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hydration reaction wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 organic chemistry toggle organic chemistry subsection 1 1 epoxides to glycol 1 2 alkenes 1 3 alkynes 1 4 aldehydes and ketones 1 5 nitriles 2 inorganic and materials chemistry 3 see also 4 references 5 external links toggle the table of contents hydration reaction 36 languages العربية български bosanski català čeština deutsch esperanto español eesti فارسی suomi français gaeilge galego हिन्दी հայերեն bahasa indonesia italiano 日本語 қазақша 한국어 lietuvių bahasa melayu polski português română русский srpskohrvatski српскохрватски slovenčina slovenščina српски srpski தமிழ் türkçe українська oʻzbekcha ўзбекча 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikiquote wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction in which a substance combines with water in chemistry a hydration reaction is a chemical reaction in which a substance combines with water in organic chemistry water is added to an unsaturated substrate which is usually an alkene or an alkyne this type of reaction is employed industrially to produce ethanol isopropanol and butan 2 ol 1 organic chemistry edit any unsaturated organic compound is susceptible to hydration epoxides to glycol edit several million tons of ethylene glycol are produced annually by the hydration of oxirane a cyclic compound also known as ethylene oxide c 2 h 4 o h 2 o ho ch 2 ch 2 oh acid catalysts are typically used 2 alkenes edit the general chemical equation for the hydration of alkenes is the following rrc ch 2 h 2 o rrc oh ch 3 a hydroxyl group oh attaches to one carbon of the double bond and a proton h adds to the other the reaction is highly exothermic in the first step the alkene acts as a nucleophile and attacks the proton following markovnikov s rule in the second step an h 2 o molecule bonds to the other more highly substituted carbon the oxygen atom at this point has three bonds and carries a positive charge i e the molecule is an oxonium another water molecule comes along and takes up the extra proton this reaction tends to yield many undesirable side products for example diethyl ether in the process of creating ethanol and in its simple form described here is not considered very useful for the production of alcohol two approaches are taken traditionally the alkene is treated with sulfuric acid to give alkyl sulphate esters in the case of ethanol production this step can be written h 2 so 4 c 2 h 4 c 2 h 5 o so 3 h subsequently this sulphate ester is hydrolyzed to regenerate sulphuric acid and release ethanol c 2 h 5 o so 3 h h 2 o h 2 so 4 c 2 h 5 oh this two step route is called the indirect process in the direct process the acid protonates the alkene and water reacts with this incipient carbocation to give the alcohol the direct process is more popular because it is simpler the acid catalysts include phosphoric acid and several solid acids 1 here an example reaction mechanism of the hydration of 1 methylcyclohexene to 1 methylcyclohexanol hydration reaction mechanism from 1 methylcyclohexene to 1 methylcyclohexanol many alternative routes are available for producing alcohols including the hydroboration oxidation reaction the oxymercuration reduction reaction the mukaiyama hydration the reduction of ketones and aldehydes and as a biological method fermentation alkynes edit acetylene hydrates to give acetaldehyde 3 the process typically relies on mercury catalysts and has been discontinued in the west but is still practiced in china the hg 2 center binds to a c c bond which is then attacked by water the reaction is h 2 o c 2 h 2 ch 3 cho aldehydes and ketones edit aldehydes and to some extent even ketones hydrate to geminal diols the reaction is especially dominant for formaldehyde which in the presence of water exists significantly as dihydroxymethane conceptually similar reactions include hydroamination and hydroalkoxylation which involve adding amines and alcohols to alkenes nitriles edit nitriles are susceptible to hydration to amides rcn h 2 o rc o nh 2 this reaction requires catalysts enzymes are used for the commercial production of acrylamide from acrylonitrile citation needed inorganic and materials chemistry edit hydration is an important process in many other applications one example is the production of portland cement by the crosslinking of calcium oxides and silicates that is induced by water hydration is the process by which desiccants function cuso 4 5h 2 o is bright blue and has a rather different structure from its colourless anhydrous derivative anhydrous cuso 4 powder see also edit aquation references edit 1 2 falbe jürgen bahrmann helmut lipps wolfgang mayer dieter alcohols aliphatic ullmann s encyclopedia of industrial chemistry weinheim wiley vch doi 10 1002 14356007 a01_279 isbn 978 3 527 30673 2 siegfried rebsdat dieter mayer ethylene glycol ullmann s encyclopedia of industrial chemistry weinheim wiley vch doi 10 1002 14356007 a10_101 isbn 978 3 527 30673 2 marc eckert gerald fleischmann reinhard jira hermann m bolt klaus golka acetaldehyde in ullmann s encyclopedia of industrial chemistry 2006 wiley vch weinheim doi 10 1002 14356007 a01_031 pub2 external links edit wikiquote has quotations related to hydration reaction retrieved from https en wikipedia org w index php title hydration_reaction oldid 1363947391 categories addition reactions general chemistry hidden categories articles with short description short description matches wikidata all articles with unsourced statements articles with unsourced statements from march 2025 this page was last edited on 13 july 2026 at 13 53 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents hydration reaction 36 languages add topic