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Difference Between Phenol, Phenyl, Benzene, Benzyl, and Aryl

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It is easy to identify the simplest aromatic hydrocarbon Benzene that is made of only two atoms- Carbon and hydrogen. Benzene is a planar, cyclic ring molecule with six sides. It has an alternating double bond that contributes to its extra stability by endowing it with resonance, a phenomenon of electron delocalization.  The molecular formula of Benzene is C6H6 and the structure is-

Structure of Benzene

Removing one hydrogen of the Benzene gives a phenyl (Ph-) group, written as C6H5-. If the lost hydrogen is replaced with Chloro, it becomes phenyl chloride (or chlorobenzene). On using phenyl as a side chain for propane, we get 1-phenylpropane. Replacement of two hydrogens of methane with phenyl group gives diphenylmethane.

difference between phenyl and benzene
 

When one hydrogen of the benzene ring is replaced with a hydroxy/alcohol functional group (-OH), the molecule obtained is a called phenol (combination of phenyl and alcohol). Therefore, phenol is the hydroxy derivative of benzene having the molecular formula C6H5-OH.  

structure of phenol

 

Adding one-Carbon linker (methylene, -CH2-) to the phenyl gives a benzyl group (C6H5-CH2- or Ph-CH2-) abbreviated as Bn. The methylene can be monosubstituted (C6H5-CHR-) or disubstituted (C6H5-CR2-). 

    Bn= C6H5-CH2- or Ph-CH2-

 

If the functional group present at the end of the alkyl chain is an amine, the molecule is called benzylamine (Bn-NH2). Other examples of different functional groups are benzyl alcohol (Bn-OH), benzyl bromide (Bn-Br), benzyl methyl ether (Bn-O-CH3), etc.

difference between benzene and benzyl
 

All the molecules encountered in the early examples are Benzene derivatives. However, for other non-benzene molecules displaying aromaticity (similar properties of planarity and resonance), in that case, such a molecule is simply referred to as an Aryl and is written as an Ar-.

The aryl group can be benzene, substituted benzenes, benzene with heteroatoms of N, S, O, naphthalene, other heteroaromatic compounds of thienyl, indolyl, etc. A few examples of aryl groups are-

difference between aryl and benzene and phenyl
 
 
 
Among phenol, phenyl, benzene, benzyl, and aryl, only phenol and benzene are complete structures. Whereas aryl, phenyl, benzyl are groups or side-chain substituents forming only a part of the entire molecule.  
 
 
Difference between phenol, phenyl, benzene, benzyl and aryl
 

 

 

Shown below are all the groups in one hypothetical structure-

 

examples of phenyl, phenol, aryl, benzene and benzyl
 
 

Sibi Atul

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Sibi Atul holds an M.Sc. in Drug Chemistry and spent several years as a Research Scientist in medicinal chemistry before moving into undergraduate teaching. She now writes and edits full-time at CurlyArrows — an organic chemistry platform trusted by learners in over 170 countries for more than 11 years — where she has authored hundreds of illustrated tutorials, Q&As, and course modules. She also hosts the podcast Learning Organic Chemistry with Sibi. Her drug discovery background and classroom experience uniquely qualify her to make complex chemistry accessible to students worldwide. Connect with Sibi on LinkedIn

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