Benzyne Mechanism
... Phenols and phenoxides are highly reactive. Only a weak catalyst (HF) required for FriedelCrafts reaction. Tribromination occurs without catalyst. Even reacts with CO2. O ...
... Phenols and phenoxides are highly reactive. Only a weak catalyst (HF) required for FriedelCrafts reaction. Tribromination occurs without catalyst. Even reacts with CO2. O ...
chapt13
... leaving group. An intermediate is theorized in which the nucleophile is partially bonded to the molecule, while the leaving group is partially dissociated. The nucleophile donates two electrons and the leaving group takes two electrons ...
... leaving group. An intermediate is theorized in which the nucleophile is partially bonded to the molecule, while the leaving group is partially dissociated. The nucleophile donates two electrons and the leaving group takes two electrons ...
Nucleophilicity and Basicity Factors in Organic Reactions
... Electrophile: An electron deficient atom, ion or molecule that has an affinity for an electron pair, and will bond to a base or nucleophile. Nucleophile: An atom, ion or molecule that has an electron pair that may be donated in bonding to an electrophile (or Lewis acid). ...
... Electrophile: An electron deficient atom, ion or molecule that has an affinity for an electron pair, and will bond to a base or nucleophile. Nucleophile: An atom, ion or molecule that has an electron pair that may be donated in bonding to an electrophile (or Lewis acid). ...
Alkyl and Aryl Halides
... • Methyl and 1° alkyl halides undergo SN2 reactions with ease. • 2° Alkyl halides react more slowly. • 3° Alkyl halides do not undergo SN2 reactions. This order of reactivity can be explained by steric effects. Steric hindrance caused by bulky R groups makes nucleophilic attack from the backside mo ...
... • Methyl and 1° alkyl halides undergo SN2 reactions with ease. • 2° Alkyl halides react more slowly. • 3° Alkyl halides do not undergo SN2 reactions. This order of reactivity can be explained by steric effects. Steric hindrance caused by bulky R groups makes nucleophilic attack from the backside mo ...
Chapter16McMurryPPP
... Sulfonic acids are useful as intermediates Heating with NaOH at 300 ºC followed by neutralization with acid replaces the SO3H group with an OH Example is the synthesis of p-cresol ...
... Sulfonic acids are useful as intermediates Heating with NaOH at 300 ºC followed by neutralization with acid replaces the SO3H group with an OH Example is the synthesis of p-cresol ...
Orbitals - drjosephryan.com
... 14.7 Nucleophilic Addition of Amines: Imine and Enamine Formation Primary amines, RNH2, add to aldehydes and ketones to yield imines, R2C=NR Secondary amines, R2NH, add similarly to yield enamines, R2N-CR=CR2 ...
... 14.7 Nucleophilic Addition of Amines: Imine and Enamine Formation Primary amines, RNH2, add to aldehydes and ketones to yield imines, R2C=NR Secondary amines, R2NH, add similarly to yield enamines, R2N-CR=CR2 ...
Chemdraw B&W
... • Heat cyclic dicarboxylic acids that can form five- or sixmembered rings • Acyclic anhydrides are not generally formed this way they are usually made from acid chlorides and carboxylic acids ...
... • Heat cyclic dicarboxylic acids that can form five- or sixmembered rings • Acyclic anhydrides are not generally formed this way they are usually made from acid chlorides and carboxylic acids ...
Overview of the Reactions of Carbonyl Compounds
... • Nu- approaches 45° to the plane of C=O and adds to the Carbonyl Carbon • A tetrahedral alkoxide ion intermediate is produced and ultimately protonated ...
... • Nu- approaches 45° to the plane of C=O and adds to the Carbonyl Carbon • A tetrahedral alkoxide ion intermediate is produced and ultimately protonated ...
EXPERIMENT 6 (Organic Chemistry II) Pahlavan/Cherif
... In the case of ketones there are two carbon atoms bonded to the carbonyl carbon and no hydrogens. In the case of aldehydes there is at least one hydrogen bonded to the carbonyl carbon, the other attachment may be to a carbon or a hydrogen. In all cases the carbon(s) that are attached to the carbonyl ...
