Acetanilide synthesis

Objective Alternative acetanilide synthesis route to obtain aromatic amides without using acetic anhydride. Using instead acetic acid as acylating agent catalyzed by zinc. Background The acetanilide synthesis, or acetamides in general, are usually carried out from an amine (aromatic or aliphatic) with acetic anhydride. Acetic anhydride, a reagent widely used in organic chemistry laboratories, irritates mucous … Read more

Simple distillation: obtaining ethanol from wine

Objective Determine the percentage of ethanol, EtOH, in wine “alcohol by volume” (ABV) using simple distillation and subsequent measurement of the density of the distillate with an alcoholmeter. Background One of the characteristics that must be specified in the documentation of alcoholic beverages, e.g. wines, is the percentage (%) of alcohol by volume of EtOH, … Read more

Cyclohexanol dehydration

Objective The production of an alkene (cyclohexene) by the acid-catalyzed dehydration reaction of an alcohol (cyclohexanol). Background A secondary alcohol, such as cyclohexanol, is dehydrated via an E1 mechanism, where the key intermediate is the cyclohexyl cation. This cation can react by either an elimination or a substitution reaction. To obtain the alkene in good … Read more

Oxidation of 4-chlorobenzyl alcohol to 4-chlorobenzoic acid

Objective The purpose of this experiment is to obtain a carboxylic acid by oxidation of a primary alcohol using hypochlorite as oxidant. Experimental procedure An alternative method to the use of carcinogenic chromium(VI) salts for the oxidation of alcohols is the use of a green oxidizing agent such as hypochlorite. One of the most common … Read more

Microscale/Miniscale – Isomerization of maleic acid (cis) to fumaric acid (trans)

Objetives Perform an isomerization reaction of C=C double bonds in acidic medium with both microscale an miniscale methodologies. Background Isomerization is a chemical reaction in which a molecule is converted into one of its structural isomers, a compound with the same molecular formula but a different arrangement of atoms. Double bonds are rigid structures where interconversion … Read more

Organic Synthesis Experiments

Image taken by Angel Sánchez In this section, we describe a series of practices related to the reactivity of functional groups that are usually studied in an experimental course of Organic Chemistry. Most of the experiments described correspond to one-step transformations. In addition, others deal with the multistep synthesis of a compound and the study … Read more

Fractional distillation of an acetone/water mixture

Objective Use of fractional distillation for the purification of mixtures of liquid substances with close boiling points. Background Water and acetone are miscible so that the only way to separate them once mixed is by distillation. Fractional distillation is indicated when the difference in the boiling point of the liquids to be separated is approximately … Read more

Basic Lab Operations Experiments

In these experiments of basic laboratory operations, a series of procedures and manipulations are described in order to familiarize the student with the routine work of an organic chemistry laboratory. Image taken by Angel Sánchez Angel Sanchez Basic laboratory operations They can be defined as a series of basic procedures that are usually performed in … Read more

Synthesis of 2-acetylcyclohexanone

Objetives To produce a β-dicarbonyl compound, in this case 2-acetylcyclohexanone from cyclohexanone, using an enamine as a synthetic intermediate. Background Organometallic compounds and carbanions are not the only species used in organic synthesis with nucleophilic carbon atoms. The carbon in the β-position of an enamine has a nucleophilic character and can be alkylated or acylated … Read more

Wittig reaction for obtaining 4-vinylbenzoic acid

Objective The purpose of this experiment is to obtain alkenes from phosphonium salts and carbonyl compounds by means of the Wittig reaction. Background The Wittig reaction is named after its discoverer Georg Wittig (Nobel Prize winner in 1979) and consists of obtaining alkenes from phosphonium salts and carbonyl compounds. The carbon-carbon double bond C=C is … Read more