CBSE · Class 12 · Chemistry · Alcohols, Phenols and EthersDiscuss the mechanism of acid-catalyzed hydration of alkenes to yield alcohols. Include all the steps involved, stating clearly the role of each step in the reaction pathway.
Step-by-Step Solution
Introduction to Acid-Catalyzed Hydration\nAlkenes react with water in the presence of acid as a catalyst to form alcohols. This reaction follows Markovnikov's rule. The mechanism proceeds in three fundamental steps.
Step-by-Step Mechanism
Step 1: Protonation of alkene to form carbocation\nThe acid catalyst ($H_2SO_4$ or $H^+/H_2O$) dissociates to provide a proton ($H^+$, which exists as a hydronium ion, $H_3O^+$). The alkene acts as a nucleophile and attacks the hydronium ion to form a carbocation.
$$\text{CH}_3-\text{CH}=\text{CH}_2 + \text{H}_3\text{O}^+ \rightarrow \text{CH}_3-\text{CH}^+-\text{CH}_3 + \text{H}_2\text{O}$$\nThis is the slowest step and hence acts as the rate-determining step of the reaction.
Step 2: Nucleophilic attack of water on carbocation\nThe carbocation formed in the first step is electrophilic in nature. A water molecule, acting as a nucleophile, attacks the carbocation to form a protonated alcohol (oxonium ion).
$$\text{CH}_3-\text{CH}^+-\text{CH}_3 + \text{H}_2\text{O} \rightarrow \text{CH}_3-\text{CH}(\text{OH}_2^+)-\text{CH}_3$$
Step 3: Deprotonation to form alcohol\nThe protonated alcohol loses a proton ($H^+$) to another water molecule to yield a neutral alcohol molecule and regenerate the hydronium ion (catalyst).
$$\text{CH}_3-\text{CH}(\text{OH}_2^+)-\text{CH}_3 + \text{H}_2\text{O} \rightarrow \text{CH}_3-\text{CH}(\text{OH})-\text{CH}_3 + \text{H}_3\text{O}^+$$
Conclusion\nThus, through these three steps, the alkene is successfully converted into a corresponding alcohol following Markovnikov's addition of water.
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