Brominations and Alkene Synthesis CHM 233 Review
... look from here, looks like this • ANTI addition, bromines add to opposite sides of the C=C double bond (top and bottom) • note new type of structure for indicating stereochemistry on rings, trans- in this case • NOTE, because of bromonium ion intermediate (no "free" carbocation) there are no rearran ...
... look from here, looks like this • ANTI addition, bromines add to opposite sides of the C=C double bond (top and bottom) • note new type of structure for indicating stereochemistry on rings, trans- in this case • NOTE, because of bromonium ion intermediate (no "free" carbocation) there are no rearran ...
Alkyl and Aryl Halides
... present in high concentrations favor SN2 reactions. • Weak nucleophiles, such as H2O and ROH favor SN1 reactions by decreasing the rate of any competing SN2 reaction. • Let us compare the substitution products formed when the 2° alkyl halide A is treated with either the strong nucleophile HO¯ or the ...
... present in high concentrations favor SN2 reactions. • Weak nucleophiles, such as H2O and ROH favor SN1 reactions by decreasing the rate of any competing SN2 reaction. • Let us compare the substitution products formed when the 2° alkyl halide A is treated with either the strong nucleophile HO¯ or the ...
Development of Lewis Acid Mediated Stereoselective Synthesis of
... strain, which has been estimated by molecular orbital calculations to be 44-48 kcal/mol.18 This ring strain, the reactive π-bond and the nitrogen lone pair electrons make the 2H-azirines highly reactive and allow for their participation in a variety of reactions. The majority of these, such as nucle ...
... strain, which has been estimated by molecular orbital calculations to be 44-48 kcal/mol.18 This ring strain, the reactive π-bond and the nitrogen lone pair electrons make the 2H-azirines highly reactive and allow for their participation in a variety of reactions. The majority of these, such as nucle ...
Synthesis_of_Organometallic_Compounds
... complexes has been extensively explored. • less application in organic synthesis than palladium compounds, probably because their chemistry is more complicated. ...
... complexes has been extensively explored. • less application in organic synthesis than palladium compounds, probably because their chemistry is more complicated. ...
CHM 222 - Jefferson State Community College
... Demonstrate an understanding of reactions involving aldehydes, ketones, carboxylic acids and their derivatives including nomenclature, synthesis and mechanisms. 1. Name and draw aldehydes, ketones, carboxylic acids and their derivatives. 2. Propose a synthesis for each type of compound listed above. ...
... Demonstrate an understanding of reactions involving aldehydes, ketones, carboxylic acids and their derivatives including nomenclature, synthesis and mechanisms. 1. Name and draw aldehydes, ketones, carboxylic acids and their derivatives. 2. Propose a synthesis for each type of compound listed above. ...
Nucleophilic Addition: The Grignard reagent
... Nucleophilic substitutions at secondary and tertiary sites are difficult; often elimination reactions occur instead. Thus, substitution reactions aren’t a particularly good method for synthesizing secondary and tertiary alcohols. On the other hand, reacting Grignard reagents, carbon based nucleophil ...
... Nucleophilic substitutions at secondary and tertiary sites are difficult; often elimination reactions occur instead. Thus, substitution reactions aren’t a particularly good method for synthesizing secondary and tertiary alcohols. On the other hand, reacting Grignard reagents, carbon based nucleophil ...
(a) Draw a primary, a secondary, and a tertiary alcohol for the
... Describe the different types of reactions occurring, and give reasons why they are classified as that type. Identify any specific conditions that are needed for the reactions to occur. When propan-1-ol reacts with HCl, a substitution reaction occurs; in this reaction the Cl from HCl replaces the –OH ...
... Describe the different types of reactions occurring, and give reasons why they are classified as that type. Identify any specific conditions that are needed for the reactions to occur. When propan-1-ol reacts with HCl, a substitution reaction occurs; in this reaction the Cl from HCl replaces the –OH ...
Discussion Sheet 11
... Oxidation of alcohols produce electrophiles that can be used in a future C-C bond forming step Transformation of an alcohol into an alkylhalide, followed by Grignard formation, allows an alcohol to be made into a nucleophile ...
... Oxidation of alcohols produce electrophiles that can be used in a future C-C bond forming step Transformation of an alcohol into an alkylhalide, followed by Grignard formation, allows an alcohol to be made into a nucleophile ...
