Amide Formation from Acid Halides
Addition of primary and secondary amines (or ammonia) to acid chloride results in amides.
Carboxylic Acid Derivatives
25 reactions in this topic, each with the reagents, the mechanism and the structure of the product.
Amide Formation Using DCC
Treatment of carboxylic acids with amines in the presence of the dehydrating agent N,N’-dicyclohexylcarbodiimide (DCC) leads to th
Beckmann Rearrangement
The Beckmann rearrangement is a reaction of oximes that can result in either amides or nitriles, depending on the starting materia
Claisen condensation
When esters are treated with strong base, an enolate can be formed. By the attack of an ester enolate on a carbonyl group generate
Conversion to aldehydes [LiAlH(OtBu)3]
Addition of the bulky reducing reagent lithium tri-t-butoxy aluminum hydride [LiAlH(OtBu)3] to acid chlorides results in the forma
Conversion to amides [RNH2]
Addition of primary and secondary amines (or ammonia) to acid chloride results in amides.
Conversion to anhydrides [RCO2(–)]
Addition of a carboxylic acid to an acid chloride results in the anhydride.
Conversion to esters [ROH]
Acid chlorides are converted to esters when treated with alcohols. This reaction called alcoholysis.
Curtius Rearrangement
The Curtius rearrangement is a rearrangement of acyl azides to give isocyanates, expelling the nitrogen gas. The isocyanates can t
Dehydration of amides to nitriles [P2O5]
Primary amides can be converted to nitriles with a dehydrating reagent such as P2O5.
Ester formation [RCO2(–)]
Alkyl halides (or tosylates) will react with carboxylate ion to form esters in SN2 reaction.
Esterification
Esterification is a chemical reaction that occurs between the acid (usually carboxylic acid) and the alcohol (or compounds contain
Formation of Diazonium Salts
Treatment of aromatic amines with sodium nitrite and HCl leads to the formation of diazonium salts.
Gabriel Synthesis of amines
The Gabriel synthesis is a method for making primary amines through an SN2 reaction of a phthalimide with an alkyl halide followed
Grignard addition to aldehydes
Treatment of an aldehyde with Grignard reagent followed by water (acid) forms usually a secondary alcohol with a new carbon-carbon
Hofmann rearrangement
When amides are treated with halide and base, a rearrangement occurs, resulting in the loss of carbon dioxide and the formation of
Hydrolysis to carboxylic acid [acidic]
When an ester is treated with aqueous acid (and heat) it is converted into a carboxylic acid.
Hydrolysis to carboxylic acid [basic]
Esters can be converted to carboxylic acids through treatment with strong base.
Hydrolysis to carboxylic acids
Addition of water and acid to a nitrile leads to the formation of a carboxylic acid.
Reactions of Diazonium Salts
Treatment of diazonium salts with various reagents leads to the formation of a new bond to the aromatic ring and loss of nitrogen
Reduction to alcohols [LiAlH4]
Addition of lithium aluminum hydride to esters leads to the formation of primary alcohols (after addition of acid).
Reduction to aldehydes [DIBAL-H]
Esters can be reduced to aldehydes with diisobutylaluminum hydride (DIBAL) a bulky source of hydride ion.
Reduction to amines [LiAlH4]
Lithium aluminum hydride, LiAlH4 [but NOT sodium borohydride, NaBH4] can reduce nitriles to primary amines.
Reductive Amination
Aldehydes and ketones can be converted into amines, through the formation of an imine and treatment with a reducing agent.
Transesterification [basic conditions]
Esters react with alcohols in a transformation called transesterification. This allows for the direct conversion of one ester into