GRIGNARD REAGENTS
... carbonyl carbon to the oxygen atom by by sp2 (C) –2p (O) overlap. The π bond is formed by 2p(C) – 2p(O) overlap. Carbonyl groups are flat. The π electrons are above and below the trigonal plane formed by the sp2 orbitals of the carbonyl carbon. ...
... carbonyl carbon to the oxygen atom by by sp2 (C) –2p (O) overlap. The π bond is formed by 2p(C) – 2p(O) overlap. Carbonyl groups are flat. The π electrons are above and below the trigonal plane formed by the sp2 orbitals of the carbonyl carbon. ...
Electophilic Aromatic Substituion
... • In the first step the electrons act as a nucleophile toward Br2 (in a complex with FeBr3) • This forms a cationic addition intermediate from benzene and a bromine cation • The intermediate is not aromatic and therefore ...
... • In the first step the electrons act as a nucleophile toward Br2 (in a complex with FeBr3) • This forms a cationic addition intermediate from benzene and a bromine cation • The intermediate is not aromatic and therefore ...
Group 13 Compounds - University of Ottawa
... There are three available oxidation states for the group 13 compounds, represented by the basic formulae: R3M – where M(III) is any metal in the group. This is by far the most common organometallic species for group 13. R2M-MR2 – M(II) with a homonuclear bond. Not common. RM: – M(I) accessible due t ...
... There are three available oxidation states for the group 13 compounds, represented by the basic formulae: R3M – where M(III) is any metal in the group. This is by far the most common organometallic species for group 13. R2M-MR2 – M(II) with a homonuclear bond. Not common. RM: – M(I) accessible due t ...
Alcohols
... The reactivity of NaBH4 is much lower than a free hydride ion, and NaBH4 can be used in protic solvents such as ethanol. The mechanism of a sodium borohydride reduction involves: • Donation of H- to the carbonyl carbon • Simultaneous protonation of the carbonyl oxygen by a solvent molecule • Combin ...
... The reactivity of NaBH4 is much lower than a free hydride ion, and NaBH4 can be used in protic solvents such as ethanol. The mechanism of a sodium borohydride reduction involves: • Donation of H- to the carbonyl carbon • Simultaneous protonation of the carbonyl oxygen by a solvent molecule • Combin ...
Practice Problem
... • Reaction distinction is more selective with bromine than chlorine • Reaction with Br. is much less exergonic • T.Sbromination resembles the alkyl radical more closely than does T.Schlorination ...
... • Reaction distinction is more selective with bromine than chlorine • Reaction with Br. is much less exergonic • T.Sbromination resembles the alkyl radical more closely than does T.Schlorination ...
EXP-6
... 1. Tollen’s reagent consists of two solutions: solution A and B. Solution A contains 5% aqueous silver nitrate, solution B contain 10% aq. KOH. 2. Prepare Tollen’s reagent by mixing solution A (2.5 g of silver nitrate in 43 ml of distilled water) and solution B (3g of potassium hydroxide in 42 ml of ...
... 1. Tollen’s reagent consists of two solutions: solution A and B. Solution A contains 5% aqueous silver nitrate, solution B contain 10% aq. KOH. 2. Prepare Tollen’s reagent by mixing solution A (2.5 g of silver nitrate in 43 ml of distilled water) and solution B (3g of potassium hydroxide in 42 ml of ...
Step 1
... positive inductive effect of alkyl groups). One might expect using the same trend that tertiary amine would be the strongest amine base but the trend does not hold. The tertiary amines and corresponding ammonium salts are less soluble in water and this makes them less strong bases than the secon ...
... positive inductive effect of alkyl groups). One might expect using the same trend that tertiary amine would be the strongest amine base but the trend does not hold. The tertiary amines and corresponding ammonium salts are less soluble in water and this makes them less strong bases than the secon ...