Chapter 10: Alkyl Halides
... Allylic Bromination with NBS is analogous to the radical reaction with an alkane, a halogen and uv light (Ch. 5). The NBS can be thought of as producing a Br radical. The Br radical removes a hydrogen, leaving an allylic radical and forming HBr. This allylic radical reacts with Br2 (which is formed ...
... Allylic Bromination with NBS is analogous to the radical reaction with an alkane, a halogen and uv light (Ch. 5). The NBS can be thought of as producing a Br radical. The Br radical removes a hydrogen, leaving an allylic radical and forming HBr. This allylic radical reacts with Br2 (which is formed ...
Carbonyl The carbonyl function, C=O, exists in a number of organic
... bond such that the carbon atom has positive character and the oxygen atom has negative character. The positive carbon atom is electrophilic and is responsible for much of the observed chemistry, such as acidity of alpha hydrogens and nucleophic reactions at the carbonyl. If florine atoms are located ...
... bond such that the carbon atom has positive character and the oxygen atom has negative character. The positive carbon atom is electrophilic and is responsible for much of the observed chemistry, such as acidity of alpha hydrogens and nucleophic reactions at the carbonyl. If florine atoms are located ...
Chem 30CL - Lecture 1c - UCLA Chemistry and Biochemistry
... • In 1976, E. J. Corey and D. Enders developed the SAMP and RAMP approach that uses cyclic amino acid derivatives ((S)-proline for SAMP, (R)-glutamic acid for RAMP) and hydrazones to control the stereochemistry of the product. • Below is an example for the use of SAMP in an asymmetric ...
... • In 1976, E. J. Corey and D. Enders developed the SAMP and RAMP approach that uses cyclic amino acid derivatives ((S)-proline for SAMP, (R)-glutamic acid for RAMP) and hydrazones to control the stereochemistry of the product. • Below is an example for the use of SAMP in an asymmetric ...
New L-Serine Derivative Ligands as Cocatalysts for Diels
... of a vast variety of compounds of chemical, biological, and pharmaceutical interest [1, 2]. The most efficient and widely used method for the preparation of bicyclic compounds is the Diels-Alder reaction. Generally, activation by an electronwithdrawing group and a Lewis acid is required in order to ...
... of a vast variety of compounds of chemical, biological, and pharmaceutical interest [1, 2]. The most efficient and widely used method for the preparation of bicyclic compounds is the Diels-Alder reaction. Generally, activation by an electronwithdrawing group and a Lewis acid is required in order to ...
ALDOL CONDENSATION
... three resonance structures that can be drawn for this species, two of which have enolate ions. This nucleophile reacts with the electrophilic alkene 3 to form 4 in a conjugate addition reaction. Proton abstraction from protonated base (or solvent) by the enolate 4 to 5 is the final step. The co ...
... three resonance structures that can be drawn for this species, two of which have enolate ions. This nucleophile reacts with the electrophilic alkene 3 to form 4 in a conjugate addition reaction. Proton abstraction from protonated base (or solvent) by the enolate 4 to 5 is the final step. The co ...
Remodeling of the natural product fumagillol
... Further optimization using La(OTf)3 and Zn(OTf)2 catalysts was next pursued. The transformations were robust and did not require inert atmosphere, nor special precautions for anhydrous solvent. Other nonpolar solvents provided similar regioselectivity, though toluene proved to be optimal, in which c ...
... Further optimization using La(OTf)3 and Zn(OTf)2 catalysts was next pursued. The transformations were robust and did not require inert atmosphere, nor special precautions for anhydrous solvent. Other nonpolar solvents provided similar regioselectivity, though toluene proved to be optimal, in which c ...
A Biocatalytic Henry Reaction-The Hydroxynitrile Lyase from Hevea
... evolve only a few decades ago. In these studies various nonenzymatic catalysts have been utilized.[7] Our results represent the first example of a biocatalytic asymmetric Henry reaction. The HbHNL-catalyzed addition of nitromethane to benzaldehyde was carried out under standard conditions after adju ...
... evolve only a few decades ago. In these studies various nonenzymatic catalysts have been utilized.[7] Our results represent the first example of a biocatalytic asymmetric Henry reaction. The HbHNL-catalyzed addition of nitromethane to benzaldehyde was carried out under standard conditions after adju ...
