A typical procedure to synthesize esters is the Fischer esterification, wherein a carboxylic acid is treated with an alcohol in the presence of a mineral inorganic
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the reaction mixture to neutralize the resulting acid Acid anhydrides can also react with alcohols to produce esters Unlike the reactions between carboxylic
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A typical procedure to synthesize esters is the Fischer esterification, wherein a carboxylic acid is treated with an alcohol in the presence of a mineral inorganic
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Note that one product of the esterification reaction is water A simple experimental liquid and flow back down towards the reaction flask The side- arm between
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esters dans ce laboratoire est importante au point de vue de la synthèse car elle (En biologie, ce type de réaction porte le nom de synthèse par déshydratation
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catalytic flow Thus, the process should include low energy consumption, solvent- free system, minimum purification steps and should be environmentally friendly
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Organic acid, alcohol, ester, esterification BACKGROUND Did you methanol SAFETY • Concentrated sulfuric acid is used to catalyze the chemical reaction
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Fischer Esterification
Introduction:
Esters are one of the most common derivatives of carboxylic acids and are widely distributed in bothnature and industry. A typical procedure to synthesize esters is the Fischer esterification, wherein a
carboxylic acid is treated with an alcohol in the presence of a mineral inorganic acid catalyst. In this
experiment, lauric acid (dodecanoic acid) is converted to ethyl laureate. Lauric acid is representative
of a class of molecules called fatty acids. These are long, straight chain carboxylic acids (C12-C40)
found as ester derivatives in oils, fats, and waxes. For example, a component of carnuba wax is CH3(CH2)33CO2(CH2)26CH3. Carnuba wax is found in finer automobile waxes and is exuded by leaves of Brazilian wax palm tree. Animal fats are fatty acids of 1,2,3-propanetriol, also known as glycerol. Thus, these fats are often referred to as triglycerides. Objective: To synthesize ethyl laureate via Fischer esterification method. Experiment Overview: With 1º alcohols, neither side of the equilibrium depicted in equation 1 is strongly favored. To drive the equilibrium to make more ester, excess alcohol is added following Le Eq.1In addition, an acid catalyst is needed. Its role is to facilitate the nucleophilic attack of the alcohol at
the carbonyl carbon of the carboxylic acid. The tetrahedral intermediate formed by the attack of thealcohol can then isomerize by means of proton migration, to allow water to behave as a leaving group.
Loss of water yields a carbocation stabilized by resonance, which need only lose a proton to give the
desired ester, and regenerate the acid catalyst. In this experiment, the acid catalyst will be generated
in-situ (during the reaction) using acetyl chloride (CH3COCl) treated with a small amount of the ethanol used in the reaction mix, producing HCl, which then will initiate the reaction (shown in equation 2 below). Eq. 2