Arginine- or Lysine-catalyzed Michael Addition of Nitromethane to α
... addition of nitroalkanes provide a variety of key building blocks for various compounds, such as an amine, ketone, alkane, and alkene.4 The most widely studied amino acid as a catalyst is proline. The reaction mechanisms of the proline-catalyzed reactions with carbonyl compounds are mainly involved ...
... addition of nitroalkanes provide a variety of key building blocks for various compounds, such as an amine, ketone, alkane, and alkene.4 The most widely studied amino acid as a catalyst is proline. The reaction mechanisms of the proline-catalyzed reactions with carbonyl compounds are mainly involved ...
Working with Hazardous Chemicals
... as nucleophilic catalysts in group transfer reactions.5 The esterification proceeds without the need of a preformed, activated carboxylic acid derivative, at room temperature, under nonacidic, mildly basic conditions. In addition to dichloromethane other aprotic solvents of comparable polarity such ...
... as nucleophilic catalysts in group transfer reactions.5 The esterification proceeds without the need of a preformed, activated carboxylic acid derivative, at room temperature, under nonacidic, mildly basic conditions. In addition to dichloromethane other aprotic solvents of comparable polarity such ...
O-isopropylideneadenosine (1)
... To a solution of exo-1 (400 mg, 1.8 mmol) in anhydrous THF (18 mL), under argon atmosphere, were added UHP (3.4 g, 36 mmol) and Amberlyst-15 (400 mg, 100% weight with respect to 1). The heterogeneous mixture was stirred for 24 h at room temperature. Then, it was throughly filtered over celite with p ...
... To a solution of exo-1 (400 mg, 1.8 mmol) in anhydrous THF (18 mL), under argon atmosphere, were added UHP (3.4 g, 36 mmol) and Amberlyst-15 (400 mg, 100% weight with respect to 1). The heterogeneous mixture was stirred for 24 h at room temperature. Then, it was throughly filtered over celite with p ...
Chemistry (9701/11)
... International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at www.cie.org.uk after the live examination series. Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessmen ...
... International Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at www.cie.org.uk after the live examination series. Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessmen ...
Microwave-Enhanced Sulphated Zirconia and SZ/MCM
... When the aminolysis reaction takes place mainly through microwave assistance, the yields are typically lower than 5 %, although entries 11, 13, 15, 17 and 19 gave yields of 11, 12, 11, 36 and 9 %, respectively. Entries 1, 2, 4, 6, 7, 8, 9, 10, 14 and 18 did not afford any reaction products. The appl ...
... When the aminolysis reaction takes place mainly through microwave assistance, the yields are typically lower than 5 %, although entries 11, 13, 15, 17 and 19 gave yields of 11, 12, 11, 36 and 9 %, respectively. Entries 1, 2, 4, 6, 7, 8, 9, 10, 14 and 18 did not afford any reaction products. The appl ...
Bimolecular reactions of the chromium
... ligand. This is of particular interest if the free ligand is unstable and difficult to handle under the conditions typical of synthetic chemistry. Benzyne (18-didehydrobenzene) and other arynes are very reactive intermediates3 which have to be prepared in situ during a chemical syntheeis.’ However, ...
... ligand. This is of particular interest if the free ligand is unstable and difficult to handle under the conditions typical of synthetic chemistry. Benzyne (18-didehydrobenzene) and other arynes are very reactive intermediates3 which have to be prepared in situ during a chemical syntheeis.’ However, ...
Article - Sociedade Brasileira de Química
... two ketones such as 9-fluorenone or 4-phenyl-2-butanone versus acetophenone; here, it was found that 9-fluorenone and 4-phenyl-2-butanone were reduced in high chemoselectivity (Table 4). Regioselective 1,2-reduction of α,β-unsaturated aldehydes and ketones is an easy way to obtain allylic alcohols w ...
