Lena Savoie
The terms primary, secondary, and tertiary are used to classify hydrocarbons, carbocations, alkyl halides, alcohols, amines, and amides. In the context of alcohols, these terms refer to the number of carbon atoms directly attached to the carbon atom bearing the hydroxyl group (also known as the carbinol carbon). A primary alcohol is attached to one carbon atom, a secondary alcohol is attached to two carbon atoms, and a tertiary alcohol is attached to three carbon atoms. Therefore, if an alcohol has one carbon atom and one hydroxyl group, it would be classified as a primary alcohol, not a secondary alkane.
| Characteristics | Values |
|---|---|
| Type of carbon | Secondary |
| Number of carbons attached to the carbon atom with OH group | 2 |
| General formula | R2CHOH |
| Name | Secondary (2°) alcohol |
| Oxidation product | Ketone |
| Boiling point | Higher than primary alcohol, lower than tertiary alcohol |
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What You'll Learn
Primary, secondary, tertiary, and quaternary hydrocarbons
The terms primary, secondary, tertiary, and quaternary refer to the number of carbon atoms directly attached to another carbon atom in hydrocarbons, carbocations, alkyl halides, alcohols, amines, and amides. These terms only apply to alkyl carbons and carbocations. When the carbon participates in pi-bonding, different names are used.
Primary carbons (1°) are attached to one other carbon and three hydrogens. They are also known as methyl (CH3) carbons. Secondary carbons (2°) are attached to two other carbons and two hydrogens. They are also known as methylene (CH2) carbons. Tertiary carbons (3°) are attached to three other carbons and one hydrogen. They are also known as methine (R3CH) carbons. Quaternary carbons (4°) are attached to four other carbons. It is not possible to have more than four substituents on a carbon atom, as this would violate the octet rule.
Primary, secondary, and tertiary alcohols are named according to the number of carbons directly attached to the carbon bearing the hydroxyl (-OH) group. A primary alcohol is attached to one other carbon atom, a secondary alcohol to two, and a tertiary alcohol to three. There is no such thing as a quaternary alcohol because that would require having five bonds to carbon.
The oxidation of primary alcohols forms aldehydes, while the oxidation of secondary alcohols forms ketones. Alcohols with two -OH groups on adjacent carbon atoms are commonly known as glycols. An example of a glycol is ethylene glycol, which is used in antifreeze.
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Primary, secondary, and tertiary alcohols
Alcohols are organic compounds characterised by one, two or more hydroxyl groups (OH) attached to a carbon atom in an alkyl group or hydrocarbon chain. Alcohols are classified as primary, secondary, or tertiary alcohols, depending on the number of carbons directly attached to the carbon bearing the hydroxyl group.
A primary (1°) alcohol is one in which the carbon atom with the OH group is attached to only one other carbon atom. Its general formula is RCH2OH. Some examples of primary alcohols include methanol (propanol) and ethanol.
A secondary (2°) alcohol is one in which the carbon atom with the OH group is attached to two other carbon atoms. Its general formula is R2CHOH. An example of a secondary alcohol is cyclohexanol. Secondary alcohols are oxidized to form ketones.
A tertiary (3°) alcohol is one in which the carbon atom with the OH group is attached to three other carbon atoms. Its general formula is R3COH. Examples of tertiary alcohols include 1,2,3-propanetriol (glycerin or glycerol).
The physical properties of these alcohols depend on their structure. The presence of the OH group allows alcohols to form hydrogen bonds with neighbouring atoms, which results in higher boiling points compared to alkanes. Alcohols with lower molecular weights tend to be highly soluble in water, while those with higher molecular weights become less soluble.
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How to define primary, secondary, and tertiary carbons
In organic chemistry, carbon atoms can be classified as primary, secondary, tertiary, or quaternary based on the number of additional carbon atoms bonded to the carbon atom of interest.
Primary carbon atoms are attached to one other carbon atom. They are denoted by 1° and have the chemical formula RCH2OH.
Secondary carbon atoms are attached to two other carbon atoms. They are denoted by 2° and have the chemical formula R2CHOH.
Tertiary carbon atoms are attached to three other carbon atoms. They are denoted by 3° and have the chemical formula R3COH.
Quaternary carbon atoms are attached to four other carbon atoms. They are denoted by 4°. It is important to note that quaternary carbons are not classified as alkyl carbons or carbocations. When the carbon participates in pi-bonding, different terminology is used.
