They react with NUCLEOPHILES/BASES (negative or electron-rich) • Either substitution – C-C-X becomes C-C-blah + X- ...
Organic Chemistry Introduction
... Anhydrous ammonia (NH3) is a liquid below -33 ºC Alkali metals dissolve in liquid ammonia Provide a solution of e- in NH3 Alkynes are reduced to trans alkenes with sodium or lithium in liquid ammonia ...
... Anhydrous ammonia (NH3) is a liquid below -33 ºC Alkali metals dissolve in liquid ammonia Provide a solution of e- in NH3 Alkynes are reduced to trans alkenes with sodium or lithium in liquid ammonia ...
Reactions of Alcohols - John Carroll University
... • Ethers can be synthesized by the reaction of alkoxide ions with primary alkyl halides in what is known as the Williamson ether synthesis. • This is an SN2 displacement reaction and as such, works better with primary alkyl halides to facilitate back-side attack. • If a secondary or tertiary alkyl h ...
... • Ethers can be synthesized by the reaction of alkoxide ions with primary alkyl halides in what is known as the Williamson ether synthesis. • This is an SN2 displacement reaction and as such, works better with primary alkyl halides to facilitate back-side attack. • If a secondary or tertiary alkyl h ...
Common aldehydes and ketones
... • A compound containing a carbonyl group (C=O) is normally in rapid equilibrium with an enol tautomer, which contains a pair of doubly bonded carbon atoms adjacent to a hydroxyl (−OH) group, C=C-OH. The keto form predominates at equilibrium for most ketones. Nonetheless, the enol form is important f ...
... • A compound containing a carbonyl group (C=O) is normally in rapid equilibrium with an enol tautomer, which contains a pair of doubly bonded carbon atoms adjacent to a hydroxyl (−OH) group, C=C-OH. The keto form predominates at equilibrium for most ketones. Nonetheless, the enol form is important f ...
CHAPTER 21 PHENOLS AND ARYL HALIDES
... Aryl halides and vinylic halides are relatively unreactive toward nucleophilic substitution under conditions that give facile nucleophilic substitution with alkyl halides. Reason: (1) Phenyl cations are very unstable. (2) Halogen bonds of aryl (and vinylic) halides are shorter and stronger than tho ...
... Aryl halides and vinylic halides are relatively unreactive toward nucleophilic substitution under conditions that give facile nucleophilic substitution with alkyl halides. Reason: (1) Phenyl cations are very unstable. (2) Halogen bonds of aryl (and vinylic) halides are shorter and stronger than tho ...
3.8 Aldehydes and ketones
... Aldehydes and ketones can be reduced back to the primary or secondary alcohol. Reducing agent used is sodium tetrahydidoborate (III), NaBH4. The reaction(s) are complex so we use [H] in the equation. ...
... Aldehydes and ketones can be reduced back to the primary or secondary alcohol. Reducing agent used is sodium tetrahydidoborate (III), NaBH4. The reaction(s) are complex so we use [H] in the equation. ...
Chemistry Name Mr. Reger Review Guide – Ch. 9
... 13. Using the chemical equation below, answer the following questions for a reaction in which 10.0g of CaCl2 is combined with 10.0g of Na2CO3. __ CaCl2(aq) + __ Na2CO3(aq) __ NaCl(aq) + __ CaCO3(s) a) What is the limiting reagent? b) How much of the excess reagent is left after the reaction is com ...
... 13. Using the chemical equation below, answer the following questions for a reaction in which 10.0g of CaCl2 is combined with 10.0g of Na2CO3. __ CaCl2(aq) + __ Na2CO3(aq) __ NaCl(aq) + __ CaCO3(s) a) What is the limiting reagent? b) How much of the excess reagent is left after the reaction is com ...
RULE
... bromine atom of Br2)… as this E+ accepts those electrons (forming bond), the bond between the two bromine atoms must break Although the electrons could be left as a lone pair on bromine (generating a carbocation), the proximity of a Nu: and E+ facilitate their interaction and attachment of bromi ...
... bromine atom of Br2)… as this E+ accepts those electrons (forming bond), the bond between the two bromine atoms must break Although the electrons could be left as a lone pair on bromine (generating a carbocation), the proximity of a Nu: and E+ facilitate their interaction and attachment of bromi ...
An Efficient Method for Selective Deprotection of Trimethylsilyl
... C6H5CH=CHCHO Menthone 4-COOH-C6H4CHO Tetralone 2-Methylcyclohexanone Benzil ...
