Vivian Marlowe
Alcohol is an organic compound with a hydroxyl (OH) functional group on an aliphatic carbon atom. The hydroxyl group is the functional group of all alcohols, which is why they are often represented by the general formula ROH, where R is an alkyl group. Alcohols are classified as primary, secondary, or tertiary, depending on which carbon of the alkyl group is bonded to the hydroxyl group. The reactivity hotspot in alcohols is the OH group, which can form hydrogen bonds with most other compounds.
| Characteristics | Values |
|---|---|
| Definition | Any of a class of organic compounds characterised by one or more hydroxyl (―OH) groups attached to a carbon atom of an alkyl group (hydrocarbon chain) |
| IUPAC Name | Alcohols are named by changing the ending of the parent alkane name to -ol |
| Chemical Formula | ROH, where R is an alkyl group |
| Classification | Primary, secondary, or tertiary, according to which carbon of the alkyl group is bonded to the hydroxyl group |
| State | Most alcohols are colourless liquids or solids at room temperature |
| Solubility | Alcohols of low molecular weight are highly soluble in water; with increasing molecular weight, they become less soluble in water |
| Boiling Point | Higher than comparable hydrocarbons and ethers due to hydrogen bonding |
| Uses | Sweeteners, perfumes, toiletries, pharmaceuticals, industrial chemicals, fuels, sterilising hospital instruments |
| Examples | Methanol, ethanol, propanol, 1-butanol, fatty alcohol, ethylene glycol |
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Methanol
The hydroxyl group is the functional group of the alcoholic family. The term alcohol originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. However, methanol, also known as methyl alcohol and wood spirit, is the simplest aliphatic alcohol. It is a light, volatile, colourless, and flammable liquid with a distinctive alcoholic odour similar to ethanol.
The chemical formula for methanol is CH3OH, which consists of a methyl group linked to a polar hydroxyl group. It is produced by the hydrogenation of carbon monoxide, and it has a variety of applications, including the production of formaldehyde, acetic acid, and methyl tert-butyl ether. Methanol is also used as a fuel additive and in the production of fuels for cars and ships.
The ancient Egyptians used methanol in their embalming process, obtaining it from the pyrolysis of wood. The modern synthetic production of methanol was first achieved by French chemist Paul Sabatier in 1905, who suggested reacting carbon dioxide and hydrogen to produce methanol. Today, methanol production has become more efficient through the use of catalysts, particularly copper, which enable lower-pressure operations.
While methanol is the most common industrial alcohol, it is important to note that it is more toxic than other simple alcohols. Its metabolism is affected by the presence of ethanol, which has a higher affinity for liver alcohol dehydrogenase. This results in the excretion of methanol intact in urine.
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Phenol
The term "alcohol" originally referred to the primary alcohol ethanol (ethyl alcohol), which is used as a drug and is the main alcohol present in alcoholic drinks. Alcohols are generally weak acids whose most acidic proton is the H of the OH group, which acts as the reactivity hotspot.
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Primary, secondary and tertiary alcohols
Alcohols are organic compounds characterised by one, two, or more hydroxyl groups (–OH) attached to the carbon atom in an alkyl group or hydrocarbon chain. The suffix '-ol' appears in the International Union of Pure and Applied Chemistry (IUPAC) chemical name of all substances where the hydroxyl group is the functional group with the highest priority. Alcohols are differentiated based on the presence and location of this hydroxyl group, which changes the physical and chemical properties of the alcohol.
There are three types of alcohols: primary, secondary, and tertiary alcohols. Primary alcohols are those where the carbon atom of the hydroxyl group is attached to only one alkyl group. Some examples of primary alcohols include methanol (propanol), ethanol, etc. Chemists count methanol as a primary alcohol despite it having no alkyl groups attaching to the carbon with the OH group. The term alcohol originally referred to the primary alcohol ethanol, which is the main alcohol present in alcoholic drinks.
Secondary alcohols are those where the carbon atom of the hydroxyl group is attached to two alkyl groups on either side. The two alkyl groups may be either structurally identical or different. Secondary alcohols will only produce ketones upon oxidation.
Tertiary alcohols are those that feature a hydroxyl group attached to the carbon atom, which is connected to three alkyl groups. The physical properties of these alcohols mainly depend on their structure. The presence of the -OH group allows the alcohols to form hydrogen bonds with their neighbouring atoms. However, tertiary alcohols will not undergo oxidation as the carbon with the OH group isn't attached to any removable hydrogen atom.
Alcohols can be produced using either an SN1 or SN2 substitution reaction. An SN1 reaction typically yields a tertiary alcohol, while an SN2 reaction typically yields a primary alcohol. Alcohols have a wide range of uses, including in beverages, as anti-freezing agents, as antiseptic agents, and as fuels.
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Ethanol
The term "alcohol" originally referred to the primary alcohol ethanol, also known as ethyl alcohol. Ethanol is a colourless liquid with a slight odour that burns with a smokeless blue flame. It is a compound consisting of an alkyl group with two carbon atoms, having a single bond between them, and an attached −OH functional group (also known as a hydroxyl group). The systematic name was defined by the International Union of Pure and Applied Chemistry (IUPAC), with the suffix "-ol" indicating that the hydroxyl group is the functional group with the highest priority.
The chemical formula for ethanol is CH3CH2OH, indicating the presence of a methyl group (CH3), a methylene group (CH2), and a hydroxyl group (OH). The hydroxyl group contributes significantly to ethanol's physical properties, making it more viscous and less volatile compared to similar compounds. Ethanol's boiling point is higher than comparable hydrocarbons and ethers due to hydrogen bonding. It is miscible in water, and its metabolism is influenced by the presence of liver alcohol dehydrogenase.
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Esterification
The esterification reaction is the inverse of the saponification reaction. In the presence of an acid, a carboxylic acid and an alcohol react to form an ester. Conversely, an ester reacts with a strong base or an acid to produce an alcohol and carboxylic acid in the saponification reaction.
- The reaction between alcohol and acid anhydride: This reaction is comparatively slower than the reaction between alcohol and acid chloride. To obtain a higher number of esters, the mixture must be warmed.
- The reaction between alcohol and acid chloride: This reaction can occur at room temperature. The ester is obtained with steamy acidic fumes of hydrogen chloride.
- The reaction between carboxylic acid and alcohol: This reaction requires an acid catalyst and heat to occur.
The two major uses of the esterification reaction are in the manufacturing of medicines and the manufacturing of paints and dyes.
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Frequently asked questions
The functional group of the alcoholic family is the hydroxyl (OH) group.
The International Union of Pure and Applied Chemistry (IUPAC) states that alcohols are named by changing the ending of the parent alkane name to -ol. The suffix -ol in non-IUPAC names, such as paracetamol or cholesterol, also typically indicates that the substance is an alcohol.
The hydroxyl group in ethanol (or ethyl alcohol) is represented by the alkyl group —CH2CH3. The hydroxyl group in methanol (CH3OH) and ethanol (CH3CH2OH) can also be seen in the first two members of the homologous series of alcohols.
The hydroxyl group makes alcohols polar, allowing them to form hydrogen bonds with one another and with most other compounds. This results in higher boiling points and increased water solubility compared to simple hydrocarbons.