This classification system is important in understanding the reactivity of hydrocarbons. For example, in the context of alcohols, the number of carbon atoms attached to the carbon bearing the hydroxyl group (also known as the carbinol carbon) determines whether the alcohol is primary, secondary, or tertiary.
Additionally, the terms primary, secondary, and tertiary are also used to classify other functional groups, such as alkyl halides and amines, based on the number of carbon atoms directly attached to the relevant atom (carbon for alkyl halides and nitrogen for amines).
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How to define primary, secondary, and tertiary alkyl halides
Alkyl halides are organic compounds that contain a halogen atom directly attached to an sp3 hybridized carbon atom. The terms primary (1°), secondary (2°), and tertiary (3°) are used to classify alkyl halides based on the number of carbons directly attached to the carbon atom bearing the halogen.
A primary alkyl halide is one where the carbon atom with the halogen group is attached to only one other carbon atom. These are the least substituted alkyl halides and are the most reactive.
Secondary alkyl halides have the halogen group attached to a carbon atom that is connected to two other carbon atoms. These are more substituted than primary alkyl halides and exhibit different reactivity patterns.
Tertiary alkyl halides are those where the carbon atom with the halogen group is attached to three other carbon atoms. These are the most substituted form of alkyl halides and have distinct chemical behaviours. For example, in solvolysis reactions, tertiary alkyl halides are favoured for the formation of alcohols or ethers.
The classification of alkyl halides as primary, secondary, or tertiary is similar to that of alcohols. Alcohols are organic compounds that contain one or more hydroxyl (-OH) groups. A primary alcohol has the -OH group on a carbon atom attached to a single carbon atom, while a secondary alcohol has the -OH group on a carbon atom attached to two other carbon atoms. A tertiary alcohol has the -OH group attached to a carbon atom that is connected to three other carbon atoms.
In summary, the definitions of primary, secondary, and tertiary alkyl halides are based on the number of carbon atoms directly attached to the carbon bearing the halogen. This classification system is also used for alcohols, where the number of carbon atoms attached to the carbon bearing the hydroxyl group determines the compound's designation.
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The difference between primary, secondary, and tertiary amines and amides
In organic chemistry, the terms primary, secondary, and tertiary are used to classify various types of compounds, including hydrocarbons, carbocations, alkyl halides, alcohols, amines, and amides. These classifications are based on the number of carbon atoms directly attached to a specific central atom within the compound.
Amines
Amines are derivatives of ammonia (NH3) where one or more of the hydrogen atoms are replaced by alkyl or aryl groups. The number of alkyl or aryl groups attached to the nitrogen atom determines whether an amine is primary, secondary, or tertiary.
- Primary amines have one alkyl or aryl group attached to the nitrogen atom.
- Secondary amines have two alkyl or aryl groups attached to the nitrogen atom.
- Tertiary amines have three alkyl or aryl groups attached to the nitrogen atom, resulting in no remaining hydrogen atoms bonded to the nitrogen.
Amides
Amides are similarly classified according to the number of carbon atoms attached to the nitrogen atom.
- Primary amides have the nitrogen atom bonded to one carbon atom, specifically the carbonyl carbon.
- Secondary amides have the nitrogen atom bonded to two carbon atoms.
- Tertiary amides have the nitrogen atom bonded to three carbon atoms.
It is important to note that the IUPAC (International Union of Pure and Applied Chemistry) definitions of primary, secondary, and tertiary amides differ from the definitions in colloquial use.
Alkane
While the terms primary, secondary, and tertiary are commonly used to classify various types of compounds in organic chemistry, they are not typically used to describe alkanes. Alkanes are hydrocarbons with the general formula CnH2n+2, and they are typically identified based on the number of carbon atoms they contain. However, in the context of alcohols, which are derivatives of hydrocarbons, the terms primary, secondary, and tertiary are used to describe the carbon atom's attachment to the hydroxyl group (-OH) rather than the carbon atom itself.
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Frequently asked questions
Primary, secondary, and tertiary alcohols are named according to the number of carbons directly attached to the carbon bearing the hydroxyl group. A primary alcohol is attached to one carbon, a secondary alcohol to two carbons, and a tertiary alcohol to three carbons.
Primary, secondary, tertiary, and quaternary alkyl carbons are defined according to the number of carbons directly attached to that carbon. Primary is attached to one carbon, secondary to two carbons, tertiary to three carbons, and quaternary to four carbons.
Primary alcohols are oxidized to form aldehydes, secondary alcohols are oxidized to form ketones, and tertiary alcohols show no reaction.
