The Phenyl Group

As mentioned previously, the phenyl group (Ph-R, C₆H₅-R) can be formed by removing a hydrogen from benzene and attaching a substituent to where the hydrogen was removed. To this phenomenon, we can name compounds formed this way by applying this rule: (phenyl + substituent). For example, a chlorine attached in this manner would be named phenyl chloride, and a bromine attached in this manner would be named phenyl bromide. (See below diagram)

Figure 1. Naming of Phenyl Chloride and Phenyl Bromide

While compounds like these are usually named by simple benzene type naming (chlorobenzene and bromobenzene), the phenyl group naming is usually applied to benzene rings where a substituent with six or more carbons is attached, such as in the diagram below.

Figure 2. Diagram of 2-phenyloctane.

Although the diagram above might be a little daunting to understand at first, it is not as difficult as it seems after careful analysis of the structure is made. By looking for the longest chain in the compound, it should be clear that the longest chain is eight (8) carbons long (octane, as shown in green) and that a benzene ring is attached to the second position of this longest chain (labeled in red). As this rule suggests that the benzene ring will act as a function group (a substituent) whenever a substituent of more than six (6) carbons is attached to it, the name "benzene" is changed to phenyl and is used the same way as any other substituents, such as methyl, ethyl, or bromo. Putting it all together, the name can be derived as: 2-phenyloctane (phenyl is attached at the second position of the longest carbon chain, octane).

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مواضيع ذات صلة

Diastereotopic protons in acyclic compounds

Spotting diastereotopic protons in the NMR spectrum

How to tell if protons are homotopic, enantiotopic, or diastereotopic

The size of the geminal coupling constant

Geminal (2J) coupling

Heteroatoms in rings have axial and equatorial lone pairs

Four-membered rings

Ring size and NMR

Baldwin’s rules and ring opening

Combatting ΔS‡—the Thorpe–Ingold effect

Thermodynamic control over ring size

Making heterocycles: ring-closing reactions