Synthesis of acetylferrocene

Objective To prepare acetylferrocene by electrophilic substitution on one of the cyclopentadiene rings of ferrocene (bis(η5-cyclopentadienyl) iron(II)). Background The serendipitous discovery, in 1951, of ferrocene opened an entire, new area of research and contributed greatly to the technological advance of Chemistry. Among the uses and applications of ferrocene, the following bear noting: Aviation fuel catalyst, … Read more

Oxidative coupling of alkynes (Glaser-Eglinton-Hay)

Objective To study the oxidative coupling of alkynes with the Glaser-Eglinton-Hay coupling; with is the oldest of the acetylenic couplings. Background Glaser-Eglinton-Hay coupling involves the reaction of the ethylenic compound with cuprous salts in the pres- ence of oxygen and a base (ammonia initially). Subsequent modifications to this reaction changed the reaction conditions (reagents and … Read more

Chiral resolution of (±)-α-methylbenzylamine

Objetive To acquaint students with the concept of chiral resolution: separation of the two enantiomers of a chiral compound. In this case, the different solubility of two diastereomeric salts in water will be used. Background When products, reagents, or non-chiral catalysts are used in a chemical reaction in which there are chiral centers, the overall … Read more

Preparation of N-(p-chlorophenyl)-maleimide

Objetive To prepare a cyclic amide from p-chloroaniline and maleic anhydride. Background Obtaining N-(p-chlorophenyl)-maleimide from the p-chloroaniline and maleic anhydride is a two-step process. First, a nucleophilic attack of the nitrogen (aromatic amine), catalyzed by the acid medium on the carboxylic carbon of the cyclic anhydride, occurs. In the second step, the N-(p-chlorophenyl)-maleamic acid is … Read more

Obtaining sunflower oil from seeds (Soxhlet)

Objective To learn how to set up Soxhlet extraction to obtain oil from sunflower seeds. Background Vegetable oils are mainly triglycerides from seeds or fruits. They are a key component of the human diet and are also used for other purposes, including the production of biofuels (biodiesel), lubricants, and cosmetics such as soaps and creams. … Read more

Benzoin synthesis and reactions

Objective To form the C−C bond via condensation reaction of benzaldehyde catalyzed by cyanide ion or thiamine, and to perform the stereoselective reduction of benzoin. Background One of the most important processes in Organic Synthesis is the formation of carbon-carbon bonds. Usually, this reaction requires the formation of a carbanion (carbon nucleophile) and its reaction … Read more

Synthesis of n-butylbarbituric acid

Objective To perform a two-step synthesis for the preparation of a derivative of barbituric acid. In the first step, the diethyl n-butylmalonate is prepared, which is subsequently reacted with urea in the presence of a strong base, such as NaOEt, to yield the desired compound. Background Barbiturates are drugs that are prescribed to treat severe … Read more

Synthesis of (±)-α-methylbenzylamine

Objective To perform a reductive amination of a carbonyl compound, emulating the biosynthesis of an amino acid but without using enzyme catalysis. Background When reagents, products, and non-chiral catalysts are used in a chemical reaction, the overall result is an optically inactive mixture. However, if a center or chiral carbon has been generated, the product … Read more

Benzocaine synthesis

Objective To provide an example of multi-step synthesis (using protecting groups) by preparing an organic compound, benzocaine, that is present in many consumer products. Background Benzocaine (ethyl 4-aminobenzoate) is an anesthetic that is also used to relieve the pain of injuries and burns. Benzocaine is the derivative of p-aminobenzoic acid and can be synthesized via … Read more

Preparation of 1-bromobutane

Objective To produce n-butyl bromide from n-butyl alcohol, and to demonstrate the ability to carry out a substitution reaction in organic chemistry, specifically the conversion of an alcohol to an alkyl halide. Background Reacting a primary alcohol with a hydrogen halide produces a primary alkyl halide. The reaction follows an SN2 mechanism, as the dehydration step … Read more