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Esters are an important class of organic compounds commonly prepared from the esterification reaction of an organic acid with an alcohol in the presence of a strong mineral acid (usually H2SO4H2SO4 size 12{H rSub { size 8{2} } ital "SO" rSub { size 8{4} } } {}). They are chiefly responsible for the pleasant aromas associated with various fruits, and as such are used in perfumes and flavorings. Some esters also have useful physiological effects. The best known example is the analgesic ("pain killing") and anti-pyretic ("fever reducing") drug acetylsalicylic acid, otherwise known by its trade name aspirin.

Liniments used for topical relief of sore muscles contain the ester methyl salicylate ("oil of wintergreen"), which is prepared from the reaction of methyl alcohol with the acid group of salicylic acid. Methyl salicylate acts as an analgesic and is absorbed through the skin; however, methyl salicylate is also a skin irritant (like many organic substances), which in this instance provides the beneficial side effect of the sensation of warming in the area of the skin where the liniment is applied.

Oxidation of a primary alcohol may yield either an aldehyde or a carboxylic acid, depending on the reaction conditions. For example, mild oxidation of ethanol produces acetaldehyde, which under more vigorous conditions may be further oxidised to acetic acid. The oxidation of ethanol to acetic acid is responsible for causing wine to turn sour, producing vinegar.

A number of oxidising agents may be used. Acidified sodium dichromate (VI) solution at room temperature will oxidise primary alcohols to aldehydes and secondary alcohols to ketones. At higher temperatures primary alcohols are oxides further to acids.

Figure 1

The dichromate solution turns from the orange color of the Cr2O72−Cr2O72− size 12{ ital "Cr" rSub { size 8{2} } O rSub { size 8{7} } rSup { size 8{2 - {}} } } {} (aq) to the blue color of the Cr3+Cr3+ size 12{ ital "Cr" rSup { size 8{3+{}} } } {} (aq). This color change is the basis for the "breathalyser test". The police can ask a motorist to exhale through a tube containing some orange crystals. If the crystals turn blue, it shows that the breath contains a considerable amount of ethanol vapor.

Soaps are produced by the reaction of metallic hydroxides with animal fats and vegetable oils. The major components of these fats and oils are triglycerides. Triglycerides are esters of the trihydroxy alcohol called glycerol and various long-chain fatty acids. Tristearin is a typical triglyceride. Upon reaction with sodium hydroxide, the ester bonds of tristearin are broken. The products of the reaction are the soap, sodium stearate, and glycerol. This type of reaction is called saponification (Greek: sapon, soap) and it is depicted below.

Figure 2

Soap is made commercially by heating beef tallow in large kettles with an excess of sodium hydroxide. When sodium chloride is added to this mixture (called the "saponified" mixture), the sodium salts of the fatty acids separate as a thick curd of crude soap. Glycerol is an important by-product of the reaction. It is recovered by evaporating the water layer. The crude soap is purified, and coloring agents and perfumes are added to meet market demands.

Saponification of a vegetable oil

CAUTION - Sodium hydroxide is a very caustic material that can cause severe skin burns. Eye burns caused by sodium hydroxide are progressive: what at first appears to be a minor irritation can develop into a severe injury unless the chemical is completely flushed from the eye. If sodium hydroxide comes in contact with the eye, flush the eye with running water continuously for at least 20 minutes. Notify your TA immediately. If sodium hydroxide is spilled on some other parts of the body, flush the affected area with running water continuously for at least 2-3 minutes. Notify your TA immediately.

Never handle sodium hydroxide pellets with your fingers. Use weighing paper and a scoopula. Solid sodium hydroxide will absorb water from the atmosphere. It is hygroscopic. Do not leave the container of sodium hydroxide open.

Keep ethanol and ethanol-water mixtures away from open flames.

Aqueous iron chloride will stain clothes permanently and is irritating to the skin. Avoid contact with this material.

 

In this experiment, you will saponify a vegetable oil

1. Pour 5 mL (5.0 g) of vegetable oil into a 250-mL beaker.
2. Slowly dissolve 2.5 g of NaOH pellets in 15 mL of the 50% ethanol/water mixture in a 50-mL beaker.
3. Add 2-3 mL of the NaOH solution to the beaker containing the oil. Heat the mixture over a hot plate with stirring. CAUTION: Keep your face away from the beaker and work at arm's length. Stirring is required to prevent spattering. Every few minutes, for the next 20 minutes, add portions of the ethanol/water mixture while continuing to stir to prevent spattering. After about 10 more minutes of heating and stirring, the oil should be dissolved and a homogenous solution should be obtained.
4. Add 25 mL of water to the hot solution. Using the hot grips, pour this solution into a 250 mL beaker containing 150 mL of saturated NaCl solution. Stir this mixture gently and permit it to cool for a few minutes.
5. Skim the soap layer off the top of the solution and place it in a 50-mL beaker.
6. Into a test tube, place a pea-sized lump of your soap. Place a similar amount of laundry detergent in a second tube and a similar amount of laundry detergent in a second tube and a similar amount of hand soap in a third tube. Add 10 mL of water to each tube. Stopper each tube and shake thoroughly.
7. Estimate the pH of the solution using wide-range indicator solution or wide-range test paper. Record the results. Pour the contents of the test tubes into the sink and rinse the tubes with water.

Figure 3

 

Remember to describe what happens and explain the color changes.

What conditions and techniques would favour the oxidation of ethanol to

a. ethanal rather than ethanoic acid.

b. ethanoic acid rather than ethanal?

Remember to describe what happens and explain the color changes.

What is your final product?

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