... two ketones such as 9-fluorenone or 4-phenyl-2-butanone versus acetophenone; here, it was found that 9-fluorenone and 4-phenyl-2-butanone were reduced in high chemoselectivity (Table 4). Regioselective 1,2-reduction of α,β-unsaturated aldehydes and ketones is an easy way to obtain allylic alcohols w ...
AlCl3 in modern chemistry of polyfluoroarenes
... continued. Chemistry of polyfluoroarenes is one of comparatively new fields in which possibility of using AlCl3 has been demonstrated. This report presents a data review of AlCl3 application in the chemistry of polyfluoroarenes beginning since 1995y. As substrates or reagents there are given fluorin ...
... continued. Chemistry of polyfluoroarenes is one of comparatively new fields in which possibility of using AlCl3 has been demonstrated. This report presents a data review of AlCl3 application in the chemistry of polyfluoroarenes beginning since 1995y. As substrates or reagents there are given fluorin ...
TGA with Evolved Gas Analysis
... Decomposition of BHET BHET (bis-hydroxyethyl terephthalate) is an intermediate used in the production of PET. It is produced by the esterification of terephthalic acid with ethylene glycol. Two weight loss steps were observed on heating BHET in the TGA. A direct comparison of the IR spectrum measure ...
... Decomposition of BHET BHET (bis-hydroxyethyl terephthalate) is an intermediate used in the production of PET. It is produced by the esterification of terephthalic acid with ethylene glycol. Two weight loss steps were observed on heating BHET in the TGA. A direct comparison of the IR spectrum measure ...
Experiment # 8 Synthesis and Reactivity of tert
... it. Open the stopcock immediately to release excess pressure, pointing the funnel towards the back of the fumehood. Shake the funnel and vent at regular intervals. Place the funnel in a ring stand and allow the two layers to separate. Drain the lower aqueous layer into a 250 mL Erlenmeyer flask (lab ...
... it. Open the stopcock immediately to release excess pressure, pointing the funnel towards the back of the fumehood. Shake the funnel and vent at regular intervals. Place the funnel in a ring stand and allow the two layers to separate. Drain the lower aqueous layer into a 250 mL Erlenmeyer flask (lab ...
Fluorine notes- EFFECT OF POLYFLUOROALKYL GROUPS IN
... Reaction of polyfluoroalkylchlorosulphites with cinnamic alcohol had been carried in two stages. During first stage reagents (cinnamic alcohol, potassium carbonate and polyfluoroalkylchlorosulphite) were mixed in chloroform at –10÷–5 °C, while there was the appearance of color–the solution became or ...
... Reaction of polyfluoroalkylchlorosulphites with cinnamic alcohol had been carried in two stages. During first stage reagents (cinnamic alcohol, potassium carbonate and polyfluoroalkylchlorosulphite) were mixed in chloroform at –10÷–5 °C, while there was the appearance of color–the solution became or ...
Two-Electron Reduction of a Vanadium(V) Nitride by CO to Release
... 150.6(1)°, on par with other isocyanate complexes.6 With 1-V(NCO) in hand, attention turned to probing the redox chemistry of the complex. When treated with 0.5% Na/Hg in the same manner as had been done for 1-Nb(NCO), 1-V(NCO) undergoes cyanate dissociation to give 1-V and sodium cyanate (Scheme 1B ...
... 150.6(1)°, on par with other isocyanate complexes.6 With 1-V(NCO) in hand, attention turned to probing the redox chemistry of the complex. When treated with 0.5% Na/Hg in the same manner as had been done for 1-Nb(NCO), 1-V(NCO) undergoes cyanate dissociation to give 1-V and sodium cyanate (Scheme 1B ...
Document
... H. Often, a CO bond or CC bond is reduced to a single bond by reduction. A reduction that transforms double CC or CO bonds to single bonds may also be classified as an addition reaction. Aldehydes, ketones, and carboxylic acids can be reduced to become alcohols. Alkenes and alkynes can be reduce ...
