Editing Phenol (section)

===Reactions===
[[File:Hockpart2.svg|class=skin-invert-image|thumb|right|The Hock process leading to phenol via [[autoxidation]] of cumene.]]
[[File:Phenol-elpot-3D-vdW.png|right|thumb|[[Polar surface area]] of a "neutral" phenol substructure "shape". An image of a computed electrostatic surface of neutral phenol molecule, showing neutral regions in green, electronegative areas in orange-red, and the electropositive phenolic proton in blue.]]
[[File:Phenol in water.PNG|class=skin-invert-image|thumb|right|Phenol water phase diagram: Certain combinations of phenol and water can make two solutions in one bottle.]]

Phenol is highly reactive toward [[electrophilic aromatic substitution]]. The enhanced nucleophilicity is attributed to donation [[pi electron]] density from O into the ring. Many groups can be attached to the ring, via [[halogenation]], [[acylation]], [[sulfonation]], and related processes. 

Phenol is so strongly activated that bromination and chlorination lead readily to polysubstitution.<ref>{{Ullmann|vauthors=Muller F,  Caillard L |title=Chlorophenols|year=2011|doi=10.1002/14356007.a07_001.pub2}}</ref> The reaction affords 2- and 4-substituted derivatives. The regiochemistry of halogenation changes in strongly acidic solutions where {{chem2|PhOH2]+}} predominates. Phenol reacts with dilute nitric acid at room temperature to give a mixture of 2-nitrophenol and 4-nitrophenol while with concentrated nitric acid, additional nitro groups are introduced, e.g. to give [[Picric acid|2,4,6-trinitrophenol]].  [[Friedel Crafts alkylation]]s of phenol and its derivatives often proceed without catalysts.  Alkylating agents include alkyl halides, alkenes, and ketones.  Thus, [[1-Bromoadamantane|adamantyl-1-bromide]], [[dicyclopentadiene]]), and [[cyclohexanone]]s give respectively 4-adamantylphenol, a bis(2-hydroxyphenyl) derivative, and a 4-cyclohexylphenols.  [[Alcohol (chemistry)|Alcohol]]s and [[hydroperoxide]]s alkylate phenols in the presence of [[solid acid]] [[catalyst]]s (e.g. certain [[zeolite]]).  [[Cresol]]s and cumyl phenols can be produced in that way.<ref name=reddy>{{cite book|title=The Chemistry of Phenols|editor=Zvi Rappoport |series = PATAI'S Chemistry of Functional Groups | chapter=Electrophilic reactions of phenols |doi=10.1002/0470857277.ch9|year=2003 |publisher =John Wiley & Sons|author=V. Prakash Reddy. G. K. Surya Prakash|pages=605–660 |isbn=0471497371 }}</ref>

Aqueous solutions of phenol are weakly acidic and turn blue litmus slightly to red. Phenol is neutralized by [[sodium hydroxide]] forming sodium phenate or phenolate, but being weaker than [[carbonic acid]], it cannot be neutralized by [[sodium bicarbonate]] or [[sodium carbonate]] to liberate [[carbon dioxide]].
:{{chem2|C6H5OH + NaOH -> C6H5ONa + H2O}}

When a mixture of phenol and [[benzoyl chloride]] are shaken in presence of dilute [[sodium hydroxide]] solution, [[phenyl benzoate]] is formed. This is an example of the [[Schotten–Baumann reaction]]:
:{{chem2|C6H5COCl  + HOC6H5 -> C6H5CO2C6H5 + HCl}}

Phenol is reduced to [[benzene]] when it is distilled with [[zinc]] dust or when its vapour is passed over granules of zinc at 400&nbsp;°C:<ref>{{cite book|last=Roscoe|first=Henry|title=A treatise on chemistry, Volume 3, Part 3|year=1891|publisher=Macmillan & Co.|location=London|pages=23|url=https://books.google.com/books?id=HEY9AAAAYAAJ&q=zinc&pg=PA199}}</ref>
:{{chem2|C6H5OH + Zn -> C6H6 + ZnO}}

When phenol is treated with [[diazomethane]] in the presence of [[boron trifluoride]] ({{chem2|BF3}}), [[anisole]] is obtained as the main product and nitrogen gas as a byproduct.
:{{chem2|C6H5OH + CH2N2 -> C6H5OCH3 + N2}}

Phenol and its derivatives react with iron(III) chloride to give intensely colored solutions containing phenoxide complexes.