Experiments

Objective To produce ethyl iodide at microscale, from EtOH by a nucleophilic substitution reaction. Background Ethyl iodide is usually prepared in laboratories by the reaction of iodine, red phosphorus, and EtOH. The key step in this synthesis is the formation of the intermediate phosphorus triiodide, which reacts with EtOH to yield the desired product and … Read more

Objetives Epoxidation of an alkene, in this particular cyclohexene, using an easy-to-handle oxidant such as Oxone®. Background The typical procedure of alkene epoxidation calls for peracids in an organic solvent. One of the most common experimental methods consists of the reaction of peracetic acid in acetic acid. The peracid is generated in situ by the addition of … Read more

Objective To perform at microscale the addition of HBr to an alkene (hex-1-ene) to yield 2-bromohexane under phase-transfer catalyst conditions. Background Electrophilic addition ot HX to alkenes is a useful reaction for functional group interconversions. The reaction begins by a proton attack on the double bound and formation of a carbocation. These reactions are controlled … Read more

Objective To produce α- and β-ionone (violet perfume) from citral. These are cyclic terpenoid that occur in many essential oils. Background Citral (3,7-dimethyl-2,6-octadienal) is the main constituent of the essential oil of lemon grass (citronella). This natural product readily undergoes aldol condensation with acetone to give geranylacetone, which can be converted by cyclization under acidic … Read more

Objective To produce a macrocycle, in this case a derivative of calix[4]pyrrole as an example of a sequestering agent anion. Background Agents that selectively bind anions have attracted interest because of their role in biological and ecological processes. Two strategies have been designed to produce such compounds. The first involves the inclusion in the molecule … Read more

Objective To transform of cinnamaldehyde (2E)-3-phenylprop-2-enal) into 3-phenyl-2-propen-1-ol and 3-phenyl-propan-1-ol, using a single reagent, the LiAlH4, depending on the relative quantities and the addition order, in an inert atmosphere. Background The functional group interconversion (FGI) reactions are among the most common synthetic processes. In this experiment, the conversion of cinnamic aldehyde is performed by reduction … Read more

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

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

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

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