By Thomas L Lemke
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Extra resources for Review of organic functional groups : introduction to medicinal organic chemistry
Example text
Phenol has Ihis ability ane! can Iherefore be considered an acid . r ee Fig. 7-2). If Kl is m ueh grcate r than K_I ' a strong acid c rists, while if K1 is s malle r Ihan K_I ' a wea k acid resulls. The faclor t lml influe nces Ihe mlio of K1 lo K_I is Ihe stability of Ihe :mio n fo rmed (in this case Ihe phenolale aníon ). rons on the o"'ygen \vi th Ihe d e locruized c10uJ of e lectrons ¡¡hove and below lhe aromalíc ríng; see Fig. 7-2). This is some lhing an alcoho l cannol do because un alcohol h)'droxyl is nol adjacent 10 an aromatic syste m, und resonance slabilization cloes no!
Phenols diffe r fmm alcohols by havi ng the O H group attached directly lo an aromatic ringo The nomellclature of the phellols is not as s)'stematic as has been the case witll the previous fu nctional groups. In many cases, phenols are named as suhstituted phenols using the common ortho, meta, or para nomenclature fO T the location of Ihe substiluents, or Ihe official nomenclature, in which Ihe ring is numbered, wilh the carbon thal bears Ihe OH being assigned the 1 position (Fig. 7-1). In phenol Ilomenclature, comlllon llames are often used, such as cresol, enlechol, and resorcinol.
X'lsition. It will be noled tha! Ihis is jusi Ihe opposite of phenols. With ortllo-substituled aniHnes, predictability fails becallse of intmmolecular interactions. "lSic. one would c: