Lena Savoie
Benzene is a fundamental aromatic compound with unique naming conventions. An alcohol group attached to benzene is called phenol. The naming of substituted benzene compounds depends on the number of substituents present. For monosubstituted benzene, no location is necessary; for example, methylbenzene is simply called toluene. However, for disubstituted benzene, specific terms are used to indicate the relative positions of the substituents: ortho (O): substituents are adjacent (1,2-position); meta (M); and para (P). For three or more substituents, numerical locations are necessary.
| Characteristics | Values |
|---|---|
| Common name for compound | Hydroxyquinol |
| IUPAC name | Benzene-1,2,4-triol |
| Traditional name | Pyrocatechol |
| Name when OH group attached to benzyl group | Benzyl alcohol |
| Name when OH group attached to phenyl group | Phenol |
| Name when OH group attached to benzene ring | Phenol |
| Name when two hydroxyl groups on adjacent carbons of benzene | Catechol |
| Name when chlorine attached to phenyl group | Chlorobenzene |
| Name when chlorine attached to benzyl group | Benzyl chloride |
| Name when two substituents on benzene ring | Ortho- (o-), meta- (m-), para (p)-) |
| Name when three or more substituents on benzene ring | Numerical locations |
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What You'll Learn
- The alcohol group attached to benzene is called phenol
- The IUPAC name for benzene with three alcohol groups is benzene-1,2,4-triol
- The common name for the same compound is hydroxyquinol
- When numbering the ring, give substituents the smallest possible number?
- If the alkyl group attached to benzene has seven or more carbons, the compound is named as a phenyl-substituted alkane
The alcohol group attached to benzene is called phenol
Benzene is a fundamental aromatic compound that serves as a cornerstone in organic chemistry. Its unique structure and historical significance make it essential to master its naming conventions, which can be quite distinct and sometimes perplexing. Benzene derivatives have specific common names based on the attached functional groups. For instance, an alcohol group attached to benzene is called phenol.
Phenol is a functional group or class of molecules with one or more hydroxy groups attached to a benzene or other arene ring. Phenol is also the name of the molecule formed when an OH group is bonded to a benzene ring. The OH group reacts in the same way as phenol due to its position on the benzene ring.
The naming of substituted benzene compounds depends on the number of substituents present. For monosubstituted benzene, no location is necessary. For example, methylbenzene is simply called toluene. However, for disubstituted benzene, specific terms are used to indicate the relative positions of the substituents. Ortho (O), Meta (M), and Para (P) are used instead of numbers. For three or more substituents, numerical locations are necessary.
The common name for the compound is hydroxyquinol, which is still in common use. The other two isomers of benzenetriol also have non-IUPAC-approved common names that are widely used. They are phloroglucinol for benzene-1,3,5-triol and pyrogallol for benzene-1,2,3-triol.
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The IUPAC name for benzene with three alcohol groups is benzene-1,2,4-triol
Benzene is a fundamental aromatic compound with unique naming conventions. Its derivatives include phenyl (alcohol), toluene (methyl), aniline (amino), benzoic acid (carboxylic acid), and benzaldehyde (aldehyde). Each derivative has a specific name, often stemming from Greek or Latin roots.
An alcohol group attached to benzene is called phenol, which is the preferred IUPAC name. The structure is substitutable at any position, and locants 2, 3, and 4 are recommended. When an OH group is added to the benzene ring, benzene no longer serves as a base. The carbon where the substituent is attached on the base will be given the first priority and named as carbon #1 (C1). The rest of the substituents are then given the lowest numbering.
Benzene derivatives with two or more hydroxyl groups are named by adding the suffix 'ol' to the end of the word 'benzene' and numbering the carbons where the hydroxyl groups are attached. For example, benzene with two hydroxyl groups on adjacent carbons is called catechol. When there are three hydroxyl groups, the suffix becomes 'triol'.
Therefore, the IUPAC name for benzene with three alcohol groups is benzene-1,2,4-triol. The textbook may also give the name 1,2,4-trihydroxybenzene, using the hydroxyl groups as substituents. The other two isomers of benzenetriol have non-IUPAC-approved common names: phloroglucinol for benzene-1,3,5-triol and pyrogallol for benzene-1,2,3-triol.
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The common name for the same compound is hydroxyquinol
Benzene rings with an alcohol group attached are known as phenols. The position of the alcohol group is indicated by a number, with the carbon where the alcohol group is attached given the first priority and named as carbon #1 (C1). For example, when the hydroxyl group is attached to carbon #1, the compound is known as benzene-1-ol. When there are two or more hydroxyl groups, the compound is named according to the seniority order of classes, with the -OH substituent corresponding to the principal characteristic group expressed as a suffix ('ol'). For example, a compound with hydroxyl groups on carbons 1, 2, and 4 would be called benzene-1,2,4-triol.