Date - Chaminade University`s syllabus repository
... Identify and classify organic molecules according to their functional groups Carry out functional group inter-conversions of the classes of compounds studied Illustrate the mechanism of each of the functional group inter-conversions identifying intermediates and transition states where appropr ...
... Identify and classify organic molecules according to their functional groups Carry out functional group inter-conversions of the classes of compounds studied Illustrate the mechanism of each of the functional group inter-conversions identifying intermediates and transition states where appropr ...
Acid-Catalyzed Dehydration of Alcohols
... One of the easiest organic chemical syntheses is the dehydration of an alcohol using sulfuric acid as a catalyst to produce an alkene(s). The alcohols are first protonated in the acid to form the oxonium ion that dehydrates at elevated temperatures to yield a carbocation. In the second step in the r ...
... One of the easiest organic chemical syntheses is the dehydration of an alcohol using sulfuric acid as a catalyst to produce an alkene(s). The alcohols are first protonated in the acid to form the oxonium ion that dehydrates at elevated temperatures to yield a carbocation. In the second step in the r ...
The aim of the work
... our investigation the products can be formed in parallel from one and the same intermediate compound. In this case the reaction between deprotonated pyranone and protonated aldol A is not regiospecific and intermediate lakes part in substitution reaction only. Such mechanism can explain why the yiel ...
... our investigation the products can be formed in parallel from one and the same intermediate compound. In this case the reaction between deprotonated pyranone and protonated aldol A is not regiospecific and intermediate lakes part in substitution reaction only. Such mechanism can explain why the yiel ...
aciee-2004-43-5442-palomo
... date, a few other zinc complexes bearing amino alcohol ligands[15] and macrocyclic thioaza ligands[16] have been described for the Henry reaction. Because the results are still poor, future developments in the area can be expected. In an important recent report, Evans et al.[17] have formulated that ...
... date, a few other zinc complexes bearing amino alcohol ligands[15] and macrocyclic thioaza ligands[16] have been described for the Henry reaction. Because the results are still poor, future developments in the area can be expected. In an important recent report, Evans et al.[17] have formulated that ...
Alcohols from Alkenes: Oxymercuration–Demercuration
... Alcohols from Alkenes: Oxymercuration–Demercuration ...
... Alcohols from Alkenes: Oxymercuration–Demercuration ...
Elimination Reactions
... Geometry of E2 Elimination Like the SN2 substitution (which requires backside attack), the E2 elimination reaction has a geometric preference for an anti-coplanar orientation of the H-C-C-X bonds. In some cases, this may result in a stereospecific reaction, where one stereoisomer of the halide resu ...
... Geometry of E2 Elimination Like the SN2 substitution (which requires backside attack), the E2 elimination reaction has a geometric preference for an anti-coplanar orientation of the H-C-C-X bonds. In some cases, this may result in a stereospecific reaction, where one stereoisomer of the halide resu ...
Topic 16 Test - A
... How many structural isomers, which are aldehydes, have the molecular formula C5H10O? A ...
... How many structural isomers, which are aldehydes, have the molecular formula C5H10O? A ...
Document
... • We Know 2° Carbocations More Stable Than 1° • Major Product Formed From More Stable C+ Intermediate • Means TS in 2° Carbocation Pathway Lower in Energy • Lower Energy of Activation • Activation Energies in 1° Carbocation Pathways Much Larger ...
... • We Know 2° Carbocations More Stable Than 1° • Major Product Formed From More Stable C+ Intermediate • Means TS in 2° Carbocation Pathway Lower in Energy • Lower Energy of Activation • Activation Energies in 1° Carbocation Pathways Much Larger ...
Diels–Alder reaction
.png?width=300)
The Diels–Alder reaction is an organic chemical reaction (specifically, a [4+2] cycloaddition) between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene system. It was first described by Otto Paul Hermann Diels and Kurt Alder in 1928, for which work they were awarded the Nobel Prize in Chemistry in 1950. The Diels–Alder reaction is particularly useful in synthetic organic chemistry as a reliable method for forming 6-membered systems with good control over regio- and stereochemical properties. The underlying concept has also been applied to other π-systems, such as carbonyls and imines, to furnish the corresponding heterocycles, known as the hetero-Diels–Alder reaction. Diels–Alder reactions can be reversible under certain conditions; the reverse reaction is known as the retro-Diels–Alder reaction.