Wize University Organic Chemistry Textbook > Electrophilic Addition Reactions to Alkenes/Alkynes
Acid-Catalyzed Hydration
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Acid-catalyzed Hydration
Acid-catalyzed hydrations reactions:
- occur in multiple steps and are classified as an "ionic" reactions
- proceed via a carbocation intermediate
- have Markovnikov addition for a regiochemical outcome (Markovnikov addition has the higher priority group added to the more substituted carbon atom)
- have addition at the carbocation intermediate from top and bottom face with 50/50 distribution to give mixed sterechemical distribution (a racemic mixture if there is only one stereocentre)
Wize Concept
A hydration reaction means the addition of water (H2O).
Wize Tip
Typical strong acids used are sulfuric acid (H2SO4) and hydrochloric acid (HCl)
Steps of a Acid-catalyzed hydrations reaction:
- addition of the hydrogen atom from the acid to the alkene to generate a carbocation
- there may be carbocation rearrangement
- nucleophilic attack of the water nucleophile onto the carbocation
- deprotonation of the OH2+ group to regenerate the catalyst and generate the OH group
Mechanism:
Example: predict the product of the following acid-catalyzed hydration reaction below.
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Example: Acid-catalyzed Hydration
Draw a mechanism for the following intramolecular acid-catalyzed hydration reaction.
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Example: Acid-catalyzed Hydration
Predict the product(s) of the following acid-catalyzed hydration reactions.