The IUPAC name for this compound is benzene-1,2,4-triol. However, the common name for the same compound is hydroxyquinol. This name is still in common use, along with other non-IUPAC-approved common names for the isomers of benzenetriol: phloroglucinol for benzene-1,3,5-triol and pyrogallol for benzene-1,2,3-triol. These names are used far more frequently than "benzenetriol".
The naming of benzene rings and their derivatives is quite distinct and can be confusing. Benzene derivatives have specific common names based on the attached functional groups. For example, a methyl group attached to benzene is known as toluene, while an amino group is called aniline. The naming conventions and structural implications of benzene and its derivatives are vital for success in organic chemistry.
The compound 8-hydroxyquinoline (also known as oxine) is an organic compound derived from the heterocycle quinoline. It was first obtained by Hugo Weidel and his student Albert Cobenzl in 1880, who decarboxylated oxycinchoninic acid and characterized the compound as melting at about 70°C. They identified the hydroxy group on the benzene ring and called the compound oxyquinoline and α-quinophenol.
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When numbering the ring, give substituents the smallest possible number
When it comes to naming benzene rings, the priority of the substituents is key. The substituent with the highest priority will determine which carbon in the benzene ring is labelled as position 1. The carbon atom connected to the highest priority substituent is given the number 1, and the rest of the carbon atoms are numbered sequentially, moving around the ring in a way that gives the other substituents the smallest possible numbers.
The priority of substituents is based on their chemical hierarchy and, in the case of multiple groups with the same priority, alphabetical order. This is known as alphanumerical order, which involves ordering both letters and numbers. Non-italic Roman letters are considered first, unless they are used as locants or part of a compound or composite locant.
For monosubstituted benzene, no location is necessary. For example, methylbenzene is called toluene. However, for disubstituted benzene, specific terms are used to indicate the relative positions of the substituents. Ortho (O) refers to substituents that are adjacent (1,2-position), meta (M) refers to substituents that are one space apart (1,3-position), and para (P) refers to substituents that are two spaces apart (1,4-position). For disubstituted benzene, you can use ortho, meta, and para instead of numbers. For three or more substituents, numerical locations are necessary.
The naming of benzene derivatives also depends on the number of substituents present. An alcohol group attached to benzene is called phenol, a methyl group attached is known as toluene, an amino group is called aniline, a carboxylic acid group is called benzoic acid, an aldehyde group is called benzaldehyde, a methyl ketone group is called acetophenone, and two hydroxyl groups on adjacent carbons are called catechol.
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If the alkyl group attached to benzene has seven or more carbons, the compound is named as a phenyl-substituted alkane
Benzene is a fundamental aromatic compound with unique naming conventions. Aromatic compounds, more than any other class of organic compounds, have acquired a large number of nonsystematic names. While IUPAC rules discourage the use of most such names, they do allow some of the more widely used ones to be retained. For example, methylbenzene is known commonly as toluene, aminobenzene as aniline, and hydroxybenzene as phenol.
A compound containing a benzene ring with one or more alkyl substituents is called an arene. If the alkyl substituent is smaller than the ring (six or fewer carbons), the arene is referred to as an alkyl-substituted benzene. If the alkyl substituent is larger than the ring (seven or more carbons), the compound is referred to as a phenyl-substituted alkane. The name phenyl, pronounced fen-nil and sometimes abbreviated as Ph or Ф (Greek phi), is used for the –C6H5 unit when the benzene ring is considered a substituent. The word is derived from the Greek pheno (“I bear light”), commemorating the discovery of benzene by Michael Faraday in 1825 from the oily residue left by the illuminating gas used in London street lamps.
The naming of substituted benzene compounds also depends on the number of substituents present. For monosubstituted benzene, no location is necessary; for example, methylbenzene is simply called toluene. However, for disubstituted benzene, specific terms are used to indicate the relative positions of the substituents: Ortho (O): Substituents are adjacent (1,2-position). Meta (M): Substituents are in a 1,3 relationship. Para (P): Substituents are in a 1,4 relationship.
When the numbering system is used, the carbon where the substituent is attached on the base will be given the first priority and named as carbon #1 (C1). The normal priority rules then apply in the nomenclature process (give the rest of the substituents the lowest numbering as you could).
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Frequently asked questions
Phenol.
Some other names for this compound include hydroxyquinol, pyrogallol, and phloroglucinol.
The textbook example names this compound 1,2,4-trihydroxybenzene, but the preferred IUPAC name is benzene-1,2,4-triol.
