Diels-Alder reaction between butadiene and maleic anhydride

Objective The objective of this practice is the realization of a Diels-Alder cycloaddition between a diene and an alkene to obtain a highly functionalized cyclohexene derivative. Background Diels-Alder reaction is one of the most remarkable chemical reactions discovered in the 20th century. The authors of this reaction won the Nobel Prize in 1950. It is … Read more

Stereospecific synthesis of trans-1,2-cyclohexanediol

Objetives To perform a stereospecific synthesis, as well as to show the relevance of epoxides (oxacyclopropanes) as versatile intermediates in Organic Synthesis. Background In this experiment, trans-cyclohexane-1,2-diol is obtained from cyclohexene, prior to the transformation of the latter into trans-2-bromocyclohexanol by a stereoselective process (anti addition to a double bond), followed by the formation of … Read more

Advanced Organic Synthesis Experiments

Organic synthesis is a branch of chemistry that focuses on the construction of complex organic molecules from simpler starting materials. In an advanced organic synthesis experimental course, students learn how to design and carry out experiments to synthesize a wide range of organic compounds. One of the key skills that students develop in an advanced … Read more

Synthesis of aspirin

Objective of Aspirin Synthesis: Purpose and Application The purpose of this experiment is to familiarize the students with the reaction of esterification getting aspirin (acetyl salicylic acid) from the salicylic acid and acetic anhydride.   3D structure Historical and Scientific Background of Aspirin Synthesis Acetylsalicylic acid is marketed under the name of aspirin for the … Read more

Lassaigne’s test

What is Lassaigne’s test? Lassaigne’s test (sodium fusion test) is one of the most widely used methods (in qualitative organic qualitative analysis) for the determination of nitrogen in organic compounds. In addition, it can be used for the determination of sulfur, halogens and phosphorus. Briefly, in the Lassaigne’s, the substance to be examined is melted … Read more

Obtaining t-butyl chloride for the synthesis of 1,4-di-t-butylbenzene

Objetives Perform an electrophilic aromatic SEAr substitution reaction, particularly a Friedel-Craft alkylation in tert-butylbenzene. Background The Friedel-Crafts alkylation reaction of aromatic rings is a C-C bond forming reaction, which often uses alkyl halides (R-X) as alkylating agents and a Lewis acid (AlCl3) as catalyst. However, this reaction has some limitations since, firstly, the primary alkyl … Read more

Claisen-Schmidt condensation: α,β-unsaturated ketones

Objective The purpose of this experiment is to perform a Claisen-Schmidt condensation. That is, a cross aldol condensation between a non-enolizable aldehyde and an enolizable ketone. Background Claisen-Schmidt condensation is a type of aldol condensation, which consists of the synthesis of α,β-unsaturated ketones by condensation of an aromatic aldehyde with a ketone. As the aromatic … Read more

Synthesis of benzoic acid from Grignard reagent

Objective Students will familiarized with the strict anhydrous conditions involved in the use of Grignard reagents, and in this case for obtaining benzoic acid by the carbonation reaction of a Grignard reagents. Background One of the most popular methods of forming C-C bonds in organic synthesis is through the use of Grignard reagents (Nobel Prize in … Read more

Synthesis of 2-aminobenzoic acid (anthranilic acid)

Objetives Synthesis of 2-aminobenzoic acid (anthranilic acid) from phthalimide by a bromine-promoted Hofmann transposition reaction in basic medium. Background The Hofmann transposition of an amide to form an amine with loss of carbon dioxide (CO2) is an example of a reaction in which alkyl or aryl groups migrate to electron-deficient nitrogen atoms. Other examples of … Read more

Obtaining β-naphthyl methyl ether

Objective The purpose of this experiment is to obtain an asymmetric ether of industrial interest from naphthalen-2-ol (β-naphthol) using two synthetic methods. Background Ethers can be obtained from alcohols by nucleophilic substitution reactions (SN2). 2-methoxynaphthalene (β-naphthyl methyl ether) is a white solid with a melting point of 73 °C and is known commercially as neroline. … Read more