Textbook Question
What is the major product obtained from the acid-catalyzed hydration of each of the following alkenes?
a. CH3CH2CH2CH=CH2
10. Addition Reactions
Acid-Catalyzed Hydration
3:25 minutesProblem 39a
Textbook Question
Provide the expected product for the reaction of each of the following alkenes with H2SO4 and H2O.
(a) 
Verified step by step guidance1
Step 1: Understand the reaction mechanism. The reaction involves the addition of water (H₂O) in the presence of sulfuric acid (H₂SO₄) to an alkene. This is an example of an acid-catalyzed hydration reaction, which follows Markovnikov's rule.
Step 2: Identify the alkene structure. Analyze the given alkene to determine the position of the double bond and the substituents attached to the carbon atoms involved in the double bond.
Step 3: Protonation of the alkene. The first step in the mechanism is the protonation of the double bond by H⁺ from H₂SO₄, forming a carbocation intermediate. Use Markovnikov's rule to predict which carbon will bear the positive charge (the more substituted carbon is favored).
Step 4: Nucleophilic attack by water. The carbocation intermediate is attacked by a water molecule, leading to the formation of an oxonium ion (R-CH₂-OH₂⁺).
Step 5: Deprotonation. The oxonium ion loses a proton (H⁺), resulting in the formation of the final alcohol product. Ensure the product aligns with Markovnikov's rule, where the hydroxyl group (-OH) is added to the more substituted carbon of the original double bond.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Addition
Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes. In the presence of strong acids like H₂SO₄, the double bond of the alkene acts as a nucleophile, attacking the electrophilic hydrogen, leading to the formation of a carbocation intermediate. This step is crucial for understanding how alkenes react with acids and water.
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Carbocation Stability
Carbocation stability is a key concept in predicting the outcome of reactions involving alkenes. Carbocations are positively charged species that can vary in stability based on their structure; tertiary carbocations are more stable than secondary or primary ones due to hyperconjugation and inductive effects. Understanding the stability of carbocations helps in determining the major product formed during the reaction with H₂SO₄ and H₂O.
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Hydration Reaction
The hydration reaction involves the addition of water (H₂O) to an alkene, resulting in the formation of an alcohol. In the context of the reaction with H₂SO₄, the acid protonates the alkene to form a carbocation, which then reacts with water to yield the alcohol product. This process is essential for converting alkenes into alcohols and is a common transformation in organic synthesis.
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