... In the case of ketones there are two carbon atoms bonded to the carbonyl carbon and no hydrogens. In the case of aldehydes there is at least one hydrogen bonded to the carbonyl carbon, the other attachment may be to a carbon or a hydrogen. In all cases the carbon(s) that are attached to the carbonyl ...
39 ESTERIFICATION: PREPARATION OF BENZYL ACETATE
... theoretical yield increases to 85%. When one is tripled, it goes to 90%. But note that in the example cited, the boiling point of the relatively nonpolar ester is only about 8°C higher than the boiling points of the polar acetic acid and 1-butanol, so a difficult separation problem exists if either ...
... theoretical yield increases to 85%. When one is tripled, it goes to 90%. But note that in the example cited, the boiling point of the relatively nonpolar ester is only about 8°C higher than the boiling points of the polar acetic acid and 1-butanol, so a difficult separation problem exists if either ...
Chapter 19. Aldehydes and Ketones
... 19.9 Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction ...
... 19.9 Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction ...
Alicyclic esters of phosphoric acids
... 30 acid per mole of bicycloheptadiene. This limitation is the cycloalkane, cyclohexane. not critical, however, and a larger or smaller amount of The desired product may be obtained from the reaction the bicycloheptadiene may be employed. It is preferable mixture by methods known in the art. For exam ...
... 30 acid per mole of bicycloheptadiene. This limitation is the cycloalkane, cyclohexane. not critical, however, and a larger or smaller amount of The desired product may be obtained from the reaction the bicycloheptadiene may be employed. It is preferable mixture by methods known in the art. For exam ...
File - TGHS Level 3 Chemistry
... Soaps are the sodium salts of fatty acids (long chain acids). These salts are soluble in water as they are ionised, but they have a carbon chain end that is soluble in fats and oils. This allows them to dissolve and break down dirt. Sodium laurate is the name of the soap molecule made from coconut o ...
... Soaps are the sodium salts of fatty acids (long chain acids). These salts are soluble in water as they are ionised, but they have a carbon chain end that is soluble in fats and oils. This allows them to dissolve and break down dirt. Sodium laurate is the name of the soap molecule made from coconut o ...
HL ISSN: 2231 – 3087(print) / 2230 – 9632 (Online)
... 2-(2-Methoxyaryl)-1-arylethanone derivativevi when subjected to hydrogenation by passing hydrogen gas in presence of palladium on charcoal in ethanol containing hydrochloric acid forming 2-arylbenzofuran. In an alternative approach, 2-(2-Methoxyaryl)-1-arylethanone derivative are cyclised using HI i ...
... 2-(2-Methoxyaryl)-1-arylethanone derivativevi when subjected to hydrogenation by passing hydrogen gas in presence of palladium on charcoal in ethanol containing hydrochloric acid forming 2-arylbenzofuran. In an alternative approach, 2-(2-Methoxyaryl)-1-arylethanone derivative are cyclised using HI i ...
Chapter 21: Carboxylic Acid Derivatives
... Nucleophilic Acyl Substitution Reactions of Carboxylic Acids ...
... Nucleophilic Acyl Substitution Reactions of Carboxylic Acids ...
organic chemistry i
... Homolytic and heterolytic chemistry Relative rates of competing reactions Structure. The functional group Classification Nomenclature Physical properties Preparation o from alcohols o halogenation of hydrocarbons o addition of hydrogen halide o addition of halogens to alkenes o addition of halogens ...
... Homolytic and heterolytic chemistry Relative rates of competing reactions Structure. The functional group Classification Nomenclature Physical properties Preparation o from alcohols o halogenation of hydrocarbons o addition of hydrogen halide o addition of halogens to alkenes o addition of halogens ...
Chapter_Sixteen_lecture
... Oxidation of Aldehydes Produces a carboxylic acid 1. Aldehyde oxidation results in replacing the hydrogen bonded to the carbonyl carbon with a –OH group. 2. Ketones, do not have this hydrogen and do not react with mild oxidizing agents. ...
... Oxidation of Aldehydes Produces a carboxylic acid 1. Aldehyde oxidation results in replacing the hydrogen bonded to the carbonyl carbon with a –OH group. 2. Ketones, do not have this hydrogen and do not react with mild oxidizing agents. ...
Substitution Reactions of Alcohols
... We have looked at substitution reactions that take place via two mechanisms: SN1 - works for substrates that can form relatively stable carbocations... SN2 - works best for substrates where the carbon that bears the leaving group is sterically uncluttered. ...
