Carboxylic acid derivatives include the carboxylates, amides, and esters. Also anhydrides, acyl halides, thioesters and acyl phosphates. Of the latter group, anhydrides and acyl halides don't appear in biochemistry, so while they are important for general organic chemistry, the new MCAT in not be so interested in them. However, thioesters and acyl phosphates do figure prominently in biochemistry. In fact, having a high free energy, the status of thioesters and acyl phosphates as the prototypical activated acyl compounds in biochemistry makes them among the most important types of organic molecules to understand.
Acyl Compounds Mechanisms
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Conceptual Vocabulary for Carboxylic Acids and Derivatives
Carboxylic Acids and Derivatives
Carboxylic acids are organic acids characterized by the presence of a carboxyl group.
Esters are a class of chemical compounds and functional groups which consist of an inorganic or organic acid in which at least one hydroxyl group has been replaced by an alkoxy group.
Nucleophilic acyl substitution describes the substitution reaction involving nucleophiles and carboxylic acid derivatives including esters, amides and acid halides.
Amides are a class of chemical compounds and functional groups in which a carbonyl group carbon is linked to a nitrogen atom.
An acyl or acid halide is a chemical compound derived from an acid by replacing a hydroxyl group with a halide group.
Hydrolysis is a chemical reaction or process in which a chemical compound is broken down by reaction with water.
A condensation reaction is a chemical reaction in which two molecules or moieties combine to form one single molecule, together with the loss of a small molecule.
An acyl group is a functional group derived by the removal of one or more hydroxyl group from an oxoacid.
Esterification is the general name for a chemical reaction in which two chemicals, such as an alcohol and an acid, form an ester as the reaction product.
An acid anhydride is an organic compound which has two acyl groups bound to the same oxygen atom.
Fischer esterification is the process of forming an ester by refluxing a carboxylic acid and an alcohol in the presence of an acid catalyst.
Saponification is the hydrolysis of an ester under basic conditions to form an alcohol and the salt of a carboxylic acid.
Acetylation or ethanoylation describes a reaction that introduces an acetyl functional group into an organic compound.
Aminolysis is any chemical reaction in which a molecule is split into two parts by reacting with a molecule of ammonia or an amine.
The Hell-Volhard-Zelinsky halogenation reaction halogenates carboxylic acids at the alpha carbon.
The Hofmann rearrangement is the organic reaction of a primary amide to form a primary amine with one fewer carbon atom.
In the malonic ester synthesis, diethyl malonate or a similar ester is alkylated at the carbon alpha to both carbonyl groups, and then converted to a substituted acetic acid.
The Knoevenagel condensation reaction is a modification of the Aldol condensation in which nucleophilic addition occurs of an active hydrogen compound, which is a substance capable of adding hydrogens to an enolate anion, followed by an dehydration reaction.
The Arndt-Eistert synthesis is a series of chemical reactions designed to convert a carboxylic acid to a carboxylic acid homologue with one additional carbon atom.
The Curtius rearrangement is a chemical reaction that involves the rearrangement of an acyl azide to an isocyanate.
The Schmidt reaction involves alkyl migration over the carbon to nitrogen chemical bond in an azide with expulsion of nitrogen.
The Dakin-West reaction is a chemical reaction that transforms an amino-acid into an amino-ketone using a acid anhydride and a base, typically pyridine.
The Fries rearrangement is a rearrangement reaction of a phenyl ester to a hydroxy aryl ketone by catalysis of lewis acids.
The Reformatskii reaction is an organic reaction which condenses aldehydes or ketones with alpha-halo esters in the presence of metallic zinc to form beta-hydroxy-esters.