Organic Acids

Friday, September 23, 2022 7:13 PM

The homologous series of alkanoic acids has the general formula CnH2n+1COOH. Can be
represented as RCOOH as the COOH group is the active group and R is the rest of the molecule
which is generally unreactive.

Naturally found in:

• Vinegar - ethanoic acid
• Stinging needles and ant stings - methanoic acid
• Rancid butter - butanoic acid
• Citrus fruits - citric acid
• Milk - lactic acid

Preparation of Organic Acids

Oxidising alcohols will form the corresponding organic acid. E.g., ethanoic acid can be
prepared by boiling ethanol with potassium chromate(VI)

The product mixture is fractionally distilled to give pure organic acid

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Properties of Alkanoic Acids
Saturday, September 24, 2022 12:22 PM

Physical Properties
Organic acids are covalent compounds with a polar OH bond. The OH bond is even greater
than that of an alcohol because of the extra oxygen in the (O=C-O-H) bond. This oxygen is
highly electronegative and increases the pull of electrons away from the H in the OH group.

Organic acids only exist in liquid and solid forms and usually have higher boiling points than
their corresponding alcohols. E.g. the boiling point of ethanoic acid is 118° C compared to
ethanol's which is 87°C.
The increased polarity makes organic acids extremely soluble in water

Chemical Reactions
Organic acids are weak, and so only partially dissociate when dissolved in water to give free H+
ions.

This also makes them weak electrolytes.

They react like typical acids. They react with:

• Reactive Metals to give salt and H2 gas

• Carbonates and Hydrogen Carbonates to give salt, water and carbon dioxide

• Bases to produce salt and water

Anhydrous/dry organic acids give the following reactions

• Combustion in air or oxygen to give carbon dioxide and water

• Condensation or esterification
Organic acids combine with alcohols in the presence of concentrated sulphuric acid.
Water is removed (condensation) and compounds called esters are produced. The H2SO4
acts as a dehydrating agent and a catalyst.

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acts as a dehydrating agent and a catalyst.

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Esters
Saturday, September 24, 2022 3:20 PM

Esters are formed when alcohols and acids react

Naming Esters
When drawing esters, the acid part comes first, then the alcohol part.
When naming the compound, the alcohol part comes first, followed by the acid part. The
alcohol is named as a branch on the acid.

Larger samples of esters can be prepared by boiling a mixture of alcohol, anhydrous acid and
concentrated H2SO4 under reflux.
This allows continuous boiling without loss of volume to vapourisation.
The product is added to water. The ester floats on the surface and can be separated by
separating funnel.

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Properties of Esters
Saturday, September 24, 2022 3:41 PM

Physical Properties
-Esters are covalent, non-polar molecules held together by weak van-der-waals forces. The
strength of the force depends on the size of the molecule.
They are insoluble in water

Short chained organic acids (C1 - C6) produce esters which are oily, pleasant smelling liquids.
They are naturally found in fruits and flowers and are used in perfumes and flavourings.

Long chained organic acids produce esters commonly referred to as fats and oils. They are
greasy, scentless solids and liquids.

Fats and Oils

These are esters formed by the condensation of organic acids with a large hydrocarbon tail
and the tri-alcohol glycerol

Long chained organic acids:

C18H37COOH - stearic acid
C11H23COOH - lauric acid
C15H31COOH - palmitic acid

All of these organic acids can simply be represented as

Glycerol condenses with 3 fatty acid molecules to produce a fat molecule, a tri-ester

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Reactions of Esters

The functional group is the ester bond

Esters can undergo hydrolysis (the breakdown of the molecule by the addition of water).
There are 2 types of hydrolysis:

• Acid Hydrolysis - Boiling of the ester with dilute acid (HCl or H2SO4). This gives an organic
acid and alcohol

• Alkaline Hydrolysis - Boiling with aqueous alkali (NaOH or KOH). Yields the salt of the acid
and an alcohol.

As with inorganic salts, the salt formed has totally different properties from the acid. This
reaction is the basis of soap making or saponification.

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Detergents
Saturday, September 24, 2022 5:11 PM

Detergents improve the cleaning power of water

There are two types:

• Soaps
Made by the process of saponification in which fats and oils are hydrolysed by boiling
with concentrated NaOH

Fat / Oil + NaOH -> sodium salt of organic acid (soap) + Glycerol

A soap is the salt of a long chained organic acid.

• Soapless Detergents
Made by reacting hydrocarbons from petroleum with concentrated sulphuric acid. The
product is neutralised with NaOH to form a salt with a long hydrocarbon chain. E.g.
C18H29OSO3Na.

Detergents are composed of 2 parts: a polar head, and a long, non-polar, hydrocarbon tail.

Detergents do 2 things:
• It forms and interface between water and the fabric to improve wetting ability of the
water
• The non-polar tail dissolves in the dirt, and polar head dissolves in the water. The soap
particles are able to surround an lift the dirt off the fabric.

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