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===Deprotonation=== With aqueous [[pKa|p''K''<sub>a</sub>]] values of around 16β19, alcohols are, in general, slightly weaker [[acid]]s than [[water]]. With strong bases such as [[sodium hydride]] or [[sodium]] they form [[Salt (chemistry)|salt]]s{{efn|Although commonly described as "salts", alkali metal alkoxides are actually better described structurally as oligomeric clusters or polymeric chains. For instance, potassium ''tert''-butoxide consists of a cubane-like tetramer, {{chem2|[''t''\-BuOK]4}}, that persists even in polar solvents like THF.}} called ''[[alkoxide]]s'', with the general formula {{chem2|RO-M+}} (where R is an [[alkyl]] and M is a [[metal]]). :{{chem2 | R\sOH + NaH -> R\sO-Na+ + H2 }} :{{chem2 | 2 R\sOH + 2 Na -> 2 R\sO-Na+ + H2 }} The acidity of alcohols is strongly affected by [[solvation]]. In the gas phase, alcohols are more acidic than in water.<ref>{{March6th|mode=cs1}}</ref> In [[DMSO]], alcohols (and water) have a p''K''<sub>a</sub> of around 29β32. As a consequence, alkoxides (and hydroxide) are powerful bases and nucleophiles (e.g., for the [[Williamson ether synthesis]]) in this solvent. In particular, {{chem2|RO-}} or {{chem2|HO-}} in DMSO can be used to generate significant equilibrium concentrations of acetylide ions through the deprotonation of alkynes (see [[Favorskii reaction]]).<ref>{{cite journal|last1=Ahmed|first1=Jasimuddin|last2=Swain|first2=Asim Kumar|last3=Das|first3=Arpan|last4=Govindarajan|first4=R.|last5=Bhunia|first5=Mrinal|last6=Mandal|first6=Swadhin K.|date=14 November 2019|title=A K-arylacetylide complex for catalytic terminal alkyne functionalization using KOtBu as a precatalyst|url=https://pubs.rsc.org/en/content/articlelanding/2019/cc/c9cc07833a|journal=Chemical Communications|language=en|volume=55|issue=92|pages=13860β13863|doi=10.1039/C9CC07833A|pmid=31670328|s2cid=204974842|issn=1364-548X}}</ref><ref>{{cite patent|number=WO1994012457A1|title=Process for preparing tertiary alkynols|gdate=1994-06-09|invent1=Babler|inventor1-first=James H.|url=https://patents.google.com/patent/WO1994012457A1/en}}</ref>
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