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My class 12 chemistry textbook says that phenol molecule has three reactive sites or it's functionality is three. But I am confused whether it is so or not, because, what I know, phenol has three double bonds, it must have a functionality of six. Besides, it also has an -OH which is yet another reactive site, so in all making it seven. Please help so that I may have a clear understanding of how to judge functionality of a monomer molecule.

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    $\begingroup$ Could you quote the original text? $\endgroup$ – DHMO Oct 15 '16 at 6:41
  • $\begingroup$ "The functionality of ethene, vinyl chloride and styrene is 2 because these molecules have 2 reactive sites whereas the functionality of glycerol and phenol is three because they have three reactive sites." $\endgroup$ – ami_ba Oct 15 '16 at 6:52
  • $\begingroup$ Could you quote the whole section/paragraph? $\endgroup$ – DHMO Oct 15 '16 at 6:53
  • $\begingroup$ "Functionality of a monomer is the number of bonding sites in it. For example, the functionality of ethene, vinyl chloride and styrene is 2 because these molecules have 2 reactive sites whereas the functionality of glycerol and phenol is three because they have three reactive sites." $\endgroup$ – ami_ba Oct 15 '16 at 6:56
  • $\begingroup$ Maybe it's talking about this polymer of phenol, where indeed phenol only opens the ortho- and the para- sites. $\endgroup$ – DHMO Oct 15 '16 at 7:02
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Phenol has $3$ double-bond-equivalent, but not $3$ localized double bonds:

Look at its resonance structure:

Courtesy Wikipedia.

Therefore, to a electrophile, there are $3$ reaction sites, which are the ortho- and the para- positions.

A nuecleophile does not attack phenol.

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