Ethanoic acid esterification

An example of a reversible reaction in the liquid phase is afforded by the esterification reaction between ethanol and acetic (ethanoic) acid forming ethyl acetate and water. Since, however, ethyl acetate undergoes conversion to acetic acid and ethanol when heated with water, the esterification reaction never proceeds to completion. 

This is essentially true, as is evidenced by the rates of esterification in alcoholic media of propan-l-ol with ethanoic acid [27] or of propan-2-ol with mesitoic acid [28], The absence of a specific microwave effect became apparent from several experiments carefully conducted in alcohols or in DMF under similar conditions but with microwave or classical heating [7]. 

Worked Example 3.12 What fragments do we need to consider during the esterification of 1-butanol with ethanoic acid ... 

As mentioned, esterification is reversible, and with ethanol and ethanoic acid the equilibrium constant for the liquid phase is about 4 (AG° = —0.8 kcal) at room temperature, which corresponds to 66% conversion to ester ... 

Exercise 18-10 Predict the outcome of an attempted esterification of ethanoic acid with fert-butyl aicoho in the presence of dry HCI. 

It is convenient to consider the synthesis of vinyl acetate at this point, because it involves the aerobic oxidation of ethene to the unstable intermediate ethenol (H2C=CH(OH)), followed by its immediate esterification with acetic (ethanoic) acid,... 

Since salicylic acid has both an alcohol functional group and a carboxylic acid functional group, it can undergo two different esterification reactions depending on which functional group reacts. For example, when treated with ethanoic acid (acetic acid), salicylic acid behaves as an alcohol and the ester produced is acetylsalicylic acid (aspirin). On the other hand, when reacted with methanol, salicylic acid behaves as an acid and the ester methyl salicylate (oil of wintergreen) is produced. Methyl salicylate is also an analgesic and part of the formulation of many liniments for sore muscles. What are the structures of acetylsalicylic acid and methyl salicylate ... 

Most people are familiar with ethanol as being the active constituent of beers, wines and spirits, whereas ethanoic acid is usually associated with chips - it is in vinegar. When the two substances are mixed, they react slowly to form a compound, an ester called ethyl ethanoate it has a distinctive sweet and fruity smell, and is used to make varnishes and glues. This esterification reaction, which is typical of alchohols and organic acids (see Module 7), is relatively easy to monitor and so... 

Fig. 4.5. Comparative conversions under the action of MW and A during esterification of propanol with ethanoic acid, (a) H2SO4 catalyst, A (b) H2SO4 catalyst, MW (c) silica catalyst. A (d) silica catalyst, MW.

Fmn 23g of ethanol are obtained 36g of ethyl ethanoate by esterification widi edianoic acid in the presence of coiicenoaied sulphuric add. What is the pcicent e yield of the teacdon ... 

The reaction of ethanol with ethanoic acid (in the presence of sulfuric acid catalyst) produces a sweet-smelling compound known as an ester. The production of an ester is called esterification. The name of the particular ester produced in this reaction is ethyl ethanoate ... 

In a typical example of an esterification reaction, glacial ethanoic acid is heated with ethanol in the presence of concentrated sulfuric acid, which acts as the catalyst. The sweet-smelling ester ethyl ethanoate is formed ... 

The functional gronp in esters is the —COOR group. In the presence of an acid catalyst, such as HCl, esters hydrolyze to yield a carboxylic acid and an alcohol (the opposite of esterification). For example, in an add solution, ethyl acetate hydrolyzes to ethanoic acid (acetic acid) and ethanol ... 

The esterification reaction between ethanoi and ethanoic acid has a free energy change (AG ) of -4.38kJ moi", Caicuiate the vaiue of K for this reaction at 25°C (298K). (/ = 8.31 moH)... 

Some organic reactions have very large equilibrium constants, large negative values of and are quantitative. However, many reactions have much smaller equilibrium constants and correspondingly smaller AG° values. For example, the esterification reaction of ethanoic acid and ethanol has an equilibrium constant of 4 and = —1.7 kj mole" at 298 K. 

How do the equilibrium constant expressions differ for the hydrolysis reaction of ethyl ethanoate (written right to left) and the esterification reaction of ethanol and ethanoic acid (written left to right) What is the equilibrium constant for the hydrolysis reaction ... 

For example, propyl ethanoate, which is the ester responsible for the flavor and odor of pears can be prepared using ethanoic acid and 1-propanol. The equation for this esterification is written as... 

Figure 7 presents polycondensation using the example of polyesterification. As in the reaction illustrated above of ethanol and ethanoic (acetic) acid, producing acetic acid ethylester (ethyl acetate), only the functional groups are essentially important in describing esterification. Bifunctional monomers are required for polycondensation. In the example of polyesterification, diols such as ethandiol (glycol) and dicarboxylic acids such as terephthalic acid are used. 

---