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- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/22%3A_Carbonyl_Alpha-Substitution_Reactions/22.07%3A_Reactivity_of_Enolate_IonsAlthough reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are more common, partially due to the thermodynamic stability of the C=O bonds in the final ...Although reactions with the nucleophilic oxygen are possible, reactions involving the nucleophilic α-carbon are more common, partially due to the thermodynamic stability of the C=O bonds in the final products. If the alpha carbon of the starting material has a defined stereochemistry or if a new stereocenter is formed during the reaction, the product will a racemic mixture of enantiomers.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/27%3A_Biomolecules_-_Lipids/27.08%3A_Biosynthesis_of_SteroidsThe mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydrope...The mechanism for the flavin-hydroperoxide-dependent epoxidation of squalene is initiated by the nucleophilic attack of the pi electrons of a squalene double bond on the electrophilic terminal hydroperoxide oxygen. Thus, each 1,2-hydride or 1,2-methyl shift occurs to the backside of the orbital connected to the leaving group in what can be viewed as a series of nucleophilic substitution reactions – where σ-bonding electron pairs serve as the nucleophiles.
- https://chem.libretexts.org/Courses/Martin_Luther_College/Organic_Chemistry_-_MLC/04%3A_Carbonyls/4.02%3A_Carboxylic_Acids/4.2.05%3A_Chemistry_of_EstersIn the first two steps of the mechanism, the OR leaving group from the ester is replaced by the R group from the Grignard reagent through a nucleophilic acyl substitution. 2) Draw the product of the r...In the first two steps of the mechanism, the OR leaving group from the ester is replaced by the R group from the Grignard reagent through a nucleophilic acyl substitution. 2) Draw the product of the reaction between the following molecule and LiAlH 4 , and the product of the reaction between the following molecule and DIBAL.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/24%3A_Amines_and_Heterocycles/24.S%3A_Amines_and_Heterocycles_(Summary)The Curtius rearrangement converts an acid chloride to an amine by the migration of an -R group form the carbonyl carbon to the the neighboring nitrogen in the acyl azide intermediate. Skill 24.13 Use...The Curtius rearrangement converts an acid chloride to an amine by the migration of an -R group form the carbonyl carbon to the the neighboring nitrogen in the acyl azide intermediate. Skill 24.13 Use the Henderson‑Hasselbalch equation to calculate the percentage of a base that is protonated in a solution, given the pK a value of the associated ion and the pH of the solution.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/21%3A_Carboxylic_Acid_Derivatives-_Nucleophilic_Acyl_Substitution_Reactions/21.02%3A_Naming_Carboxylic_Acid_DerivativesIf the corresponding carboxylic acid has an –oic acid or –ic acid ending it is removed and replaced with the ending -oyl followed by the first syllable of the name of the halogen along with an –ide en...If the corresponding carboxylic acid has an –oic acid or –ic acid ending it is removed and replaced with the ending -oyl followed by the first syllable of the name of the halogen along with an –ide ending. The acid halide functional group is assumed to be on the end of the parent chain, so it is not necessary to include the functional group location number in the name.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/16%3A_Chemistry_of_Benzene_-_Electrophilic_Aromatic_Substitution/16.S%3A_Chemistry_of_Benzene_-_Electrophilic_Aromatic_Substitution_(Summary)The first is addition of the electrophile to the ring and the second is elimination of a hydrogen from the ring to re-form the pi bond and restore aromaticity. In bromination of an aromatic ring, mole...The first is addition of the electrophile to the ring and the second is elimination of a hydrogen from the ring to re-form the pi bond and restore aromaticity. In bromination of an aromatic ring, molecular bromine (Br 2 ) is reacted with iron tribromide (FeBr 3 ) to form the strongly electrophilic bromine cation and FeBr 4 . Following this, the aromatic ring is reacted with the bromine cation and adds to the ring to form a benzenonium cation.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/04%3A_Organic_Compounds_-_Cycloalkanes_and_their_Stereochemistry/4.07%3A_Axial_and_Equatorial_Bonds_in_CyclohexaneThe hydrogens of cyclohexane exist in two distinct locations - axial and equatorial. The two chair conformations of cyclohexane rapidly interconverts through a process called ring flip.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/20%3A_Carboxylic_Acids_and_Nitriles/20.01%3A_Chapter_Objectives_and_Introduction_to_Carboxylic_AcidsNaturalists of the 17th century knew that the sting of a red ant’s bite was due to an organic acid that the ant injected into the wound. A mnemonic phrase for the C 10 to C 20 natural fatty acids capr...Naturalists of the 17th century knew that the sting of a red ant’s bite was due to an organic acid that the ant injected into the wound. A mnemonic phrase for the C 10 to C 20 natural fatty acids capric, lauric, myristic, palmitic, stearic and arachidic is: "Curly, Larry & Moe Perform Silly Antics" (note that the names of the three stooges are in alphabetical order).
- https://chem.libretexts.org/Courses/University_of_Alberta_Augustana_Campus/AUCHE_250%3A_Organic_Chemistry_I/06%3A_Substitutions/6.02%3A_Characteristics_of_the_SN2_ReactionIf each of the three substituents were hydrogen atoms, as illustrated in the first example below, there would be little steric repulsion created in the planar portion of the transition state thereby i...If each of the three substituents were hydrogen atoms, as illustrated in the first example below, there would be little steric repulsion created in the planar portion of the transition state thereby increasing the ease at which the nucleophilic substitution reaction occurs. As Size Increases, Basicity Decreases: In general, if we move from the top of the periodic table to the bottom of the periodic table as shown in the diagram below, the size of an atom will increase.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/23%3A_Carbonyl_Condensation_Reactions/23.07%3A_Intramolecular_Aldol_ReactionsMolecules which contain two carbonyl functionalities have the possibility of forming a ring through an intramolecular aldol reaction. The term “Intramolecular” means “within the same molecule.” In thi...Molecules which contain two carbonyl functionalities have the possibility of forming a ring through an intramolecular aldol reaction. The term “Intramolecular” means “within the same molecule.” In this case, it means that the enolate donor and the electrophilic acceptor of an aldol reaction are contained in the same molecule such as dialdehydes, keto aldehydes, or diketones. In these cases, the small distance between the donor and acceptor leads to faster reaction rates.
- https://chem.libretexts.org/Courses/Smith_College/Organic_Chemistry_(LibreTexts)/20%3A_Carboxylic_Acids_and_Nitriles/20.05%3A_Substituent_Effects_on_AcidityYou have already seen how the presence of an electron‑withdrawing or electron‑releasing group affects the stability of a positively charged carbocation. Now you see how these groups affect the stabili...You have already seen how the presence of an electron‑withdrawing or electron‑releasing group affects the stability of a positively charged carbocation. Now you see how these groups affect the stability of carboxylate anions, and in turn, determine the dissociation constant of a carboxylic acid.