... C6H5CH=CHCHO Menthone 4-COOH-C6H4CHO Tetralone 2-Methylcyclohexanone Benzil ...
Lewis base-assisted Lewis acid-catalyzed selective
... Acid‐catalyzed dehydration of alcohols has been widely employed for the synthesis of alkenes. However, activated alcohols when employed as substrates in dehydration reactions are often plagued by the lack of alkene selectivity. In this work, the reaction system can be signif ...
... Acid‐catalyzed dehydration of alcohols has been widely employed for the synthesis of alkenes. However, activated alcohols when employed as substrates in dehydration reactions are often plagued by the lack of alkene selectivity. In this work, the reaction system can be signif ...
101. Alcohols as alkylating agents in heteroarene C H functionalization
... and propanol deliver the alkylated isoquinoline product in high yields (33 and 34, 95% and 96% yield). Steric bulk proximal to the alcohol functionality is tolerated, as exemplified by the presence of isopropyl, b-tetrahydropyran, b-aryl and b-adamantyl substituents (35–38, 87– 92% yield). The prese ...
... and propanol deliver the alkylated isoquinoline product in high yields (33 and 34, 95% and 96% yield). Steric bulk proximal to the alcohol functionality is tolerated, as exemplified by the presence of isopropyl, b-tetrahydropyran, b-aryl and b-adamantyl substituents (35–38, 87– 92% yield). The prese ...
Iron(II) Chloride–1,1′-Binaphthyl-2,2′-diamine
... bar was charged with FeCl2 (3.2 mg, 0.025 mmol), 1,1′-binaphthyl2,2′-diamine (BINAM) (14.2 mg, 0.05 mmol), dicumyl peroxide (DCP) (473.2 mg, 1.75 mmol) and indole (1) (58.6 mg, 0.5 mmol). The pressure tube was evacuated and back-filled with N2. Anhydrous EtOH (2 mL) was added and the mixture was sti ...
... bar was charged with FeCl2 (3.2 mg, 0.025 mmol), 1,1′-binaphthyl2,2′-diamine (BINAM) (14.2 mg, 0.05 mmol), dicumyl peroxide (DCP) (473.2 mg, 1.75 mmol) and indole (1) (58.6 mg, 0.5 mmol). The pressure tube was evacuated and back-filled with N2. Anhydrous EtOH (2 mL) was added and the mixture was sti ...
Derivatization of polar compounds for GC - Sigma
... • Non-protic solvents •Can be used to facilitate the derivatization reaction • Common solvents: ACN, pyridine, DMF, DMSO, THF •Use the highest purity possible • Be aware of any added preservatives •In some cases, the derivatization reagent can act as the solvent • Excess may have to be removed prior ...
... • Non-protic solvents •Can be used to facilitate the derivatization reaction • Common solvents: ACN, pyridine, DMF, DMSO, THF •Use the highest purity possible • Be aware of any added preservatives •In some cases, the derivatization reagent can act as the solvent • Excess may have to be removed prior ...
Stille reaction
The Stille reaction, or the Migita-Kosugi-Stille coupling, is a chemical reaction widely used in organic synthesis which involves the coupling of an organotin compound (also known as organostannanes) with a variety of organic electrophiles via palladium-catalyzed coupling reaction.The R1 group attached to the trialkyltin is normally sp2-hybridized, including alkenes, and aryl groups; however, conditions have been devised to incorporate both sp3-hybridized groups, such as allylic and benzylic substituents, and sp-hybridized alkynes. These organostannanes are also stable to both air and moisture, and many of these reagents are either commercially available or can be synthesized from literature precedent. However, these tin reagents tend to be highly toxic. X is typically a halide, such as Cl, Br, I, yet pseudohalides such as triflates and sulfonates and phosphates can also be used.The groundwork for the Stille reaction was laid by Colin Eaborn, Toshihiko Migita, and Masanori Kosugi in 1976 and 1977, who explored numerous palladium catalyzed couplings involving organotin reagents. John Stille and David Milstein developed a much milder and more broadly applicable procedure in 1978. Stille’s work on this area might have earned him a share of the 2010 Nobel Prize, which was awarded to Richard Heck, Ei-ichi Negishi, and Akira Suzuki for their work on the Heck, Negishi, and Suzuki coupling reactions. However, Stille died in the plane crash of United Airlines Flight 232 in 1989.Several reviews have been published on the Stille reaction.