... We have looked at substitution reactions that take place via two mechanisms: SN1 - works for substrates that can form relatively stable carbocations... SN2 - works best for substrates where the carbon that bears the leaving group is sterically uncluttered. ...
Converting Alcohols to Alkyl Halides – The Mitsunobu Reaction
... We have looked at substitution reactions that take place via two mechanisms: SN1 - works for substrates that can form relatively stable carbocations... ...
... We have looked at substitution reactions that take place via two mechanisms: SN1 - works for substrates that can form relatively stable carbocations... ...
Ch 23 Carbonyl Condensations
... - The first part is an alpha substitution, where the deprotonated C is the Nu and a + carbon (generally a carbonyl) on another molecule is the E+. - If the other molecule’s carbonyl has no LG, the reaction proceeds as Nu addition. - If the carbonyl does have an LG, the reaction proceeds as Nu sub ...
... - The first part is an alpha substitution, where the deprotonated C is the Nu and a + carbon (generally a carbonyl) on another molecule is the E+. - If the other molecule’s carbonyl has no LG, the reaction proceeds as Nu addition. - If the carbonyl does have an LG, the reaction proceeds as Nu sub ...
Organic Chemistry II / CHEM 252 Chapter 16
... • Dissolving aldehydes (or ketones) in water causes formation of an equilibrium between the carbonyl compound and its hydrate – The hydrate is also called a gem-diol (gem i.e. geminal, indicates the presence of two identical substituents on the same carbon) – The equilibrum favors a ketone over its ...
... • Dissolving aldehydes (or ketones) in water causes formation of an equilibrium between the carbonyl compound and its hydrate – The hydrate is also called a gem-diol (gem i.e. geminal, indicates the presence of two identical substituents on the same carbon) – The equilibrum favors a ketone over its ...
2.10 Reactions of alcohols
... 2.10 Reactions of alcohols c. describe the following chemistry of alcohols: i. combustion ii. reaction with sodium iii. substitution reactions to form halogenoalkanes, including reaction with PCl5 and its use as a qualitative test for the presence of the –OH group iv. oxidation using potassium dichr ...
... 2.10 Reactions of alcohols c. describe the following chemistry of alcohols: i. combustion ii. reaction with sodium iii. substitution reactions to form halogenoalkanes, including reaction with PCl5 and its use as a qualitative test for the presence of the –OH group iv. oxidation using potassium dichr ...
Wolff rearrangement
The Wolff rearrangement is a reaction in organic chemistry in which an α-diazocarbonyl compound is converted into a ketene by loss of dinitrogen with accompanying 1,2-rearrangement. The Wolff rearrangement yields a ketene as an intermediate product, which can undergo nucleophilic attack with weakly acidic nucleophiles such as water, alcohols, and amines, to generate carboxylic acid derivatives or undergo [2+2] cycloaddition reactions to form four-membered rings. The mechanism of the Wolff rearrangement has been the subject of debate since its first use. No single mechanism sufficiently describes the reaction, and there are often competing concerted and carbene-mediated pathways; for simplicity, only the textbook, concerted mechanism is shown below. The reaction was discovered by Ludwig Wolff in 1902. The Wolff rearrangement has great synthetic utility due to the accessibility of α-diazocarbonyl compounds, variety of reactions from the ketene intermediate, and stereochemical retention of the migrating group. However, the Wolff rearrangement has limitations due to the highly reactive nature of α-diazocarbonyl compounds, which can undergo a variety of competing reactions.The Wolff rearrangement can be induced via thermolysis, photolysis, or transition metal catalysis. In this last case, the reaction is sensitive to the transition metal; silver (I) oxide or other Ag(I) catalysts work well and are generally used. The Wolff rearrangement has been used in many total syntheses; the most common use is trapping the ketene intermediate with nucleophiles to form carboxylic acid derivatives. The Arndt-Eistert homologation is a specific example of this use, wherein a carboxylic acid may be elongated by a methylene unit. Another common use is in ring-contraction methods; if the α-diazo ketone is cyclic, the Wolff rearrangement results in a ring-contracted product. The Wolff rearrangement works well in generating ring-strained systems, where other reactions may fail.