Experiments

Objective To perform the bromination of an alkene, avoiding using bromine Br2 reagent. Background The addition of halogens to alkenes is a process of great interest in Synthetic Organic Chemistry. The classical procedure is performed from the alkene and halogen. For bromination, the reagent used is bromine (Br2), which carries certain drawbacks and risks in … Read more

Objective To prepare adipic acid from cyclohexene by oxidation with H2O2 and sodium tungstate Na2WO4 using a sustainable alternative to the traditional method using potassium permanganate K2MnO4. Background Adipic acid is a substance used for the preparation of nylon, polyurethanes, and other products of commercial interest. The industrial synthesis of adipic acid uses nitric acid … Read more

Objective To synthesize α-glycol (pinacol) from ketone by radical condensation and to dehydrate α-glycol to form pinacolone. Background Glycols can be synthesized by numerous methods, and this product can be used as starting olefin or unsaturated carbonyl compounds. For example, from olefins the synthesis can be carried out by adding halogen, by adding hypohalogenous acid … Read more

Objective To demonstrate the regioselectivity of electrophilic addition to a double bond. This characteristic (regioselectivity) is not possible in the addition reaction to cyclohexene, because it is symmetrical. Background Electrophilic additions to double bonds are ones of the most common as well as the most powerful chemical transformations available. These reactions allow, starting from a … Read more

Objective To perform an electrophilic addition of a carbene to an alkene in order to allow the simultaneous formation of two C−C bonds, producing a cyclopropane derivative. Background Electrophilic additions to the double bonds are one of the most common transformations in an Organic Chemistry laboratory. They are also among the most powerful reactions in … Read more

Objective To familiarize the student with the reactions that produce organic polymers, a polyamide such as nylon. In this case a very simple technique called “interfacial polymerization” is used. Background Nylon is a synthetic polymer of the family of polyamides having great strength, providing the manufacture of fabrics for carpets, clothing, bands, ropes, hoses, conveyor … Read more

Objective To make soap by reacting a vegetable oil with sodium hydroxide NaOH (saponification reaction). Background Soap (metallic or carboxylate ester) forms as a product of a saponification reaction. It is called the reaction between a carboxylic acid and a strong base such as sodium hydroxide NaOH or potassium hydroxide KOH. The main feature is … Read more

Objective To produce a cyclic amide (lactam), key in nylon synthesis from a cyclic ketone, via a Beckmann rearrangement. Background Laurolactam (12-aminododecalactam) is used to synthesize polyamide-12, also known as Nylon-12, which is a semi-crystalline polyamide with very high tenacity and good chemical resistance. In this experiment, laurolactam is synthesized by a process of low … Read more

Objective To synthesis of 7-hydroxy-3-carboxycoumarin in water by a tandem reaction (Knoevenagel condensation  and Pinner reaction). Background Knoevenagel reaction is a condensation between an aldehyde or a ketone with an active hydrogen compound in the presence of a basic catalyst to yield α,β-unsaturated compounds. Usually the catalyst is a weakly basic amine, and the active hydrogen … Read more

Objective To perform a tandem aldol condensation / Michael addition reaction using an organocatalyst and to learn how to recover the organocatalyst. Background Organocatalysts are small organic molecules that can catalyze reactions in the absence of metals or metal ions. Proline is a chiral organic compound that can be used as a catalyst in many reactions … Read more