... H. Often, a CO bond or CC bond is reduced to a single bond by reduction. A reduction that transforms double CC or CO bonds to single bonds may also be classified as an addition reaction. Aldehydes, ketones, and carboxylic acids can be reduced to become alcohols. Alkenes and alkynes can be reduce ...
Concerted Acid-Base Catalysis
... Reactants must come together with the proper spatial relationship for a reaction to occur Proximity effects (minor) are most readily observed by comparing equivalent inter- and intramolecular reactions Intramolecular reactions are typically 10-100 fold more rapid ...
... Reactants must come together with the proper spatial relationship for a reaction to occur Proximity effects (minor) are most readily observed by comparing equivalent inter- and intramolecular reactions Intramolecular reactions are typically 10-100 fold more rapid ...
$doc.title
... Uses of the Wing Reac3on • Can be used for monosubs3tuted, disubs3tuted, and trisubs3tuted alkenes but not tetrasubs3tuted alkenes The reac3on yields a pure alkene of known structure • For comparison, addi3 ...
... Uses of the Wing Reac3on • Can be used for monosubs3tuted, disubs3tuted, and trisubs3tuted alkenes but not tetrasubs3tuted alkenes The reac3on yields a pure alkene of known structure • For comparison, addi3 ...
Document
... • Usually Dissolved in Solvent (CH3CO2H, CH2Cl2) • Can be Bubbled Through Solution as a Gas • Addition of HCl not Generally Useful (Works w/ Silica Gel) ...
... • Usually Dissolved in Solvent (CH3CO2H, CH2Cl2) • Can be Bubbled Through Solution as a Gas • Addition of HCl not Generally Useful (Works w/ Silica Gel) ...
Synthesis_of_Organometallic_Compounds
... A coordinatively unsaturated 16eruthenium(0) complex • Reduction of RuCl2(CO)2(PtBu2Me)2 with magnesium affords an isolable 16e ruthenium(0) complex Ru(CO)2(PtBu2Me)2. • Highly reactive toward hydrogen, acetylenes and phosphines to give coordinatively saturated complexes. ...
... A coordinatively unsaturated 16eruthenium(0) complex • Reduction of RuCl2(CO)2(PtBu2Me)2 with magnesium affords an isolable 16e ruthenium(0) complex Ru(CO)2(PtBu2Me)2. • Highly reactive toward hydrogen, acetylenes and phosphines to give coordinatively saturated complexes. ...
Document
... The reagents LiAlH4, ZnH,, MgH,, complex A and complex C are similar in their selectivity towards camphor giving 90-94s endo attack. The syn C-7 methyl group severely blocks exo attack and the results are in accordance with this. Complex B and especially its magnesium analogue, complex D, give less ...
... The reagents LiAlH4, ZnH,, MgH,, complex A and complex C are similar in their selectivity towards camphor giving 90-94s endo attack. The syn C-7 methyl group severely blocks exo attack and the results are in accordance with this. Complex B and especially its magnesium analogue, complex D, give less ...
Wolff–Kishner reduction
The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step. As such, there is no obvious retron for this reaction. Originally reported by Nikolai Kischner in 1911 and Ludwig Wolff in 1912, it has been applied to the total synthesis of scopadulcic acid B, aspidospermidine and dysidiolide.In general, the reaction mechanism first involves the in situ generation of a hydrazone by condensation of hydrazine with the ketone or aldehyde substrate. Sometimes it is however advantageous to use a pre-formed hydrazone as substrate (see modifications). The hydrazone is deprotonated by alkoxide base followed by a concerted, rate-determining step in which a diimide anion is formed. Collapse of this alkyldiimde with loss of N2 leads to formation of an alkylanion which can be protonated by solvent to give the desired product.Because the Wolff–Kishner reduction requires highly basic conditions, it is unsuitable for base-sensitive substrates. However, this method can be superior over the related Clemmensen reduction for acid-sensitive compounds such as pyrroles and for high-molecular weight compounds.